Find Your Waterfront Oasis

Beautiful Waterways Abound...

The Chesapeake region is full of a variety of waterways to explore... kayaking, sailing, power sports, yachting and watching all the life that fills the areas. We live this life and know the areas and the unique characteristics of waterview and waterfront homes. Let us be your guide on this adventure!

there's no better way to ENJOY the water than to LIVE on the WATER

111 57th St Unit UNIT 303, Ocean City
$619,900
3 Beds ⋅ 2 Baths
Rare find! Pristine premium direct bayfront end unit with private wrap around balcony, smart home capibilities, freshly painted throughout, and private owners closet in a sought after boutique building. Enjoy the resort-style amenities that include a community pool, a sandy beach ideal for relaxing or grilling, community dock perfect for crabbing and fishing, and convenient kayak storage and launching facilities. Conveniently located the heart of midtown Ocean City. Just a short walk to the beach, restaurants, shopping, entertainment, and public transportation. This is a absolutely must see if your looking for a second home, investment, or rental property. The unit is unfurnished, offering the buyer a blank canvas to personalize and make it their own. Furnished photos in listing are virtually staged. Schedule your private showing today!

111 57th St Unit UNIT 303, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC. Contact:

966 Biddle St, Chesapeake City
$399,999
Take advantage of this opportunity to build your dream home on the breath taking 1.6 acre lot. This property features views of the canal and is just minutes from the historic town of Chesapeake City for all your dining, shopping, and entertainment needs. The land is also conveniently located near major roadways and Delaware for additional shopping and dining.

966 Biddle St, Chesapeake City

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

1131 Lake Shore Dr, Oakland
$3,950,000
8 Beds ⋅ 10 Baths
Experience exceptional lakefront living in this spectacular eight-bedroom estate designed for unforgettable gatherings and year-round enjoyment. Perfectly positioned on an oversized lakefront lot with 116’ LF, this remarkable home offers easy access to the water via a walking path, and the abundance of windows fill the interior with natural light. At the heart of the home is a magnificent great room with soaring ceilings, creating an impressive space for entertaining family and friends. The gourmet kitchen is a chef's dream, featuring premium finishes, generous prep space, and abundant cabinetry, making it as functional as it is beautiful. Boasting an indoor sparkling pool and sauna right off the lower-level family room, along with a full kitchen and a playroom. Then step outside to your private lakeside retreat, complete with two relaxing hot tubs, a fire pit area, a sports court in the front, and spacious outdoor living areas ideal for dining, entertaining, or simply soaking in the peaceful surroundings. With eight spacious en-suite bedrooms, there is ample room for guests, making this an exceptional primary residence, vacation home, or luxury rental opportunity “The Haven”. Offering the perfect blend of elegance, comfort, and resort-style amenities, this extraordinary waterfront property is a rare opportunity to own the ultimate lakefront lifestyle.

1131 Lake Shore Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

1107 Oyster Cove Dr, Grasonville
$759,000
3 Beds ⋅ 4 Baths
One of the BEST VIEWS in Oyster Cove! WATERFRONT VIEWS from almost every room! This beautiful, gated community at the Kent Narrows Bridge greets you with scenic entrance ponds and fountains. You feel like you are on vacation while you are working from your home office in this tranquil setting. Grill on your spacious deck while entertaining friends and watching boats heading to St. Michaels/Annapolis, etc. Freshly painted throughout with 3 bedrooms/3.5 baths. Hardwood floors are featured on the 1st/2nd floors plus a TV, FP w/electric insert and built-ins. The updated, eat-in country kitchen features granite counters, beadboard bar and white cabinetry. Waterfront primary suite has a balcony, barn doors, W-I shower, W-I closet and jacuzzi. Utility room is equipped with newer, front-loading washer/dryer. Enjoy the large deck with remote-controlled awning and gate. HWH and W/D 2022. Roof/siding 2019. HVAC 2018. Boat slips available for rent/sale, along with 5 visitor slips for your boating friends. Enjoy the 1.5 mi. WATERFRONT walking path and the beautiful clubhouse w/state-of-the-art gym, full kitchen, holiday parties and monthly socials, game nights, etc. Saltwater pool opens at 6AM so you can enjoy a swim before the heat of the day. Dock your boat in 1 of the 2 marinas where slips range from 35' - 60'. Use the convenient launch pad for your kayak where there is space for > 100 kayaks or take advantage of the 10 jet ski ports. Enjoy a bike ride on the nearby, paved Cross Island Trail from Oyster Cove to the Chesapeake Bay, Romancoke and Long Point Rd. Convenient for dog walking, biking, jogging, etc. Walk to 5 restaurants. Only 20 minutes to Annapolis by car or a 30-minute boat ride to St. Michael's for lunch and shopping. Enjoy a round of golf at Blue Heron executive course or Queenstown championship course. Your dream house awaits you!

1107 Oyster Cove Dr, Grasonville

Listing courtesy of Star Realty. Contact:

9308 Atlantic Ave, North Beach
$899,900
3 Beds ⋅ 3 Baths
Welcome to your stunning bayfront retreat in the heart of North Beach....an irresistible blend of luxury, charm, and coastal lifestyle. Whether you're looking for a full-time residence, a weekend retreat, or a year-round vacation getaway, this home delivers comfort, style, and that coveted small-town vibe. Step inside to find a beautifully designed interior featuring a spacious main level with a parlor/office area, two bedrooms, a full bath, and a bright great room with 9-foot ceilings, hardwood floors, and a cozy wood-burning fireplace with stone surround. Natural light pours in, and a back door leads to your private, fully fenced backyard, complete with an outdoor shower, wooden path, and ample space for gardening or gatherings. Upstairs, a gourmet kitchen with stainless steel appliances, a kitchen island, built-in dining nook with storage….and flows seamlessly into the open-concept family room. Here, large windows frame breathtaking bay views, and a welcoming balcony invites you to sip your morning coffee while watching the sunrise over the water. The upper level also includes a powder room, laundry area, and a spacious primary suite with dual closets and an en-suite bath. And the charm doesn’t stop inside....this home also features two front balconies perfect for taking in the coastal air, water views, and the sights and sounds of a vibrant waterfront community. A detached garage includes an absolutely adorable 1BR/1BA studio that is ideal for guests, an art studio, and/or a private office. But what truly sets this home apart is its unbeatable location in North Beach! A quaint, walkable waterfront town known for its welcoming boardwalk, lively seasonal events, and thriving food and music scene. Just steps from your front door, you’ll find award-winning restaurants, charming cafes, ice cream shops, lively bars, and live music venues that bring the town to life. Spend your evenings enjoying the buzz of local events or take a peaceful sunset stroll along the beach. This beautiful home is located within 2 miles of Herrington Harbour South Marina and Rod 'N' Reel Marina -- a perfect location for a recreational boater to enjoy access to the bay and all the associated amenities. You’re not just buying a house; you’re embracing a lifestyle where the bay is your backyard and everything you need is just a short walk away! Come experience the Chesapeake lifestyle—vacation every day in North Beach.

9308 Atlantic Ave, North Beach

Listing courtesy of CENTURY 21 New Millennium. Contact:

601 Bayshore Dr Unit 16, Ocean City
$1,499,000
4 Beds ⋅ 4 Baths
Experience luxury waterfront living in this one-of-a-kind, custom-built Bayfront residence located in the heart of Ocean City. Offered fully furnished, this exceptional 4-bedroom, 4.5-bath home showcases outstanding craftsmanship, premium finishes, and breathtaking panoramic bay views. Designed for both comfort and entertaining, the home features a private elevator, central air and heat, multiple ceiling fans, enhanced lighting throughout, and upgraded bamboo flooring. The first level offers a spacious living area along with a bedroom and full bath, making it ideal for guests, a home office, or flexible living space. A built-in Murphy bed provides additional convenience. The second floor includes two spacious bedrooms with sizable closet space, while the third level includes a luxurious primary suite with whirlpool tub and shower. Recent upgrades include new top-floor windows, a new refrigerator, microwave, and second-floor washer and dryer. The fully equipped gourmet kitchen features modern appliances and ample space for gathering with family and friends. A cozy fireplace allows for comfortable year-round enjoyment. Outdoor living is equally impressive with a private deep-water dock, wide fishing and crabbing pier, and an expanded waterfront deck offering direct bay access and some of the most magnificent sunset views in Ocean City. HOME FEATURE LIST Panoramic BAYFRONT VIEWS FROM ALL LEVELS Expanded private Bayfront deck -new 2024 Brand new electrical supply line service installed by Delmarva Power 2026 Exceptional Craftsmanship with premium finishes Gourmet Kitchen -New Refrigerator , Microwave 2026 , Granite countertops Full size Washer /Dryer 2025 Luxurious third floor Primary Master Suite with whirlpool tub and full shower Bamboo flooring and tile through out home New Carpet – Bedrooms -2026 Central A/C and Heat Elevator – serviced 2026 Sprinkler System – serviced and inspected 2026 Third floor all new windows - 2025 Magnified extended ceiling lighting Stamped Professional Art Drawings available for Expansion of home – NO HOA

601 Bayshore Dr Unit 16, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact:

3287 Marsh Rd, Ewell
$139,000
3 Beds ⋅ 1 Baths
Welcome to this lovely island waterfront home cherished by the same family since 1940 and originally built by the owner's father. This unique home is full of character and carefully cared for throughout the decades. A welcoming front porch sets the tone perfect for relaxing before stepping inside to the inviting family room. The living area is complete with original moldings and a pair of lovely wall sconces that provide a warm tone in the space. The efficient eat - in kitchen features custom-made cabinetry, including original tall base cabinets designed for added comfort while cooking. A vintage gas stove remains in working condition, and you'll find plenty of cabinet space with clever storage areas and a convenient pantry. The main level includes two comfortable bedrooms, one with water views, and the second features a custom built-in wall cabinet. The full bath showcases beautifully preserved original tile and a tub set in an elegant alcove with a window perfectly placed to capture serene water views. The spacious laundry room has a utility closet, a washer and dryer, large chest freezer, and a separate walk in shower stall. Upstairs, a bonus room with extra storage tucked under the eaves plus a separate room for another bedroom or flex space. Dormer windows bring in natural light and frame picturesqe water views of the Chesapeake Bay and surrounding marshes. Outside the beautifully maintained yard with sidewalks and chain-link fencing also includes an 12' x 16' storage shed with electricity. The shed is located in the front of the property and is directly on the water. A move-in ready home offering timeless charm and beautiful water views. Whether you're looking for a peaceful year-round residence or a relaxing waterfront retreat, this special property offers a rare chance to own at home where history and scenic beauty come together.

3287 Marsh Rd, Ewell

Listing courtesy of Wilson Realty. Contact:

20767 Abell Rd, Abell
$199,999
On nearly 3 acres this is a rare opportunity to own a buildable waterfront parcel in a secluded and peaceful setting. Located along a quiet one-way street with minimal traffic, this property offers privacy while still providing convenient access to surrounding amenities. The lot is currently wooded and level, offering an ideal canvas to bring your builder and custom home plans. The property has already been perc tested and approved by the health department for a mound septic system, helping streamline the building process. Opportunities like this are increasingly hard to find—secure your chance to own a truly special piece of waterfront land! Come see it today!

20767 Abell Rd, Abell

Listing courtesy of RE/MAX One. Contact:

32745 Hunt Ln, Galena
$725,000
3 Beds ⋅ 2 Baths
Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. Enjoy your private dock, boat lift, and plenty of space for kayaks, paddleboards, and other water toys. The home features three bedrooms plus a walkout basement ready for your vision—ideal for creating additional living space, a recreation area, or guest accommodations. With easy access to points north and located less than 10 minutes from Middletown, Delaware, this property is perfectly suited as a weekend getaway or a comfortable downsized waterfront retreat.

32745 Hunt Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

4721 Oak Rd, Shady Side
$998,000
4 Beds ⋅ 3 Baths
Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking panoramic views stretching all the way to the Bay Bridge. Meticulously maintained and truly move-in ready, this exceptional property combines luxury, comfort, and the best of coastal living. The main level features beautiful hardwood floors, a spacious gourmet kitchen with granite countertops, stainless steel appliances, and an open layout overlooking the inviting family room with a gas fireplace and spectacular Bay views. A main-level bedroom and full bath provide the perfect accommodations for guests. Upstairs, you'll find three additional bedrooms and two full baths, including a stunning waterfront primary suite. Wake up each morning to endless water views through walls of glass, then step onto your private covered terrace to enjoy your morning coffee while watching the sunrise over the Chesapeake Bay. Outside, your private pier offers the perfect place to fish, crab, or take the boat for a day on the water. Cruise to the many nearby waterfront restaurants and marinas, or simply relax and enjoy the peaceful waterfront setting. Conveniently located with an easy commute to Annapolis, Washington, D.C., and Baltimore, this remarkable home is nestled in the charming waterfront community of Felicity Cove. If you've been dreaming of exceptional Chesapeake Bay waterfront living, this is a home you won't want to miss.

4721 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

202 Muir St, Cambridge
$519,900
3 Beds ⋅ 4 Baths
Waterfront Living with a Deeded Boat Slip on Cambridge Creek - Enjoy beautiful water views, three screened porches and a deeded deep-water boat slip in this spacious three-level residence in the desirable Waterside community. Thoughtfully designed with approximately 3,000 square feet of living space (per floor plans) the home offers the comfort of a single-family home with the ease of low-maintenance living. The main level features an open floor plan with spacious living and dining areas, well-appointed kitchen with granite countertops, stainless steel appliances, island seating and abundant storage plus a large screened porch overlooking the water. The entry level offers a flexible family room with a full bath and screened porch, ideal for guests, a home office or recreation. Upstairs, the waterside primary suite features vaulted ceilings, large walk-in closet, spacious bath, private screened porch and an adjoining office or sitting area. Just blocks from downtown Cambridge's restaurants, shops, marina and waterfront parks, this exceptional home offers easy access to Cambridge Creek and the Choptank River. Square footage is based on floor plans. Tax records may differ and buyers should verify.

202 Muir St, Cambridge

Listing courtesy of TTR Sotheby's International Realty. Contact:

3197 Marsh Rd, Ewell
$215,000
2 Beds ⋅ 1 Baths
Be captivated by this two-bedroom, one-bathroom waterfront home nestled in the charming village of Rhodes Point on historic Smith Island, Maryland. This custom-built 2007 home has many outstanding features including a wraparound deck, outside shower, new kitchen cabinets, appliances, flooring. It only requires a few finishing touches, some trim, molding, and doors, to complete its look. Don’t miss out on this exclusive opportunity to tour this beautiful home with amazing views of the Chesapeake Bay! Call today to schedule your private showing.

3197 Marsh Rd, Ewell

Listing courtesy of Wilson Realty. Contact:

5120 Sea Fossil Dr, Huntingtown
$325,000
Year-round CHESAPEAKE BAY VIEWS highlight this beautiful, BUILDABLE 1.18-acre homesite in desirable Huntingtown! This is the last available lot in Bayview Manor Estates, a small, exclusive enclave of just 5 luxury custom homes with NO HOA, located on a scenic, level plateau overlooking the Bay. CLEARED and MOSTLY LEVEL, this lot offers an outstanding setting to build your dream custom home designed to maximize views of the Bay and the lovely natural surroundings. Tucked away near the end of a private, paved road, the protected wooded open space located directly across the street and wrapping around the end of the community enhance the scenery and assure that the peaceful, picturesque setting of this very special place will be preserved. ✨ Just as importantly, this property already has renewed PASSING PERC TESTS and a septic plat, saving valuable time and expense. An existing driveway is also in place which could potentially help reduce site development costs. ✨ Imagine relaxing on your future porch while LISTENING TO THE WAVES and watching the sun rise over the Chesapeake Bay, or entertaining family and friends as BOATS PASS IN THE DISTANCE, with the ever-changing Bay scenery providing a mesmerizing backdrop. ✨ Located in sought-after Northern Calvert County, you'll enjoy highly rated schools, scenic countryside, and convenient access to the Chesapeake Bay lifestyle, including the boardwalks, beaches, marinas, and waterfront dining in nearby North Beach and Chesapeake Beach. Annapolis, Joint Base Andrews, and Washington, D.C. are all within an easy commute.✨ If you've been looking for land, you know that it's become increasingly difficult, if not impossible, to find a large, buildable homesite with good, usable, level land and passing perc tests anywhere in Northern Calvert County, so to find one that has all of that AND year-round Chesapeake Bay views is a rare opportunity not to be missed! ✨ Don't miss out on your chance to own one of the BEST LOTS LEFT IN CALVERT COUNTY! Schedule a tour to walk the lot today! (Please note: Although there is NO HOA, there are covenants requiring that any home built in the community be at least 3000 sq. ft. )

5120 Sea Fossil Dr, Huntingtown

Listing courtesy of Redfin Corp. Contact:

2503 Legacy Ct, Cambridge
$899,999
4 Beds ⋅ 3 Baths
Cambridge - waterfront paradise on Jenkins Creek, offering direct, easy access to the Choptank River! Nestled on a private lot with a peaceful, country feel, this charming home combines serene Eastern Shore living with the convenience of being just minutes from downtown Cambridge. Step inside to bright, sunlit interiors featuring soaring cathedral ceilings and rich hardwood floors. Cozy up on cool winter evenings by the fireplace/ woodstove, or unwind in the spacious main-floor primary suite, complete with a walk-in closet, updated bath with a walk-in shower, and direct access to the deck through large sliding doors framing picturesque water views. Upstairs, you'll find two additional bedrooms, a full bath, a versatile bonus room or potential fourth bedroom, and generous extra space ideal for storage or future expansion. Outdoor living is truly exceptional, featuring two private decks, a welcoming front porch, and a wonderful screened porch perfect for relaxing or entertaining. The rip-rapped shoreline includes a private dock equipped with water and electricity—ready for your boating and fishing adventures. Complete with an attached oversized garage, this captivating coastal retreat has so much to love!

2503 Legacy Ct, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact:

1648 Taylors Island Rd, Woolford
$849,900
3 Beds ⋅ 2 Baths
Imagine waking up to sweeping waterfront views, launching your kayak from your private beach, and ending the day with uninterrupted sunset skies right from your own yard! This stunning, completely remodeled coastal retreat combines peace of mind with exceptional investment potential. Featuring a new roof and new HVAC system, every detail of this home has been thoughtfully updated, including fresh LVP flooring throughout with all-new subflooring and beautifully updated bathrooms. The gourmet kitchen boasts sleek granite countertops, perfect for entertaining family and guests. Step outside to enjoy direct waterfront living with a riprapped shoreline and your very own private beach access—ideal for launching kayaks, soaking up sunset views, or enjoying water recreation. Detached garage. Currently operating as an active Airbnb with a proven rental history, this property is ready to generate income from Day 1. Furnishings are negotiable, offering a seamless, plug-and-play opportunity for vacation home buyers or investors alike.

1648 Taylors Island Rd, Woolford

Listing courtesy of Coldwell Banker Realty. Contact:

1619 Perseus Rd, Cambridge
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to Crump Point, an extraordinary renovated waterfront sanctuary nestled on approximately 5± private acres overlooking the tranquil waters of Church Creek. Offering exceptional privacy and captivating panoramic views, this remarkable property captures the essence of Eastern Shore waterfront living. Thoughtfully designed to embrace its breathtaking surroundings, the 3-bedroom, 2.5-bath residence offers stunning water views from nearly every room. The main level is anchored by a spacious gourmet kitchen featuring an oversized island, creating the perfect space for entertaining or gathering with family while enjoying the picturesque waterfront backdrop. All new stainless steel appliances throughout. The first-floor primary suite provides a private retreat complete with serene waters views, waterside deck, walk-in closet, walk-in shower, and oval soaking tub. Outdoor living is equally impressive with a spacious waterfront deck, screened waterside porch, and an upper-level waterside deck—ideal for morning coffee, evening sunsets, or simply taking in the ever-changing beauty of Church Creek. A private pier offers direct access to the water for boating, kayaking, fishing, and crabbing, while the beautifully landscaped grounds provide ample room to enjoy the peaceful surroundings. Additional features include a circular driveway, attached two-car garage, first-floor split-unit heating and cooling, and second-floor central air with baseboard heat. Whether you’re seeking a full-time residence or a weekend waterfront escape, Crump Point offers a rare opportunity to own an exceptional Eastern Shore property where privacy, natural beauty, and timeless waterfront living come together in perfect harmony.

1619 Perseus Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

565 Glendale Rd Unit 213, Oakland
$215,000
1 Beds ⋅ 1 Baths
Turnkey lakeview studio at The Suites at Silver Tree! This condo has an average annual gross rental of $25,342. Enjoy beautiful views of Deep Creek Lake from your private covered balcony while owning one of the area's most desirable vacation destinations. This fully furnished studio offers an open floor plan with a king bed, sleeper sofa, cozy gas fireplace, kitchenette, dining area, and full bath, making it the perfect weekend getaway or investment opportunity. The Suites at Silver Tree features an impressive timber-frame lobby with soaring ceilings and massive stone fireplaces, an expansive lakeside deck, sandy beach, lake access, on-site marina, fitness center, sauna, game room, and Dutch's at Silver Tree restaurant. Ideally located in the heart of Deep Creek Lake, you're just minutes from Wisp Resort, golf, hiking, shopping, and year-round recreation. Whether you're looking for a low-maintenance vacation home, rental property, or your own place at the lake, this one checks all the boxes. Call today for your private showing!

565 Glendale Rd Unit 213, Oakland

Listing courtesy of The KW Collective. Contact:

31720 Ayres Dr, Trappe
$1,500,000
4 Beds ⋅ 3 Baths
A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact:

11395 Hayman Dr, Princess Anne
$449,900
4 Beds ⋅ 3 Baths
Welcome to waterfront living on the beautiful Manokin River! This spacious 4 bedroom, 2.5 bath home is perfectly situated on .82 acres offering the ideal blend of privacy and convenience with NO HOA. Designed to embrace its stunning waterfront setting, the home features a spacious bedrooms, an expansive wraparound screened porch, composite decking, a cozy gas outdoor fireplace, an attached garage and a shed with electricity (conveys as it). Enjoy the convenience of public water and sewer while being just minutes from downtown. Waterfront opportunities like this are rare - schedule your private tour today!

11395 Hayman Dr, Princess Anne

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

803 Seabreeze Rd, Cambridge
$799,900
4 Beds ⋅ 3 Baths
Experience the natural beauty and tranquility of Maryland's Eastern Shore from this exceptional waterfront retreat in Dorchester County. Tucked away at the end of a private street on Brooks Creek, this remarkable property boasts over 180 degrees of breathtaking water views from its spectacular lot. Designed for boating enthusiasts, the waterfront features approximately 120 feet of pier with multiple boat lifts, a bulk headed shoreline, a private boat ramp, a small sandy beach, and expansive lawn surrounded by mature landscaping. This charming 4-bedroom, 3-bath home has been thoughtfully designed to capture panoramic water views from virtually every room. The updated kitchen features granite countertops, stainless steel appliances, and ample workspace, while hardwood flooring flows throughout the main living areas. The open floor plan seamlessly connects the spacious dining area and living room, creating an inviting setting for everyday living and entertaining. Three generously sized bedrooms are located on the main level. The impressive family room is the heart of the home, showcasing a gas fireplace, built-in bar, and walls of windows that frame the ever-changing waterfront scenery. Upstairs, the private primary suite is a true sanctuary, featuring soaring cathedral ceilings and dramatic floor-to-ceiling windows that provide sweeping panoramic water views from both the sleeping and sitting areas. A second gas fireplace creates a cozy atmosphere, while the luxurious en-suite bath offers a garden tub, walk-in shower, and spacious walk-in closet. Outdoor living is equally exceptional. Relax on the expansive screened porch while enjoying spectacular sunsets and the abundant wildlife and waterfowl that call Brooks Creek home. An oversized concrete patio provides additional space for entertaining, and two storage sheds—including one equipped with two refrigerators—offer excellent convenience for boating, fishing, and gatherings. Dual driveways provide ample parking for multiple vehicles, boats, and trailers. From your private pier, enjoy easy access by boat to Tilghman Island, St. Michaels, and many of the Mid-Shore's most charming waterfront towns, where you'll find renowned restaurants, marinas, boutique shopping, and endless opportunities to experience the best of Eastern Shore living. Whether you're seeking a full-time residence, weekend escape, or the ultimate waterfront lifestyle, this rare Brooks Creek property offers an extraordinary combination of privacy, recreation, and unforgettable views.

803 Seabreeze Rd, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

1979 Baltimore Annapolis Blvd, Annapolis
$3,000,000
5 Beds ⋅ 2 Baths
A truly extraordinary opportunity awaits in one of Annapolis' most coveted waterfront locations. Situated in the historic Ferry Farms neighborhood, 1979 Baltimore Annapolis Boulevard is one of only thirteen homes positioned directly across the Severn River from the U.S. Naval Academy, offering uninterrupted panoramic views that have captivated generations. Imagine enjoying the Blue Angels soaring overhead each May from your own front lawn or dock—an experience few will ever call home. Rich in architectural character, the residence showcases the craftsmanship and charm of its era, including original hardwood floors, a classic wood-burning fireplace, vintage kitchen, inviting sunroom, screened porch, and period details that create a warm sense of history. The home's generous square footage spans three levels, blending the original residence with a substantial 2015 addition that expanded both its living space and functionality while preserving its unique personality. For buyers with vision, this property presents an exceptional opportunity to create a landmark waterfront residence tailored to today's lifestyle. Architectural renderings, renovation plans, a professional landscape design, and contractor cost estimates are available to help bring that vision to life, allowing the next owner to build upon an already remarkable foundation. The original home includes a main-level bedroom and full bath, while the upper level offers four additional bedrooms, including a primary suite with a private balcony overlooking the water. The 2015 addition introduced a spacious three-car garage, an expansive loft, and an additional bedroom perfect for guests, a home office, or a studio. A future bathroom has already been considered, with a rough-in located beneath the connecting section of the second floor. The lower level offers even more possibilities, featuring a second wood-burning fireplace, laundry area, utility space, and an impressive workshop with soaring ceilings and direct access to the garage and backyard—ideal for craftspeople, hobbyists, or future finished living space. Outside, the waterfront amenities are equally compelling. The private deep-water pier and bulkhead, completed in 2003, feature approximately 10 feet of water depth, a 40,000-pound boat lift, a 15,000-pound lift, and two 1,500-pound personal watercraft lifts, making this an outstanding property for serious boaters. A built-in outdoor barbecue and expansive waterfront setting invite effortless entertaining and relaxed evenings watching sailboats drift past the Academy. Properties of this caliber, location, and potential rarely become available. Whether thoughtfully restoring its historic character, executing the available renovation plans, or creating a legacy waterfront estate of your own design, this is a once-in-a-generation opportunity to own an irreplaceable piece of Annapolis waterfront in one of its most prestigious and tightly held neighborhoods.

1979 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

16173 Cobb Island Rd, Newburg
$380,495
3 Beds ⋅ 1 Baths
Exceptional Waterfront Opportunity – Bring Your Vision This level waterfront property offers a rare opportunity for an investor, builder, or buyer looking to create a custom waterfront retreat. The home is not safe to enter and is being sold as-is. Interior access will not be permitted due to ongoing renovations and safety concerns. Most windows have been removed and securely boarded. The current owner has already completed substantial improvements, providing a strong foundation for the next phase of the project, including: New metal roofs on both the house and outbuilding Removal of eight approximately 100-foot dead trees Interior demolition completed, including removal of drywall and bathroom fixtures Underground electrical service installed New concrete back porch Masonry fireplace remodeled New well pump installed Large interior water pressure tank installed and currently supplying water New vinyl boundary fence installed by Long Fence Shed interior freshly painted Professional termite treatment completed The waterfront lot is level and offers excellent potential. The existing pier will require rebuilding, creating the opportunity to design a dock that meets your needs and applicable permitting requirements. If you've been searching for a waterfront property where much of the difficult preparation work has already been completed, this is an opportunity you won't want to miss. Bring your contractor, your imagination, and your plans to transform this property into something truly special.

16173 Cobb Island Rd, Newburg

Listing courtesy of O'Brien Realty ERA Powered. Contact:

21610 Hidden Creek Dr, Rock Hall
$699,000
4 Beds ⋅ 3 Baths
Enjoy a long, secluded driveway to a 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Grey’s Inn Creek. The home features vaulted ceilings and has access to a private pier and dock; it’s perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this property is being sold As-Is, offering a chance to remodel and complete your vision. Current owners originally built the house in 1986 as a cabin with a later add-on to the original structure. Rock Hall is a waterfront town located directly on the National Chesapeake Scenic Byway in Kent County. The boat pier will need extensive work and is non-operational. Property is being sold AS-IS with a Right-to-Inspect. Tremendous opportunity for a wooded, waterfront residence with some sweat equity.

21610 Hidden Creek Dr, Rock Hall

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

9054 Kingfisher Ct, Hebron
$134,900
2 Beds ⋅ 2 Baths
*RECENT PRICE ADJUSTMENT* - Nestled in the serene community of Hebron Woods, this charming manufactured home offers a perfect blend of comfort and functionality. Built in 1995, this well-maintained single-wide home boasts a spacious layout with 2 bedrooms and 2 full bathrooms, making it an ideal retreat for those seeking a peaceful lifestyle. Step inside to discover an inviting open floor plan that seamlessly connects the kitchen and dining area, perfect for entertaining or enjoying quiet meals at home. The kitchen features a convenient island, providing additional prep space and a cozy spot for casual dining. The family room, located just off the kitchen, is enhanced by a warm brick wood burning fireplace, creating a welcoming atmosphere for gatherings or relaxing evenings. The primary suite is a true sanctuary, complete with a walk-in closet and a private bathroom featuring a soaking tub and a stall shower. Additional interior highlights include plush carpeting, a ceiling fan for added comfort, and vinyl flooring that adds durability and style. Outside, the property is equally enchanting. Enjoy the tranquility of your own pond view from the deck, where you can unwind with a morning coffee or host evening barbecues. The lot is situated on a peaceful cul-de-sac, providing a sense of privacy and community. An included shed offers ample storage for outdoor equipment or hobbies, ensuring your space remains organized and clutter-free. With off-street parking for two vehicles, convenience is at your fingertips. The home is also located near a picturesque pond, perfect for those who appreciate nature and outdoor activities. Whether you enjoy fishing or simply taking in the views, this property offers a unique water-oriented lifestyle. This home is not just a place to live; it's a place to create lasting memories. With its inviting interior, charming exterior, and beautiful surroundings, it's ready to welcome you home. Don't miss the opportunity to make this delightful property your own! Call today for your private showing or check out the 360-degree virtual tour!

9054 Kingfisher Ct, Hebron

Listing courtesy of Coldwell Banker Realty. Contact:

14 Stilwater Dr, Swanton
$3,299,900
8 Beds ⋅ 9 Baths
Luxury Lakefront wth a Dock Slip at Deep Creek Lake - Experience refined lake living at 14 Stillwater Drive, an exceptional modern home in the desirable Stillwater Community offering luxury, comfort, and spectacular lake views. On nearly 3/4 acres of lakefront mountain pasture, this 8-bed, 8.5 Bath boasts almost 9000 sq ft of finished living space. Inside, soaring ceilings and expansive windows fill the home with natural light, while a dramatic floor-to-ceiling stone fireplace creates a striking focal point in the main living area. The spacious open floor plan is ideal for both everyday living and entertaining, with a well-appointed gourmet kitchen, flowing seamlessly into the dining and great room. Indoor pool for year-round enjoyment. The lower level features a sprawling rec room with multiple game tables, wet-bar, and private theater room. 6 en suites with two overlooking the lake from their private balconies. Outside is the beautiful lakeside patio, the perfect place to relax, entertain, soak in the hot tub, or take in the peaceful surroundings and panoramic water views and abundant wildlife, including deer, beavers, turtles, geese, and eagles! Self-sufficient with a whole-house generator, several zoned HVAC system, and full water treatment complete with UV light. With the recently added sprinkler system, "Castle on the Cove" is rent-ready and sure to become one of Deep Creek Lake's premier vacation rentals. Combining timeless craftsmanship, resort-style amenities, and an unbeatable setting, this one-of-a-kind home offers an exceptional lifestyle inside and out. Don’t miss your chance to see this remarkable Deep Creek classic… Call today to schedule your private showing!

14 Stilwater Dr, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

2235 State Park, Swanton
$2,100,000
6 Beds ⋅ 4 Baths
Every once in a while, a truly special property comes to market—and this is one of them. Perfectly positioned along the shores of Deep Creek Lake, this 6-bedroom, 4-bath lakefront home offers the rare combination of spectacular waterfront, privacy, and an unbeatable location. With an incredible 268 feet of gently slopping lake frontage, a private Type A dock, and coveted western exposure, you'll enjoy breathtaking sunsets. Whether you're boating, swimming, paddleboarding, or simply relaxing by the water, this property is designed to embrace the Deep Creek lifestyle. Just minutes away, Deep Creek Lake State Park offers miles of hiking and biking trails, a sandy beach, and year-round outdoor recreation. Currently operating as the vacation rental "Our Golden Retreat," it provides the opportunity to enjoy the home while generating rental income. Properties with this much lake frontage, western sunset views, a private dock, and a premier State Park Road location rarely become available. If you've been waiting for the perfect Deep Creek Lake getaway, your search ends here.

2235 State Park, Swanton

Listing courtesy of Railey Realty, Inc.. Contact:

12903 Windy Dr, Ocean City
$9,500,000
6 Beds ⋅ 5 Baths
This 37-acre Waterfront Estate in the desirable West Ocean City Community of Captains Hill stands among Worcester County’s true legacy properties. A rare combination of Coastal Luxury, privacy, acreage and future opportunity. Set on a expansive rise overlooking the bay, the Estate commands sweeping water and skyline views that shift elegantly from sunrise to the golden glow of sunset. A long driveway leads you to the 8000+ Sq Ft Coastal Residence, a grand yet serene retreat surrounded by park-like grounds and mature landscape that creates an atmosphere of total privacy. The main Estate and grounds encompass 27 acres that feature a diverse landscape designed for both beauty and functionality. Such highlights include a 3-acre freshwater pond that anchors the properties tranquil setting, an outdoor pool with surrounding deck ideal for families and entertaining, an expansive lawn for gatherings and pets, a large covered porch perfect for enjoying the broad water views and nature, covered parking entrance and a three-car garage. The residence itself offers the architectural presence and scale expected of a Coastal Estate of this magnitude, with generous living spaces, impressive ceiling heights and endless potential for customization or enhancement. In addition, this Estate offers additional parcels and development potential that allows for flexibility for future use. Included in the offering is a 2.73-acre Waterfront Lot and 20 plated lots with their own road frontage. This rare land portfolio provides exceptional opportunities, ideal for a private compound, multi-generational retreat, curated development or long-term investment that makes this property uniquely valuable. Opportunities of this size, location and versatility rarely ever come to market. With commanding views, coastal proximity, and expansive acreage, this Captain’s Hill Estate stands as one of the region’s premier offerings, a property with both present-day grandeur and limitless future potential. A Coastal Treasure without equal.

12903 Windy Dr, Ocean City

Listing courtesy of Holiday Real Estate. Contact:

20401 Nanticoke Dr, Nanticoke
$850,000
4 Beds ⋅ 3 Baths
Welcome to 20401 Nanticoke Dr!!! This stunning waterfront home has been completely redesigned by the the Acclaimed Savannah Jameson Studio of Washington DC!!! Setting Directly at the mouth of the Nanticoke River and overlooking the Tangier Sound/Chesapeake Bay, this One of a Kind Gem boast some of the most breathtaking Sunsets this region has to offer. The home has been completely renovated starting with the Engineered Hardwood Flooring, Gourmet Kitchen complete with Large Island and Massive Pantry. The Gas Stove and Built In Refrigerator with Custom Cabinetry add to the Overall feeling of Excellence in the Home. The Open Floor Plan makes the main floor living great for entertaining, while the existing Fireplace creates a cozy feel to the space!!! The entire Downstairs living area shares Panoramic views of the Water or take a closer look from the Open Deck area as you let the Bay Breeze and the scent of the saltwater take you to a place of calm and relaxation. The Owners Suite has it's own amazing views and the en suite and Walk in Closet give you a large private area for privacy! Completing the main floor are two additional bedrooms, a full bath, and ample laundry area for your convenience. The Second Floor features a Huge Open Room great for a Second Living Space or a Recreational Area for the youngsters! A Fourth Bedroom and Third Full Bath complete this thoughtful layout that makes large gatherings a breeze!!! Walk out onto the recently renovated Pier to cast a line and land a Striped Bass or drop some crab pots and catch some delicious Blue Crabs or maybe just take in the exquisite backdrop this property provides. The exterior of the Home has had as much care as the interior. It has been lifted above the flood plain, features new exterior siding and a new roof. Whether you're searching for a forever home, weekend retreat or an absolute rental machine... look no further!!! Schedule your private tour TODAY!!!

20401 Nanticoke Dr, Nanticoke

Listing courtesy of RE/MAX Advantage Realty. Contact:

7349 Mary Dr, Port Tobacco
$535,000
4 Beds ⋅ 3 Baths
This uniquely inviting, superbly maintained home sits on .84 private acreage bordering on 200 feet of navigable Port Tobacco River frontage. Owned throughout its history by one family, this well cared for and stately, all-brick, 2,442 square foot Home features 4 bedrooms, 2.5 fully renovated bathrooms, formal dining room, separate living room and sun-filled family room w/ fireplace located just off the modern kitchen w/ granite counters, high-end cabinetry and breakfast-for-two seating with your own exclusive view of the river. Additional features include hardwood floors throughout the majority of the home with ceramic tile and newly installed LVP making up the rest. The primary bedroom boasts a spacious walk-in closet and direct access to private deck overlooking the backyard and its festive 16’ octagonal gazebo, fire pit, mature trees, Of particular significance is the Home’s ultra efficient, energy-independent profile. Thanks to the 15.91 kW Solar System (OWNED) and integrated energy-saving features, including but not limited to a high efficiency HVAC system and tankless/on-demand water heater (both electric), the cost for electricity is consistently ZERO DOLLARS (potentially income producing). Furthermore, the home has been upgraded to a 350-amp electrical service, perfect for EV charging, a hot tub, fully-equipped work shop and more. Additional items of interest include two 14-ft tandem kayaks with built-in storage racks, front porch chair swings,, active chicken coop , private parking for 10+ vehicles, full-sized freezer, 12' x 28' workshop/storage building, separate 4' x 8' shed, rain water collection barrels, shaded riverside pergola and so much more. Well-priced and move-in ready. Hope to see you soon.

7349 Mary Dr, Port Tobacco

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

44908 Hickory Landing Way, Hollywood
$799,000
5 Beds ⋅ 3 Baths
17.5 Acres on Cuckold Creek. Rare large waterfront property of 17.5+ acres to provide you peace, quiet and privacy on highly desired Cuckold Creek. The 17.5 acres are mostly level and heavily wooded with walnut, Cypress, Maple, Oak and pine . Wildlife abounds. The Hickory Landing community dock on the property will have your own boat slip. A large garden plot is right on Hickory Landing Way, but tucked way down a beautiful long and winding driveway, you find the house on the water. Originally built in 1983, the house takes full advantage of the extraordinary water view of Cuckold creek with soaring cathedral ceilings of exposed beams and 2"x4" tongue and groove. The addition from mid 90's also takes full advantage of the extraordinary water views with dozens of Anderson window casement windows in excellent condition. The property contains a solid one room cabin with wood stove for you to use your imagination with. New standing seam metal roof put on the cabin in 2022. New 10'x14' outbuilding with 8'doors placed on the property this summer. Property sold as-is, however numerous improvements made this year, You could be waiting a very long time before another property like this comes to market. Please call listing agent for more information.

44908 Hickory Landing Way, Hollywood

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

117 Ne Isle Dr, North East
$315,000
2 Beds ⋅ 2 Baths
Back on the market, no fault of sellers. Welcome to 117 NE Isle Drive, a beautifully upgraded waterfront-community condominium in the sought-after North East Isles, located at the head of the Chesapeake Bay. From the moment you step inside this lower-level unit, you'll appreciate the rich Brazilian hardwood floors, elegant granite finishes, and premium stainless steel appliances. The main level features an open-concept living, dining, and kitchen area designed for comfortable everyday living and effortless entertaining. A versatile office/guest bedroom showcases stunning custom built-ins, a granite desk, and a convenient Murphy bed, making it ideal for working from home or accommodating visitors. The gourmet kitchen is equipped with stainless steel appliances, a cooktop, trash compactor, and gorgeous granite countertops. The living room opens to a private deck with seasonal views of the North East River, creating the perfect setting for morning coffee or evening relaxation. The lower level offers a spacious owner's suite complete with a walk-in closet, luxurious bath featuring a walk-in shower and jetted soaking tub, and direct access to a second private deck. Additional lower-level spaces include a laundry area and a flexible bonus room ideal for a home gym, den, or hobby room. This exceptional home is loaded with upgrades and provides access to outstanding community amenities, including a swimming pool, tennis and pickleball courts, boat launch, boat storage, picnic area, and fire pit. Residents also have opportunities to purchase or lease slips in the private community marina. Located in the charming town of North East, Maryland, you'll enjoy easy access to local restaurants, boutiques, marinas, state parks, and year-round waterfront activities. Conveniently situated less than an hour from Baltimore, Philadelphia, and Lancaster, this property offers the perfect blend of small-town charm and regional accessibility. Experience the best of Chesapeake Bay living at North East Isles.

117 Ne Isle Dr, North East

Listing courtesy of Integrity Real Estate. Contact:

1704 Twickenham Rd, Pasadena
$395,000
3 Beds ⋅ 2 Baths
Rare Waterfront Opportunity on Cornfield Creek — Bring Your Dreams, Build Your Vision Welcome to 1704 Twickenham Rd, a hidden gem tucked in Pasadena's sought-after Lake Shore community with 25 feet of private waterfront on Cornfield Creek. This .19-acre lot offers direct water access just minutes from the Magothy River and Chesapeake Bay. This is a true ground-up opportunity: the house has been fully gutted down to the studs — currently no bathrooms or bedrooms remain — and the property will need a complete rebuild, including a new well and pier. Plans have already been submitted for approval for a brand-new 4 bedroom, 2.5 bath, 3-level home, putting you steps closer to breaking ground on the waterfront retreat you've always imagined. Set on a quiet street close to schools, shopping, and commuter routes, with no HOA to slow you down. Whether you follow the submitted plans or bring your own vision, this is your chance to build exactly what you want, from the ground up. Don't just buy a house on the water. Build your dream home on it. Set on a quiet street close to schools, shopping, and commuter routes, with no HOA to slow you down. Whether you follow the submitted plans or bring your own vision, the groundwork is done — all that's left is to build. Don't just buy a house on the water. Build your dream home on it.

1704 Twickenham Rd, Pasadena

Listing courtesy of Keller Williams Flagship. Contact:

6150 Oxford Rd, Easton
$6,375,000
2 Beds ⋅ 3 Baths
Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

6150 Oxford Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

7429 Bay Front Rd, Sparrows Point
$1,799,000
5 Beds ⋅ 5 Baths
Imagine ending each day with the sun setting over the water, your boat just steps away, while gathered on a covered porch where every detail was designed for effortless living. This custom waterfront estate isn't simply a home, it's the backdrop for a lifetime of unforgettable moments. Built with intention and positioned on 1.26 elevated and beautifully landscaped acres secured by a private electronic gate, this one of a kind home offers a true coastal lifestyle. Expansive windows, soaring 10-foot ceilings, and an open floor plan capture breathtaking water views throughout. At the heart of the home, the chef's kitchen features a gourmet island with breakfast bar, premium appliances including Breville convection microwave grill combo, KitchenAid microwave/oven, oversized refrigerator, double ovens, lighted cabinetry, and a walk-in pantry. Through double sliding doors you’ll discover a covered composite deck complete with vaulted ceilings, a fan for a never ending breeze, retractable screens, propane fireplace, television, and grilling station where you’ll enjoy sweeping views of the waterfront. Sip your coffee while you watch the eagles, osprey and great blue herons soar by. This is truly where you’ll enjoy seamless indoor/outdoor living. Outside, your private resort awaits. Relax beside the 18' x 36' inground pool with custom Eagle Ray mosaics, built in benches and diving board, or head to the 120-foot private pier with picnic area,10,000 lb boat lift, and dual jet ski lifts for an evening on the Chesapeake. Designed for entertaining and everyday comfort, this spectacular home offers 5-6 bedrooms, 4.5 baths, a private office, loft/library, elevator servicing every level, and a finished lower level ideal for guests, recreation room or multi-generational living. The waterfront primary suite provides panoramic views, dual walk-in closets, and a spa-inspired bath with a soaking tub overlooking the shoreline. Exceptional craftsmanship includes 2x6 construction, 2-inch closed-cell spray foam insulation, floors and walls insulated for sound, dual-zone HVAC, central vacuum, an oversized climate-controlled garage capable of parking full size SUV or trucks. A sturdy 10x16 shed provides additional outdoor storage. At more than 20 ft above sea level, no flood insurance is required. Enjoy your bay front lifestyle without the worry. Built in 2021, offering timeless quality, unmatched waterfront amenities, and future subdivision potential, this is a rare opportunity to own a home where every detail was thoughtfully designed, and every day feels like a vacation. Located on a quiet street in a well-established neighborhood that is rich with local history, near 1300 acre North Point State Park and Fort Howard Park, you’ll feel worlds away while staying close to Baltimore, Annapolis, and DC. Boaters will appreciate easy access to top destinations on the Bay. Some homes are simply built. Others are thoughtfully crafted to become the place where life's best memories unfold. This is one of them. Schedule your private tour and experience what makes this extraordinary property unlike anything else on the market.

7429 Bay Front Rd, Sparrows Point

Listing courtesy of Cummings & Co. Realtors. Contact:

34082 Market St, Pocomoke
$199,500
Waterfront commercial property along the Pocomoke River! Great road exposure on Market St into downtown Pocomoke. 1,100 sq ft building built in 1940 with lots of original charm and character. Front of building has new subflooring. Over 2.5 acres with 215' of water frontage give you loads of potential of what this property could be. Beautiful views of the draw bridge and Cypress Park. Close to restaurants, shops, and public amenities. Property cannot be used as a food service facility. Owner financing is available.

34082 Market St, Pocomoke

Listing courtesy of The Land Group. Contact:

34082 Market St, Pocomoke
$199,500
Waterfront commercial property along the Pocomoke River! Great road exposure on Market St into downtown Pocomoke. 1,100 sq ft building built in 1940 with lots of original charm and character. Front of building has new subflooring. Over 2.5 acres with 215' of water frontage give you loads of potential of what this property could be. Beautiful views of the draw bridge and Cypress Park. Close to restaurants, shops, and public amenities. Property cannot be used as a food service facility. Owner financing is available.

34082 Market St, Pocomoke

Listing courtesy of The Land Group. Contact:

1069 Shore Acres Rd, Arnold
$1,650,000
5 Beds ⋅ 4 Baths
Waterfront on two sides—that's the rare gift waiting at 1069 Shore Acres Rd, where a flat, sun-drenched parcel meets the water along its front and southern edge, just steps from a secluded community beach. This 4-bedroom, 2.5-bath home offers 2,386 square feet of coastal living in one of Arnold's most coveted enclaves. Recent investments make this residence as sound as it is scenic. A cascade of 2022 upgrades—new roof, siding, windows, front door, deck, and a redesigned porch overhang—refreshed the exterior top to bottom. Crawl space waterproofing (2021), a reconditioned iron balcony with spiral stairs (2023), plus a 2025 bulkhead along the riverfront and side and a newly parged foundation give buyers genuine peace of mind. Tucked at the rear sits a detached one-car garage with workshop, ideal for hobbyists and boaters alike. Climb the separate staircase to discover a fully finished second-level retreat, complete with living quarters and a luxurious bath—perfect for guests, extended family, or a private studio escape. From the garage living area, you can look across Lake Placid (the one in Arnold) and out to the Magothy throughout every season. Life in Shore Acres means embracing the rhythm of the water, with quiet mornings on the deck and easy access to the neighborhood beach. When you crave something livelier, downtown Annapolis beckons with fine dining, boutique shopping, and historic charm just minutes away. Route 50 keeps Baltimore and Washington, D.C. comfortably within reach. Homes offering this blend of dual waterfront exposure, modern updates, and flexible living space rarely surface. Come experience it firsthand.

1069 Shore Acres Rd, Arnold

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

100 Pier, Oxford
$1,095,000
3 Beds ⋅ 3 Baths
Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

6 Spa Creek Lndg Unit B2, Annapolis
$674,000
2 Beds ⋅ 2 Baths
Enjoy show-stopping sunsets and fabulous waterfront views of Spa Creek from this stunning condominium in the highly sought-after Shearwater complex in Eastport. This contemporary 2 bedroom condo is located on the second floor of building 6. From your private balcony, witness herons, egrets, ducks, and even the bald eagle in this bird and nature watchers’ paradise. Your view will feature a green valley that ends at the lagoon that leads directly to Spa Creek. In December, celebrate the famous EYC annual Parade of Lights in style by your wood-burning fireplace and in Spring/Summer enjoy the easy breeze with family and friends . The private community marina just steps away from your home, is the perfect place to dock your boat and store your kayak . It offers seamless access to Spa Creek, the Chesapeake Bay and beyond. Your luxury lifestyle also includes the choice to relax poolside, play tennis/pickleball on the courts, walk to town or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis waterfront dream has come true!

6 Spa Creek Lndg Unit B2, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

16101 Piney Point Rd, Piney Point
$549,900
3 Beds ⋅ 1 Baths
NEW PRICE! Some properties are purchased for the house. Others are purchased for the place. Set on a narrow finger of land between two bodies of water, 16101 Piney Point Road offers an extraordinary waterfront setting with sunrise light on one side and spectacular sunset views on the other. The existing cottage provides an immediate place to enjoy life, watch the sky change, enjoy the water, and begin imagining what might come next. Inside, the home is modest, comfortable, and full of personality, with water visible from several rooms, a spacious primary bedroom, two additional bedrooms, an updated full bath, central heating and air conditioning, laundry, and a simple kitchen with cooktop. Enjoy the property as your full-time residence or weekend retreat and explore the potential for future expansion designed to take fuller advantage of the remarkable setting and views, and over 492 linear feet of shoreline! Any future construction, expansion, elevation, or redevelopment is subject to governmental approvals and buyer verification. The neighboring property at 16104 Piney Point Road is also separately offered for sale, creating the rare possibility of acquiring a larger portion of the residential tip of Piney Point Road for a private family estate or multi-generational waterfront retreat. Each property is separately owned, listed, and offered for sale. ***PUBLIC SEWER ALREADY INSTALLED***

16101 Piney Point Rd, Piney Point

Listing courtesy of RE/MAX One. Contact:

3925 Shamrock Ct, Port Republic
$825,000
4 Beds ⋅ 3 Baths
Experience the best of waterfront living in this beautifully maintained split-foyer home situated on 1.15 private acres in a desirable waterfront community. Offering 4 bedrooms and 3 full baths, this property is the perfect blend of comfort, recreation, and relaxation. Currently enjoyed as a second home, it also offers excellent potential as a vacation retreat or short-term rental opportunity (buyer to verify local regulations). The bright, inviting main level is filled with natural light, while the finished lower level features a cozy propane fireplace, creating the perfect gathering space for family and friends. Additional highlights include a dedicated laundry room, water filtration system, abundant storage, an oversized two-car garage with attic storage, and an additional attic in the home. Step outside to your own private waterfront oasis featuring an in-ground gunite pool with a Loop-Loc safety cover, 184 feet of shoreline on scenic Battle Creek, and a private pier with boat lift. With approximately 4 feet of water at mean low tide, you'll enjoy easy boating access from your backyard. Battle Creek flows directly into the Patuxent River and onward to the Chesapeake Bay, providing endless opportunities for cruising, fishing, kayaking, paddleboarding, and waterfront adventures. Battle Creek is also one of the few waterways in the area that allows a wake zone, making it ideal for water skiing, tubing, and other water sports. Waterfront restaurants are just a short boat ride away, making every day feel like a vacation. The community's new pier, currently being completed in 2026 with new pilings, stringers, and decking, provides another wonderful amenity for residents to enjoy. A new roof installed in 2024 offers added peace of mind. Conveniently located just minutes from Solomons Island, you'll have easy access to charming waterfront restaurants, boutique shopping, marinas, seasonal events, museums, concerts, and the Annmarie Sculpture Garden & Arts Center. Whether you're looking for a year-round residence, a weekend escape, or an investment property with exceptional waterfront appeal, this home offers the lifestyle you've been dreaming of in one of Southern Maryland's premier boating communities.

3925 Shamrock Ct, Port Republic

Listing courtesy of RE/MAX One. Contact:

13202 Stone Harbor Ln Unit 106, Ocean City
$999,500
4 Beds ⋅ 4 Baths
Experience luxury coastal living in this spacious 4-bedroom townhome located in the prestigious gated community of Stone Harbor. This beautifully appointed residence includes a deeded boat slip on the community pier, offering effortless access to the water for boating enthusiasts. Designed to embrace its waterfront setting, the home features multiple outdoor living spaces where you can relax, entertain, and enjoy stunning water views. Whether you're seeking a year-round residence or an exceptional vacation retreat, this home offers the perfect blend of elegance, comfort, and an unparalleled waterfront lifestyle. Professional photos coming this week !

13202 Stone Harbor Ln Unit 106, Ocean City

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

1486 Downham Market, Annapolis
$2,999,900
5 Beds ⋅ 5 Baths
Seller financing available — an exceptional opportunity to own a distinguished Annapolis waterfront estate. Beautifully situated on 1.86 private acres in the prestigious Downs on the Severn, 1486 Downham Market offers a rare combination of protected deep water, gracious living and the extraordinary pleasures of life along the Severn River. With captivating water views, an impressive private pier and more than 5,200 square feet of beautifully appointed living space, this exceptional property offers a lifestyle to be enjoyed for generations. For the discerning boating enthusiast, the waterfront is truly remarkable. Positioned at the mouth of Clements Creek, a naturally protected harbor, the property features an impressive 180-foot private pier with three slips, 50-amp shore power, reinforced pilings ready for lifts, full riparian rights and approximately 11 feet of mean low water. Whether enjoying an afternoon on the Chesapeake Bay, an evening cruise along the Severn or the simple pleasure of having your yacht just steps from home, this setting is nothing short of extraordinary. Inside, walls of glass frame beautiful water views and fill the residence with natural light. Soaring ceilings, rich hardwood floors, elegant finishes and a striking two-sided stone fireplace create an atmosphere of warmth and sophistication. The beautifully appointed gourmet kitchen, featuring commercial-grade appliances, gas cooking and generous gathering spaces, is equally suited for intimate evenings and memorable celebrations. Imagine Thanksgiving overlooking the water, Christmas beside the fireplace and summer evenings entertaining friends on the expansive decks as boats make their way home. Here, every season offers something beautiful to enjoy. The luxurious waterfront primary suite provides a peaceful sanctuary with its own sitting room, fireplace, custom walk-in closet and beautifully appointed spa bath. Generously proportioned additional bedrooms welcome family and guests, while the finished walk-out lower level offers a recreation room, wet bar, wine storage, fitness room, fifth bedroom and full bath. A glass-enclosed sunroom overlooking the water provides another inviting place to relax and appreciate the surroundings. Outdoor living is equally exceptional. Expansive multi-level decks invite elegant entertaining, leisurely dining and quiet mornings overlooking the harbor. Nearly two acres of beautifully landscaped grounds offer privacy and serenity within one of Annapolis' most desirable waterfront communities. Recent improvements, including a new septic system and advanced whole-house water treatment with reverse osmosis and ultraviolet purification, provide additional comfort and peace of mind. Residents of Downs on the Severn enjoy access to two private marinas, a waterfront clubhouse, swimming pool, tennis and pickleball courts, all conveniently located near Historic Annapolis, wonderful restaurants and shopping, and major commuter routes to Baltimore and Washington, D.C. A magnificent deep-water setting, an extraordinary private pier and a beautifully appointed home designed to embrace the waterfront lifestyle. At 1486 Downham Market, the beauty of the Severn River is not simply a view. It is a way of life.

1486 Downham Market, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

4709 Coastal Highway Unit 555, Ocean City
$349,900
2 Beds ⋅ 2 Baths
Welcome to Wight Bay South, where waterfront living, breathtaking sunsets, and the ultimate Ocean City beach lifestyle come together in one exceptional property. Perfectly located in the heart of Midtown Ocean City, this beautifully furnished 2-bedroom, 2-bath waterfront condominium offers direct bay access, peaceful canal views, incredible boating opportunities, and is just one short block from the Atlantic Ocean and sandy beaches. Wake up each morning with a cup of coffee on your private fifth-floor balcony as boats gently cruise through the canal, the sounds of seagulls drift through the coastal air, and the refreshing bay breeze reminds you why life at the beach is unlike anywhere else. Spend your days relaxing on the beach, boating on the Isle of Wight Bay, kayaking or paddle-boarding through the calm canals, fishing from the community pier, or simply soaking up the sun beside the bayfront pool. As evening falls, unwind with breathtaking waterfront sunsets that paint the sky in brilliant shades of orange, pink, and purple while reflecting across the tranquil bay. Inside, you’ll discover a bright, open-concept floor plan designed for effortless coastal living and entertaining. The spacious living area and primary suite both open to the oversized waterfront balcony through double sliding glass doors, creating the perfect indoor-outdoor lifestyle and allowing natural light and beautiful water views to become part of your everyday experience. The well-appointed kitchen offers generous counter space and a convenient pass-through to the dining area, making entertaining family and friends effortless. Offered fully furnished, this turnkey property is ready to enjoy from day one or continue as a successful vacation rental. Wight Bay South offers resort-style amenities, including a waterfront outdoor pool overlooking the bay, pier and dock access, a mooring area (subject to availability), elevators, extra storage (subject to availability), under-building and permit parking, professionally maintained common areas, and onsite management. Located in one of Ocean City’s most desirable Midtown neighborhoods, you’re within walking distance of the beach, waterfront dining, shopping, entertainment, marinas, and local favorites, while enjoying the peace and tranquility of a waterfront community tucked away from the crowds. Whether you’re searching for a waterfront vacation home, a second home, or a proven income-producing investment property with approximately $50,000 in annual rental income potential, this exceptional condo offers the perfect combination of location, lifestyle, and opportunity. Come experience why so many people fall in love with Wight Bay South—and why every day here feels like a vacation.

4709 Coastal Highway Unit 555, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact:

500 Sara Dr, Annapolis
$1,395,000
4 Beds ⋅ 3 Baths
Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless potential to make it your own. Whether you're looking to move right in and enjoy the home as it is or reimagine the space into your dream retreat, this property presents an incredible opportunity in one of Annapolis' most sought-after waterfront communities. Designed to embrace its natural surroundings, the home is filled with light and features soaring ceilings, warm wood architectural details, and expansive windows that bring the outdoors in. The dramatic living room is anchored by a striking brick fireplace and flows into the dining area and kitchen, creating an inviting space for gathering. Three sets of sliding glass doors open to the expansive balcony, seamlessly blending indoor and outdoor living while framing peaceful water and woodland views. Just beyond, the enclosed porch with vaulted ceilings provides a year-round place to relax while taking in the peaceful water and woodland views. The thoughtfully designed main level offers two bedrooms, including a spacious primary suite with a private sitting area and ensuite bath, along with a second bedroom that is served by a full hall bath, ideal for guests, family, or a home office. The walkout lower level expands the living space with a generous family room featuring a second fireplace, a built-in bar area, and access to the adjoining sunroom and patio, creating the perfect setting for entertaining. Two additional bedrooms are located on this level, including one with a private ensuite bath and private patio. An additional bedroom offers flexible accommodations for guests or multigenerational living. Life in Saefern is about much more than the home itself. Membership in the renowned Saefern Saddle & Yacht Club (SSYC) includes a boat slip, marina, swimming pool, tennis and pickleball courts, horse stables, dog park, playground, and an active community lifestyle. Just minutes from Historic Annapolis, the U.S. Naval Academy, shopping, dining, and convenient commuter routes to Washington, D.C. and Baltimore, this is a rare opportunity to invest in a home with outstanding bones, water views, and the chance to create something truly special. Welcome Home!

500 Sara Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

12316 Savanna Ct, Bishopville
$1,125,000
4 Beds ⋅ 4 Baths
Cottage-style, picture perfect home. Located on a beautiful tidal pond with unobstructed open views of water, marsh, golf course, and offers significant privacy. (UPDATE REGARDING TIDAL POND! LAST SATURDAY DURING MY OPEN HOUSE WHILE OUT ON BACK DECK WITH VISITORS, MUCH TO OUR SURPRISE, THERE CAME TWO KAYAKERS OUT OF THE MARSH 'S TIDAL CREEK! ASKED WHERE THEY CAME FROM, THEY SAID FROM THE ROUTE 90 BRIDGE. ASKED HOW DEEP THE POND IS, THE KAYAKER IN THE MIDDLE PUT HIS PADDLE DOWN AND SAID THE POND WAS HIGHER THAN THE PADDEL; ABOUT 7 FEET+- DEEP AT HIGH TIDE. THE ONE CLOSER TO THE SHORELINE SAID HE THOUGHT IT WAS AROUND 3-4 FEET!) No one can build on the lot next door on right side of house. Meticulously maintained and so many updates and improvements have been made. Kitchen offers French Vanilla-colored custom cabinetry with PLENTY of cabinet space and walk-in pantry. Island features a maple cutting board counter top and granite flanks the other counters. Great room has 20' ceiling and a wall of windows overlooking, both, the water and exquisite English country garden landscaping. (seller is an avid and expert gardener and has more than 70 hydrangeas) Great room also offers a gas fireplace and STARK-brand carpeting featuring their "antelope" design plus Hunter-Douglas remote-controlled window blinds. Gas heat w central air on first floor and heat pump second level. Separate heat pump for the sun room! Formal dining room offers a beautiful electric fireplace with hand-painted tiles, and invites you to USE the dining room. Laundry room separates the garage from the living area of the house. THIS laundry room is definitely extra-large and the space takes full advantage of cabinet storage. Flooring in laundry room and sunroom is heated. Floors in both of these rooms are honed white limestone and mixed with Belgium blue (almost black) stone. Primary bedroom on second level offers a private balcony overlooking the natural views of wetlands, water, and wildlife. Primary bedroom is large enough to accommodate an adjoining sitting room. And next is the primary bath... the home's signature statement. Walk-in shower with a 5 X 7 hand-painted custom tile mural features a chinoiserie interpretation of the property's surrounding waterfowl and coastal landscape. Calacatta Gold marble basketweave flooring, dual shower heads, and a rain shower all by Newport Brass, and accented by a brass shower door handle developing a rich patina over time. Heated tile floors, antique delft light fixture, and claw foot soaking tub with unlacquered Newport brass fixtures including a nostalgic telephone-style hand sprayer! Two walk-in closets with California closet interiors in the primary suite and found in other closets as well. Three additional bedrooms - one with its own private full bath... Now it's YOUR TURN to look at the rest of this cottage-inspired, enchanted space because the list of amenities and features this one-of-a-kind home offers is endless. (But that list will be available for you inside the home!!) ANOTHER SPECTACULAR FEATURE OF THIS CUSTOM HOME IS THE VIEW OF THE LONGEST GOLF CART BRIDGE IN THE U.S. THAT IS APPROXIMATELY 1,500 FEET!! This house has it ALL! Views, Tidal waterfront pond, location, and an upscale English cottage-style home...LOCATION, LOCATION, LOCATION!!

12316 Savanna Ct, Bishopville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

2724 Holly Beach Rd, Baltimore
$849,900
3 Beds ⋅ 2 Baths
No expense was spared in the complete transformation of this extraordinary waterfront residence! Buyers will appreciate the luxury features, functionality, and timeless craftsmanship that come together to create a truly one-of-a-kind home. Thoughtfully designed for both everyday comfort and long-term living, the home offers accessibility and "aging in place" features including a first-floor bedroom and full bath, widened doorways, barrier-free bathrooms, wheelchair-friendly kitchen design, and future-ready accommodations for additional accessibility upgrades. Every detail was carefully considered—from the maintenance-free exterior materials and Anderson 400 Series Low-E windows strategically positioned to maximize breathtaking water views, to the custom cabinetry, imported Italian tile, Dekton countertops, and stunning quartzite finishes. The gourmet kitchen is equipped with GE Café smart appliances, a Zephyr range hood, custom cabinetry with premium storage solutions, and thoughtful features including a hands-free water-saving foot pedal and concealed power outlets. The home seamlessly blends luxury with cutting-edge technology. App-controlled smart home systems allow remote operation of the lighting, motorized shades, HVAC, security, cameras, Yale WiFi lock, heated bathroom floors, water heater, and major appliances from virtually anywhere in the world. Lutron RadioRA 3 lighting creates customizable scenes throughout the home, while designer lighting, under-cabinet illumination, and a dramatic porcelain fireplace wall provide an inviting atmosphere day and night. The spa-inspired bathrooms feature heated porcelain floors, Toto Washlet bidets, custom vanities, ultra-quiet automatic moisture-sensing ventilation, and elegant wet-room designs that are both beautiful and exceptionally easy to maintain. Outdoor living is equally impressive. Enjoy spectacular waterfront sunsets from the maintenance-free deck beneath the motorized Sunsetter awning or head to the private dock, complete with electricity, water, fish-cleaning station, dock box, Marina Mate system, and a 10,000-pound Hi-Tide boat lift. Additional thoughtful upgrades include spray foam insulation, gutter guards, an insulated attic, powered workshop shed, raised garden beds, multiple exterior hose bibs with interior shutoffs, and countless energy-efficient enhancements throughout. Adding to the home's unique character, the current owners thoughtfully preserved pieces of its rich history, incorporating original hardware, historical photographs, and even the property's original 1920s rental agreement into the renovation as a tribute to the home's remarkable legacy. Furniture, décor, kitchenware, tools, and numerous additional items are available for purchase separately, offering the opportunity to enjoy this exceptional waterfront retreat exactly as it has been curated. A comprehensive list of custom upgrades, smart home features, specialty finishes, and construction details is available upon request. This is a home that simply must be experienced in person to fully appreciate the extraordinary level of planning, craftsmanship, and investment that went into every detail.

2724 Holly Beach Rd, Baltimore

Listing courtesy of EXP Realty, LLC. Contact:

16351 Tanyard Rd, Upper Marlboro
$1,495,000
4 Beds ⋅ 3 Baths
Extraordinary Waterfront Equestrian Estate on 23+ Private Acres is now available for the first time ever. Nestled on a private peninsula at the confluence of the Tanyard and Hotchkins tributaries, this remarkable, beautifully landscaped, well-maintained 23+ acre waterfront estate offers an unmatched combination of luxury living, premier equestrian amenities, and exceptional privacy. The custom-built 4-bedroom residence showcases superior-quality finishes throughout, a breezy covered porch, a TimberTech deck overlooking the waterways, a cozy masonry fireplace, spacious living areas, and an attached 24' x 24' two-car garage. The home also features a full walk-out basement encompassing approximately 1,304 square feet, with exterior windows and door access and more than 8 feet of headroom, offering tremendous potential for additional living space, recreation, or storage. Designed for the serious equestrian in mind, the property's impressive horse facilities include a 204' x 70' indoor riding arena featuring a 20m x 60m dressage ring with Pure Coarse Sand footing, four-speaker Bose PA system, ring sprinkler system, 92 linear feet of training mirrors, and spectator seating area. A separate, detached horse barn offering seven 12 X 12, matted stalls with electric outlets for fans or water heaters, hot and cold-water wash rack, tack room, 12’ wide, self-draining center aisle, hay loft, and an adjacent 11' x 24' enclosed horse trailer garage. The barn offers direct access to four fenced, lush grazing fields enclosed with three-board fencing, and also offers an all-weather heavy use pad in the paddock adjacent to the barn to stabilize footing in wet weather. There is also a 12' x 24' run-in shed for your horses' security and comfort. Supporting the farm operation is a detached 20' x 58' five-bay equipment building, a concrete manure structure, a wood shed, and an exceptional four bay 24' x 44' detached two-story garage/workshop complete with a wood stove, providing abundant space for equipment, vehicles, hobbies, or storage. Whether you're seeking a private waterfront retreat, a turnkey equestrian facility, or a legacy property, this rare offering in Land Preservation with low Agricultural Assessment and taxes, delivers an unparalleled lifestyle in a breathtaking natural setting at an amazing price with water, wineries and history at your front door. Appointment only. Cannot be seen from the road. Call today!

16351 Tanyard Rd, Upper Marlboro

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

325 Markwood Dr, Oakland
$769,000
4 Beds ⋅ 4 Baths
LAKEFRONT 4BR, 3.5BA log home with over 3300sf and 4.35 acres of privacy! Lovingly maintained property with gorgeous views of the 10 acre lake from almost every room in the house! Peaceful surroundings with towering mature trees and just enough yard space in a very laid back, rural setting near Herrington Manor and Swallow Falls state parks. If that weren't impressive enough, Meadow Lake Estates community is adjacent to 598 acres of DNR / state land fronting on the Youghiogheny River. Set up for one level living - bedroom suite and laundry room on first floor. Features include whole-house generator, wood-burning fireplace, a recently finished basement adding a game room and a fourth bedroom, front and rear decks (trex on back deck), covered porches, fire-pit, wrap-around driveway and a spacious loft that serves as a third living room. Must see to appreciate the solitude of this fantastic home! Furnishings negotiable. Short term rentals are not permitted in this community.

325 Markwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

8601 Chesapeake Dr, Ocean City
$2,999,000
This is a once in a lifetime opportunity to own an undeveloped southern exposure bayfront parcel of land in Ocean City, MD. Enjoy incredible sunsets from your home once this property is developed and live a convenient relaxing lifestyle with a short walk or bike ride to the beach. Sale also includes the bay view parcel located at 401 Bering Road directly behind the bayfront parcel. Buyer has the option to build two homes, one on each separate parcel or build an estate over the entire parcel. Buyers should rely on the recorded subdivision plat attached to the listing for lot line placement. Yellow perimeter lines in pictures are not exact representation of lot lines. No builder tie-in but ask listing agent about building plans that have already been designed and fitted to this stunning property.

8601 Chesapeake Dr, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact:

274 Capote Ct W, Severna Park
$1,297,400
4 Beds ⋅ 4 Baths
NEW PRICE POSITIONING! BACK ON THE MARKET AND READY TO SHOW! Now offered at $1,297,400 following another significant price adjustment, this extraordinary waterfront estate presents a renewed opportunity in prestigious Stewart’s Landing. Where refined coastal living meets premier deep-water access, this beautifully maintained residence is privately positioned along Old Man Creek with a direct route to the Magothy River and Chesapeake Bay. Extensively renovated and thoughtfully updated, the property offers an exceptional blend of elegance, privacy, comfort, and boating appeal seldom available in Severna Park. Offering three fully finished levels, more than 3,300 finished square feet, four bedrooms, and three-and-a-half baths, the home features a versatile floor plan designed for everyday living, elegant entertaining, and multigenerational needs. Two private bedroom suites—one on the upper level and one on the fully finished lower level—provide ideal accommodations for extended-stay guests, an au pair, or additional family members. The walkout lower level includes a separate exterior entrance and opens directly to a lighted paver patio with ceiling fans, providing exceptional privacy and a seamless extension of the home. At the heart of the residence is a true gourmet chef’s kitchen with premium finishes, including a built-in Sub-Zero side-by-side refrigerator and freezer, Wolf dual-fuel range with six burners, griddle, dual ovens and range hood, plus a KitchenAid dishwasher. Upgraded cabinetry, granite countertops, copper sinks and fixtures, tile flooring, and generous gathering spaces complete this impressive culinary setting. Beautifully renovated baths include a luxurious primary bath, an extensively updated lower-level suite bath, and additional upper-level bath improvements. Newer carpeting, lower-level luxury vinyl flooring, a custom stairway railing, solar skylights with automatic rain closure, and carefully selected finishes further enhance the home’s sophisticated presentation. The private pier is designed for the serious boating enthusiast and features a 20,000-pound boat lift, replaced pilings, and buried water, electrical, and communication lines extending from the residence to the waterfront. A dedicated outdoor electrical subpanel supports the pier and ground lighting. Located on the expansive deck just off the main level, the fully equipped outdoor kitchen elevates waterfront entertaining with hot and cold running water, a 48-inch gas grill, two side burners, refrigerator, ice maker, and granite countertops. The exterior is equally impressive, featuring Hardie siding, a stone façade, mahogany front door with sidelights, architectural enhancements, and extensive professional landscaping. Engineered retaining walls, irrigation and drainage systems, landscape lighting, and an invisible dog fence enhance both beauty and function. The renovated garage offers an epoxy floor, slat-wall storage, and a polished appearance. Additional major improvements include a newer roof, updated HVAC components, LeafFilter gutter protection with a transferable lifetime warranty, and numerous structural, mechanical, and cosmetic enhancements. This extraordinary property presents a rare opportunity to experience exceptional waterfront living where boating, entertaining, privacy, and timeless elegance come together. From mornings on the pier to evenings overlooking the water, every detail has been thoughtfully designed to create an exceptional Chesapeake Bay lifestyle. Conveniently located near premier shopping, parks, the B&A Trail, dining, and major commuter routes, including I-97, Route 32, Route 50, I-95, I-295, and I-495. Its proximity to Washington, D.C., Northern Virginia, Baltimore, Fort Meade, NSA, DISA, and BWI Airport makes it ideal for both government and private-sector professionals.

274 Capote Ct W, Severna Park

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

47558 Lucas Cove Ln, Lexington Park
$499,000
3 Beds ⋅ 2 Baths
Welcome to 47558 Lucas Cove Lane, where peaceful waterfront living meets endless potential. Tucked away on a private, wooded double lot overlooking scenic Lucas Cove, just off the beautiful St. Mary's River, this charming 3-bedroom, 2-bath home offers a rare opportunity to enjoy the best of Southern Maryland's waterfront lifestyle. Designed to maximize its exceptional setting, the home is surrounded by expansive water views and boasts an impressive amount of linear shoreline, creating a tranquil backdrop for everyday living. Whether you're sipping your morning coffee while watching the sunrise over the cove, entertaining family and friends, or simply enjoying the serenity of nature, this property delivers the privacy and waterfront experience you've been searching for. Inside, the home offers comfortable living spaces filled with natural light, while the unfinished second story presents an incredible opportunity to expand. Create additional bedrooms, a luxurious primary suite, a home office, or a recreation space—the possibilities are limited only by your imagination. The oversized double lot provides room to relax, garden, or further enhance the property, all while enjoying the peaceful surroundings and abundant wildlife. Conveniently located just minutes from marinas, restaurants, historic St. Mary's City, and Leonardtown, this waterfront retreat offers the perfect blend of seclusion and accessibility. Whether you're looking for a full-time residence, a weekend getaway, or a waterfront property with room to grow, 47558 Lucas Cove Lane is a rare opportunity to own a slice of paradise on the St. Mary's River. Schedule your private showing today and discover everything this exceptional waterfront property has to offer.

47558 Lucas Cove Ln, Lexington Park

Listing courtesy of Infinitas Realty Group. Contact:

206 Harbor Dr, Lusby
$1,249,900
4 Beds ⋅ 6 Baths
Welcome to your over 4500 sq ft dream waterfront on the deep, navigable waters of Mill Creek! A show-stopping Mediterranean masterpiece with an almost 200 ft pier… bring ALL the water toys! Every inch of this one-of-a-kind waterfront estate was designed for elegance, entertainment, and effortless living. Step through the grand mahogany doors and immediately take in the sweeping water views that frame the heart of the home. The main level showcases rich exotic Bubinga wide-plank flooring, custom built-ins, and open, light-filled spaces that invite you to gather, dine, and unwind. Tray ceilings with built-in lighting and abundant recessed lights set the perfect mood. The inviting family room features a gas fireplace, built-in shelving, and captivating views of the water. The gourmet kitchen is as stunning as it is functional… featuring travertine flooring, inset cabinetry, and professional-grade top-of-the- line appliances including Sub-Zero, Wolf, and Miele. Just beyond, the multiple living areas open to expansive decks overlooking the water — perfect for morning coffee or sunset cocktails. The entire second level is dedicated to the primary suite, offering two private balconies, a wet bar and beverage center, office area, spacious sitting area, dual closets, and a spa-inspired bath complete with heated travertine floors, a soaking tub, and a walk-through shower with a steamer. The upper level includes three spacious bedroom suites, each with their own private bath and gorgeous water views. Bring the party to the basement level where the memories are made — an entertainer’s dream with a custom bar, media and game spaces, and a private saltwater plunge pool and spa that can be enjoyed year-round. The pier includes two slips, a 12-ft boat lift, 50-amp shore power, and approximately eight feet of water depth, ideal for all the boating and waterfront adventures. With thoughtful details throughout, this home offers many other luxury features such as an elevator, generator, high efficiency 3-zoned HVAC with separate controls per room, 10 and 9 ft ceilings throughout, Ipe decking, tons of outdoor hardscaping, speaker system throughout entire house, and a laundry chute! Additional nearby lot with a shed for storage and water toys convey. A rare opportunity to own a remarkable waterfront residence that effortlessly blends luxury, comfort, and coastal living. Welcome to the good life on Mill Creek!

206 Harbor Dr, Lusby

Listing courtesy of CENTURY 21 New Millennium. Contact:

8612 Tilghman Island Rd, Wittman
$5,995,000
8 Beds ⋅ 6 Baths
See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

8612 Tilghman Island Rd, Wittman
$7,900,000
8 Beds ⋅ 6 Baths
"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

8612 Tilghman Island Rd, Wittman
$5,995,000
8 Beds ⋅ 6 Baths
See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

Jennings Lane, Darlington
$134,900
1 Beds ⋅ 2 Baths
Fully furnished, 2-level cabin with 1,200 sq. ft. of living space on the Broad Creek. The cabin is located about 1/4 mile from the Broad Creek Public Boat Landing and 1/4 mile from the Susquehanna River. There are approximately 60 steps from the parking area to the cabin. The first level has a large kitchen area and family room area with a hidden murphy bed and views of the Broad Creek. The second level has a living room with bar area, pull-out sleep sofa, and large windows to view the Broad Creek; bedroom with a double bed, single bed, and a closet; full bathroom with shower, and a half bath. There is a large, newer deck from the living room and deck near the water. Updates include a newer roof, large front deck, hand rails on the main stairs to the cabin and to the water, brand new septic holding tank system, all new plumbing, new water heater and new electric and electric main panel. The cabin has passed all inspections by both Harford County and Constellation Energy. After nearly 50 years in the owner's family, the Seller is now ready to sell this cabin to the next new owner. Seasonal use, only. Cannot be used as a permanent residence. Please note that you are not buying the land. You are purchasing a Leasehold interest with Constellation Energy Generation LLC. This property is likely not eligible to be used as collateral for a mortgage. See MLS docs for detailed brochure which includes the cottage program rules and regulations with Constellation Energy. The Owner or the Owner's representative must attend all showings.

Jennings Lane, Darlington

Listing courtesy of O'Neill Enterprises Realty. Contact:

101 Main, Secretary
$369,900
3 Beds ⋅ 4 Baths
Waterfront living at its best! This home features 3 bedrooms and 3.5 bathrooms which includes 2 primary suites allowing your guests to have an in-suite bathroom. The property also has 2 private decks overlooking the Warwick River and a pier with a recently installed boat lift. This unit was built in 2001 and has a sprinkler system, a large family room with a gas fireplace, new roof and a new boardwalk is being installed soon. The home is in very good condition and ready to move into. Enjoy beautiful sunsets and quick access to the Choptank River and Chesapeake Bay. There are many nearby beaches, restaurants and shopping. This is a must see!!

101 Main, Secretary

Listing courtesy of The Glocker Group Realty Results. Contact:

Robinwood Dr Unit 9, Oakland
$175,000
Rare riverfront building lot on the Youghiogheny river offering 175+ feet of water frontage on 3.46 acres. Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. Enjoy a picturesque setting in a riverfront setting with NO HOA restraints. Perc approved. While parts of this lot may be in the flood plain, the building envelope for a home IS NOT in the flood plain.

Robinwood Dr Unit 9, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

251 Robinwood Dr, Oakland
$750,000
5 Beds ⋅ 5 Baths
One-of-a-kind Youghiogheny riverfront estate offering 224 feet of water frontage . Soak in the sounds of the flowing waters and chirping birds, cloaked in a private canopy of mountain laurel, pine trees and mature hardwoods. 5BR 4.5 BA log masterpiece with attached 2 car garage and paved driveway. Thoughtful design and well maintained with spacious suites, floor to ceiling fireplace, log accent walls and exposed beams. Features include multiple fireplaces (wood & gas), Andersen doors & windows, trex decking, hardwood floors, metal roof, custom cabinets in kitchen & bedroom suites, eat-in kitchen, and sold furnished! Enjoy a picturesque setting in a riverfront setting with NO HOA restraints for this home. Seller also offering an adjacent unbuilt riverfront lot (#9) for $175,000 MLS #MDGA2012380

251 Robinwood Dr, Oakland

Listing courtesy of Taylor-Made Deep Creek Sales. Contact:

13535 Marine Ave, Lusby
$785,000
3 Beds ⋅ 2 Baths
Welcome to this exceptional waterfront retreat on Marine Avenue, privately nestled on a point of land overlooking Old School House Cove and Mill Creek. A tree-lined drive brings you in with ample parking, storage shed, and excellent privacy. Inside, approximately 2,147 square feet of living space, including four bedrooms, two full baths, a spacious great room with 180-degree water views, a gourmet kitchen, large dining area, and a convenient laundry room. Enjoy the rear deck with sweeping views of Mill Creek and Old School House Cove. A gentle walkway leads to a waterside fire pit, perfect for evening boating watching.The private pier accommodates two vessels, and the property is just minutes to historic Solomons Island by boat Sail or power, and approximately 1 hour to Annapolis and the D.C. area. 1.5Hours to international airport.

13535 Marine Ave, Lusby

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

1713 Doeller Rd, Fishing Creek
$2,950,000
Looking for a business opportunity, want to expand your business? This exceptional property offers outstanding income and business potential, including opportunities for a private retreat, vacation rental, event or wedding venue, guided hunting and fishing, sporting clay, kayak, water sports experiences and other outdoor recreational offerings. Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact:

7432 Old Battle Grove Rd, Dundalk
$275,000
Waterfront Lifestyle Buyers & Investor/Builder Alert! The time to act is now. This rare Baltimore County DR 5.5 zoned undersized waterfront lot offers an exceptional opportunity to possibly build your dream home or investment property on the peaceful waters of Bear Creek. The existing dwelling has already been razed, and public water and sewer are available and capped on the property, providing an excellent starting point for your new construction project. Lifestyle Buyers, have you been touring Baltimore County waterfront homes but can't seem to find one that checks all the boxes? Why settle for something you may not like fully when you can design and possibly build exactly what you've envisioned? This outstanding waterfront homesite provides the perfect opportunity to construct your custom primary residence with space possible for a future in-law residence or ADU as well as a luxury weekend retreat or investment property while enjoying spectacular sunset views over Bear Creek. Financing or cash options are welcome. Buyers may be able to obtain a construction-to-permanent loan with as little as 10% down, allowing you to build the home of your dreams. Or bring your cash and build on your own timeline. The property 7432 OBG includes an existing private pier with a boat lift and (PWC) lift. The shoreline is improved with a combination of marine-treated timber bulkhead and riprap. Known as 7432 Old Battle Grove Road, this property is identified as Tax ID #1504200691 (Lot 26) and offers approximately 11,644 square feet (.26 acres) of upland area in which the majority of land is in Flood Zone X. For buyers seeking additional waterfront frontage and development potential, this parcel may also be purchased together with the adjacent vacant waterfront lot on the right looking at the water, offered separately in the MLS Lot Land section as Old Battle Grove Road, identified as Tax ID #04151700005719, consisting of portions of Lots 27 & 28, containing approximately 15,070 square feet (.34 acres) and currently offered at $275,000.00 as well. The seller is willing to sell both side-by-side waterfront parcels together as one package for $524,900, creating an outstanding assemblage opportunity or keep the properties separate. If combined, the properties offer tremendous flexibility and redevelopment potential. Build an impressive waterfront estate, create a compound with multiple dwellings (subject to all governmental approvals including variances), develop new construction homes for resale, or hold as a long-term investment. Opportunities to acquire neighboring waterfront parcels with this level of flexibility are increasingly rare. Buyers are responsible for verifying all zoning regulations, planning requirements, Chesapeake Bay Critical Area regulations, permitting requirements, engineering lot line adjustments if needed and all other governmental approvals at the buyer's sole expense. Each Lot Land listing is to be sold as is and each is to remain buildable at the Buyers expense in lines need adjusted per requirements. Bear Creek is well known for its protected deep water, excellent boating, fishing, crabbing, kayaking, paddleboarding, swimming, and abundant wildlife. Enjoy all the benefits of waterfront living with the convenience of your own private pier and no marina fees. Conveniently located with easy access to I-695, I-95, Baltimore City, Tradepoint Atlantic, Canton, Johns Hopkins Bayview, neighborhood marinas, waterfront restaurants, hiking and biking trails, and numerous waterfront parks. Whether you're looking to build your forever home, weekend getaway, or your next investment project, this exceptional waterfront opportunity deserves your attention. The lot lines depicted in the photos are an approximation of record.

7432 Old Battle Grove Rd, Dundalk

Listing courtesy of RE/MAX Advantage Realty. Contact:

9900 Coastal Hwy Unit 1604, Ocean City
$579,900
2 Beds ⋅ 2 Baths
This 2-level, 1,260 sq. ft. condo on the 16th floor of Century I offers the best of both worlds with breathtaking ocean and bay views, allowing you to enjoy spectacular sunrises over the Atlantic and stunning sunsets across the bay. Opportunities like this are rare, as few Century I residences feature an oceanfront bedroom. Wake up each morning to endless ocean views from the spacious primary bedroom, highlighted by a beautiful tropical mural and an entire wall of windows that fills the room with natural light. The oceanfront living room also captures panoramic water views and opens to a private balcony overlooking the beach, creating the perfect place to relax with the sights and sounds of the ocean. The second bedroom offers equally impressive bay views and its own private balcony, providing a peaceful retreat to enjoy unforgettable sunsets. Lovingly maintained and gently used, this unique residence is ready for its next owner to create lasting beach memories. Recent improvements include a new heating and air conditioning system in 2025, along with new vanities and mirrors in both bathrooms, also completed in 2025. Century I is one of Ocean City's premier oceanfront buildings, offering an impressive collection of amenities including multiple elevators, an indoor pool, fitness center with sauna, on-site management, security, and a welcoming oceanfront lobby. The condo fee also includes streaming DirecTV for added convenience. The unit also comes with its own large private storage locker located on the ground level ($35 per year fee), if buyer wants it. Located in the heart of midtown Ocean City at 99th Street, you'll be just moments from popular restaurants, shopping, the public library, dog park, playground, public basketball and tennis courts, and only a short drive to Northside Park. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this rare Century I condo delivers an unbeatable combination of location, views, and lifestyle.

9900 Coastal Hwy Unit 1604, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact:

43816 Raspberry Ln, Hollywood
$724,986
3 Beds ⋅ 4 Baths
Experience timeless English Tudor character paired with sweeping, unobstructed views of the Patuxent River. From the moment you step inside, the home’s expansive windows frame miles of serene waterfront, filling each room with natural light and a sense of calm that only riverside living can offer. With three bedrooms plus a dedicated office, the layout balances comfort and functionality Ideal for a full‑time residence or a peaceful weekend retreat. The original portion of the home features a classic kitchen, while the thoughtfully renovated section adds a second kitchen, offering flexibility for entertaining, multigenerational living, or reimagining the space to suit your vision. A two‑car garage and an unfinished basement currently used as a workshop provide abundant storage and room for hobbies, projects, or future expansion. Whether you dream of crafting the perfect waterfront getaway or designing a year‑round sanctuary, this property is ready to become your canvas. Beyond the walls of the home, the property invites you to fully embrace the natural beauty and recreation the Patuxent River is known for. Hunt for age‑old shark teeth along the shoreline, harvest oysters straight from the water, and enjoy crabbing during warm Maryland seasons. Whether you’re an outdoor enthusiast or simply love the idea of stepping into a slower, more peaceful rhythm, this location offers experiences you won’t find anywhere else. Waterfront living is within reach. Come experience the view, feel the tranquility, and imagine the possibilities waiting for you here.

43816 Raspberry Ln, Hollywood

Listing courtesy of O'Brien Realty ERA Powered. Contact:

405 Bayshore Dr Unit 304, Ocean City
$490,000
2 Beds ⋅ 2 Baths
Waterfront Living with Your Own Private Boat Slip! Discover the perfect blend of relaxation and recreation in this beautifully maintained 2-bedroom, 2 bathroom bayfront condo in Ocean City, MD. Offering breathtaking bay views, a private deep water boat slip, deep channel and excellent fishing ,crabbing and clamming right outside your door, this property is an ideal choice for boaters, anglers, vacationers, or anyone seeking the ultimate coastal lifestyle. Step inside to a bright, open floor plan designed for comfortable living and entertaining. The spacious living and dining areas open onto a private balcony overlooking the bay, providing the perfect setting to enjoy your morning coffee, watch spectacular sunsets, or simply take in the peaceful waterfront scenery. The primary suite features a private en-suite bath and ample closet space, while the second bedroom and full guest bath offer comfortable accommodations for family and friends. The well-equipped kitchen provides plenty of cabinet space and overlooks the main living area, making it easy to entertain. Bring your boat and take advantage of your private boat slip, offering quick and easy access to the bay for boating, paddleboarding, kayaking, and water sports. Fishing enthusiasts will appreciate the excellent fishing opportunities just steps from the condo, making it easy to cast a line whenever the mood strikes. Conveniently located just minutes from Ocean City's pristine beaches, famous boardwalk, restaurants, shopping, golf courses, and entertainment, this exceptional waterfront condo offers the best of both worlds peaceful bayfront living with all the excitement of Ocean City nearby. Whether you're looking for a full-time residence, a vacation retreat, or possible income potential this bayfront gem is ready to help you make unforgettable memories on the water.

405 Bayshore Dr Unit 304, Ocean City

Listing courtesy of J&B Real Estate. Contact:

Island Dam, Clear Spring
$150,000
Rare opportunity to own 50% Tenant in common interest in a private island on the Potomac River along the C&O Canal, The chain 3 of islands consisting of 108 +/- acres (see tax card), Ideal for recreation, camping, hunting, fishing and boating, featuring mature Willow and Sycamore trees, sandy beaches, the islands and surrounding river banks are nesting grounds for Mallard Ducks, Canadian Geese and Blue Heron. CSX Railroad owns the other 50% tenant in common interest . Purchaser shall hold Seller harmless from obtaining the other 50% interest from CSX Railroad. Call for more details

Island Dam, Clear Spring

Listing courtesy of Mackintosh, Inc.. Contact:

205 Somerset St Unit 403B, Ocean City
$479,350
1 Beds ⋅ 2 Baths
Major Price Improvement! Top-floor direct-bay condo with proven rental history of over $35K/season. Stunning bay & marina views at White Marlin Condos – Somerset Street, Ocean City, MD This beautifully maintained 1-bedroom, 1.5-bath condo at White Marlin offers the perfect blend of comfort, convenience, and strong investment potential in the heart of Ocean City. Located on Somerset Street, this unit boasts breathtaking panoramic views overlooking the marina and Assawoman Bay, providing a serene waterfront backdrop from your private balcony or living area. Inside, the condo features stylish granite countertops and beautiful tile flooring, creating a bright, modern, and low-maintenance living space. The open layout maximizes natural light and makes entertaining effortless. The primary bedroom offers ample closet space and direct access to the updated full bathroom, while the convenient half-bath serves guests perfectly. Proudly well-maintained by its current owners, this unit is move-in ready and has a proven track record of excellent rental revenue. Whether you're looking for a personal coastal getaway or a turnkey investment property, this condo delivers year-round appeal with easy access to the beach, boardwalk, restaurants, and all the attractions Ocean City has to offer. Property has one assigned parking spot.

205 Somerset St Unit 403B, Ocean City

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact:

6 Walton Way, Mc Henry
$1,199,995
4 Beds ⋅ 4 Baths
In the hub of McHenry, this is the perfect spot to begin making memories in Deep Creek! Schedule an appointment now to explore and appreciate the convenience of this location. This is an excellently maintained 4-bedroom, 4-bath home. Incredible water and mountain views in this exclusive 4-unit single home/condo community! The property offers multiple living areas, a main-level bedroom and bath, and a gourmet kitchen designed for both functionality and style. This turn-key property is move-in ready, providing a seamless blend of comfort and relaxation. Enjoy the scenery and activity from your doorstep while taking advantage of the spacious layout. The current owner added board-on-board fencing for privacy and the "plus" of a detached 2-car two story oversized garage with 10' ceilings and two 9'x10' garage doors. This is the ONLY home in the Walton's Landing community with a garage! Extra upgrades for the garage include LED lighting, 2 remotes for WiFi-Smart automatic doors and a gas line hook-up for heat if desired. There are interior stairs for access to the upper level of the garage with 8' ceilings in that space. Just steps away is your dedicated dock slip for your boating pleasure and all summertime water activities! Recent additional upgrades include full exterior paint and paving of driveways. Enjoy the proximity to Wisp Resort, the variety of lake area dining options, hiking, biking, and sightseeing at our beautiful state parks, and fun activities for all ages! Don't miss this opportunity to own this lakefront getaway!

6 Walton Way, Mc Henry

Listing courtesy of Railey Realty, Inc.. Contact:

1713 Doeller Rd, Fishing Creek
$2,950,000
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact:

12505 Potomac View Dr, Newburg
$274,900
Waterfront lot on the Potomac River! Perced and ready to build your dream home on 1.7 acres with a sandy beach (during low tide). Wake up every morning and take in gorgeous views and sunsets. The house site is slightly elevated allowing for a possible walk-out basement. Build a pier over the water where you can keep your boat and jet ski's. Whether this is your year-round home or a weekend retreat, the possibilities are endless. Conveniently located in Newburg with shopping and dining options close by. You have the town of La Plata 15 minutes north and King George, VA 15 minutes south, via the new Harry Nice Bridge.

12505 Potomac View Dr, Newburg

Listing courtesy of CENTURY 21 New Millennium. Contact:

1241 Johnson Dr, Shady Side
$699,000
3 Beds ⋅ 3 Baths
***OPEN HOUSE SAT 9/12 11am-1pm***Welcome to the Honey Hole of the South Creek! New roof & gutters freshly installed! Welcome to your own private waterfront retreat nestled at the peaceful head of South Creek, where breathtaking views, abundant wildlife, and the ultimate Chesapeake Bay lifestyle come together. Perfectly positioned on a beautifully level lot, this exceptional property offers a private pier ideal for launching a kayak, canoe, paddleboard, or boat, while the nearby community marina provides access to deep-water slips for larger vessels. Residents also enjoy access to the community beach, making every day feel like a vacation. An added bonus is the inclusion of the adjacent Lots 17 & 18 (4907 Thomas Drive), providing additional privacy, flexibility, and future possibilities. Step inside to discover a bright, open floor plan designed to maximize both the water views and natural light. The spacious kitchen features a center island, ample cabinetry, and a sunny breakfast area highlighted by a large picture window overlooking the creek—an unforgettable place to enjoy your morning coffee. The adjoining living room offers the warmth and charm of a wood-burning stove along with sliding glass doors leading to the expansive wraparound screened porch, creating the perfect space for indoor-outdoor entertaining or simply relaxing while watching osprey, herons, and other local wildlife. Large pantry area for additional storage and separate dining room for additional room to spread out. Upstairs, all three bedrooms are thoughtfully situated, including a spacious primary suite that serves as a true waterfront sanctuary. Wake up each morning to panoramic water views from your private balcony, then unwind in the en-suite bath featuring a walk-in closet and plenty of room to recharge after a day on the water. The additional bedrooms are generously sized, with one also enjoying beautiful water views, and are served by a second full bathroom on the upper level. This home has been thoughtfully updated for peace of mind and long-term enjoyment. It may say it was built in 1941, but this home went through an extensive remodel in 1991 taking the original beach bungalow to the oversized colonial it is today. Recent improvements include a brand-new roof (2026), renovated Tigerwood deck, and a professionally encapsulated crawlspace complete with a dehumidification system. If you’ve been dreaming of a waterfront lifestyle that combines privacy, natural beauty, and everyday comfort, this is a rare opportunity to own a special piece of Southern Anne Arundel County. Whether you’re boating, crabbing, kayaking, entertaining on the screened porch, or simply enjoying the peaceful creek views, you’ll quickly understand why this location is so special.

1241 Johnson Dr, Shady Side

Listing courtesy of RE/MAX One. Contact:

3956 Honeysuckle Dr, Edgewater
$2,197,500
4 Beds ⋅ 4 Baths
This remarkable 2+ acre waterfront estate spans two lots with separate tax IDs, offering 560 feet of protected shoreline and stunning 180-degree views over Ramsey Bay to the South River. Surrounded by natural beauty and privacy, the shoreline is reinforced with underwater riprap for lasting stability. The 3,500-square-foot home includes 4 bedrooms, 3.5 baths, rich hardwood floors, a striking stone fireplace, and a gourmet kitchen with high-end finishes. The owner’s suite boasts sweeping water views, while the outdoor spaces feature two spacious waterfront decks and a deep-water private pier with boat lift—ideal for enjoying the Chesapeake lifestyle. An exceptional property not to be missed.

3956 Honeysuckle Dr, Edgewater

Listing courtesy of Curtis Real Estate Company. Contact:

5757 Dockside Ln, Marion Station
$699,500
4 Beds ⋅ 3 Baths
Escape to Maryland's Eastern Shore – Your Private Waterfront Retreat- Wake Up Each Morning to peaceful water views, spend your afternoons boating or kayaking on scenic Coulbourne Creek, and end your evenings watching spectacular sunsets from your deck or second-story balcony. Whether you're searching for a luxury second home, a waterfront vacation retreat, or an investment property with vacation rental potential, 5757 Dockside Lane, Marion Station, Maryland offers the Eastern Shore lifestyle you've been dreaming of. Built in 1971 and completely remodelled by the current owners in 2025, this move-in-ready waterfront home features 4 bedrooms and 2½ bathrooms. The thoughtfully designed floor plan includes 4 bedrooms, 1 full bathroom, and a half bath on the main level, making everyday living convenient while providing excellent accommodation for owners and guests. Upstairs are 2 additional bedrooms and a full bathroom, offering privacy for family, friends, or vacation renters. Nestled on 2.21 private acres, the property provides the perfect blend of waterfront beauty and seclusion. A decorative privacy fence surrounds the inviting inground swimming pool, creating your own private resort where you can spend sunny afternoons swimming, entertaining, or simply relaxing after a day on the water. Outdoor living is at the heart of this exceptional property. The spacious deck overlooking Coulbourne Creek is ideal for outdoor dining, entertaining, or enjoying the peaceful waterfront setting. The second-floor balcony offers another spectacular vantage point for watching wildlife, enjoying your morning coffee, or taking in breathtaking sunsets over the creek, or relax with your nightcap after a tiring day. Boating enthusiasts will appreciate that a permit for a new dock is already in place and may be transferred to the buyer, making it easier to begin enjoying life on the water. The previous dock offered approximately 4 feet of water at the dock with an approximately 7-foot-deep channel, providing protected water for many recreational boats. From your backyard, spend the day cruising Colbourne Creek, fishing, crabbing, kayaking, paddleboarding, canoeing, or exploring the countless creeks and coves that make Maryland's Eastern Shore such a treasured destination. This area is renowned for its outstanding recreational opportunities. Enjoy world-class fishing and crabbing, waterfowl and wildlife viewing, birdwatching, boating excursions, waterfront dining, local marinas, and charming historic towns. Whether you're looking for a quiet weekend escape or an active waterfront lifestyle, you'll discover the relaxed pace and natural beauty that continues to attract second-home buyers and vacationers year after year. The property also offers exciting future possibilities. Subject to all required permits and Planning and Zoning approval, a second dwelling may be constructed on the property, making it ideal for a guest house, multigenerational living, or additional vacation rental income. The property may not be subdivided, and buyers should verify all building requirements with Somerset County Planning and Zoning based on their proposed plans along with any other governmental agencies requiring approval. Whether you envision family gatherings by the pool, weekends on the water, evenings around the fire pit, or creating an exceptional vacation rental, 5757 Dockside Lane offers a rare opportunity to own a beautifully updated waterfront retreat where every day feels like a getaway.

5757 Dockside Ln, Marion Station

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

14265 Melody Dr, Princess Anne
$1,760,000
6 Beds ⋅ 4 Baths
Palatial High-Elevation 5-Acre Waterfront Estate: 5,600 SF All-Brick Rancher with In-Law Suite Please view the Fly-Through Video! Sprawling across five acres of high-elevation land along Wicomico Creek, this magnificent 5,600-square-foot, single-level all-brick rancher delivers an elite waterfront lifestyle. A long, stately driveway draws you past a perfectly manicured lawn and professionally landscaped grounds, creating a dramatic sense of arrival and absolute coastal privacy. The estate boasts premium proximity to the prestigious Wicomico Yacht Club and the scenic vineyards of Bordeleau Winery, offering an incredible maritime backdrop. Masterfully designed for the ultimate boating lifestyle, the waterfront features a private deep-water dock equipped with two boat slips. This setup provides effortless, unrestricted deep-water access, making it easy to cruise straight into the Wicomico River and out to the Chesapeake Bay and beyond! Complementing the maritime design is a massive four-car attached garage, providing abundant space for vehicle collections, water toys, and winter marine storage. Inside, the grand tour begins in the large, cathedral foyer, the true heart of the home. This dramatic entryway showcases custom floor tile, stately columns, and a magnificent Schonbek crystal chandelier that casts a brilliant glow over the entrance. From this central point, the home flows effortlessly into main living spaces where elegant tray ceilings add architectural depth. Soaring walls of glass frame breathtaking, panoramic water views from your high-elevation vantage point, while two cozy gas fireplaces add warmth and elegant focal points to these grand spaces. The culinary core features two separate, custom Quaker Made gourmet kitchens outfitted with high-end appliances, making this property unmatched for hosting grand gatherings. The single-story layout showcases six spacious bedrooms and 3.5 bathrooms, cleverly divided into two distinct wings. A beautiful, architecturally integrated breezeway separates the two living quarters, offering a peaceful, private transition into the fully independent in-law suite, which utilizes the second Quaker Made kitchen. This rare combination of acreage, high elevation, custom design, and premier deep-water dock access represents a once-in-a-generation opportunity. Located just a few hours from the DC and Baltimore metro areas and an hour from Ocean City and Assateague and other area attractions! Extensive Features Document available. Schedule a private tour of this fabulous estate today!

14265 Melody Dr, Princess Anne

Listing courtesy of Coldwell Banker Realty. Contact:

607 Bayshore Ct Unit 2, Ocean City
$459,900
2 Beds ⋅ 3 Baths
Discover a rare and unique opportunity to own a beach property in an exclusive, zero-rental condominium community. Enjoy total peace of mind and live the true coastal lifestyle—whether as a full-time resident or for your personal vacation getaway—completely free from the hassle of renters next door. This beautiful, turn-key unit features a private boat slip right outside your back door, putting you out on the bay in a matter of seconds. The property comes fully furnished and beautifully appointed, highlighted by a cozy wood-burning fireplace and a large, comfortable sectional sofa. The gourmet kitchen is a chef's dream, showcasing expansive granite countertops and premium stainless steel appliances designed perfectly for your summer entertaining! Sip your morning coffee or have your sunset cocktail on your second floor balcony over looking the canal! All this and conveniently located close to some of Ocean City's most beloved restaurants, bars, the beach and Jolly Rogers amusement park!

607 Bayshore Ct Unit 2, Ocean City

Listing courtesy of Sheppard Realty Inc. Contact:

126 Gilbert Ct, Edgewater
$2,700,000
7 Beds ⋅ 5 Baths
Seller says BRING ALL OFFERS! Come Take a look at this One Of A Kind property in the heart of the it All! Grab a Large Plot of Waterfront Land in Annapolis/Edgewater area! Incredible value on this newly updated 10.77-acre waterfront estate, with Picturesque Winter Water views, perfectly nestled on its own private peninsula on Beards Creek in Scotts Cove. Offering over 7,700 sq ft of finished living space, this unique 7-BR, 5-BA home is surrounded by 9.12 acres of wooded conservation easement, delivering extraordinary privacy with no HOA and flexible R-2 zoning.The expansive, versatile floor plan is optimized for multi-generational living or a high-yielding short-term rental—ideal for Navy families and students. Separate living zones include a main-floor bedroom with a full bath and a private side entrance, plus a flexible bonus wing (previously a media room/office) leading to a massive private deck.Premium Spring 2026 updates feature new CertainTeed Cedar Impressions siding in Coastal Grey, fresh Behr Cotton White interior paint, updated deck railings, and new sod/landscaping. Move-in ready with high-end mechanicals: private elevator (2022), 4 geothermal heat pumps (5 zones), tankless water heater, 3 steam showers, whole-house generator, and owned solar panels.Waterfront amenities include 665 ft of creek frontage, a private pier, and 2 boat lifts—perfect for kayaks and smaller watercraft. Unbeatable, secluded location just off Route 2 South with quick access to shopping, dining, Lee Airport, Route 50, Route 97, Annapolis, BWI, and Washington, D.C!

126 Gilbert Ct, Edgewater

Listing courtesy of Coldwell Banker Realty. Contact:

1011 Lillies Ln, Ellicott City
$710,000
3 Beds ⋅ 4 Baths
***OELLA*** ***HOME WARRANTY INCLUDED*** Spacious, freshly painted townhouse overlooking picturesque Patapsco River! Three sun-soaked, above-ground levels located in the Dickey Ridge community of sought-after OELLA with three bedrooms, two full bathrooms on the Upper Level, a half bath on both the Main Level and Lower Level, office space on two levels, and tons of storage with a Lower Level Bonus Room and a garage that is over 400 square feet. Outdoor spaces include a welcoming front porch, expansive back patio, and the beautiful front balcony with year-round water views. Recent UPGRADES include NEW 4" red oak hardwood floors on the Upper Level (2024), washing machine (2024), insulation (2025), conversion to LED recessed lighting (2025), new shower door in Primary Bath (2026), and gutters (2026). Large gourmet Kitchen with tons of cabinetry, counter space, deep pantry, and room for eating in opens up to Dining Room with room for a sizable table and Living Room perfect for quiet nights by the wood-burning fireplace or for entertaining large parties. Primary Bedroom with vaulted ceiling, attached luxury bathroom with dual vanities, soaking tub, and walk-in shower, substantial walk-in closet, and plenty of room for end tables, dressers, and more. Less than 0.5 miles from historic downtown Ellicott City dining, shopping, and museums, this home offers you the ability to live the quaint lifestyle without giving up the space and convenience of a modern townhouse.

1011 Lillies Ln, Ellicott City

Listing courtesy of Pearson Smith Realty, LLC. Contact:

12555 Coopers Ln, Worton
$1,395,000
4 Beds ⋅ 3 Baths
Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with gleaming hardwood floors and huge sliders looking onto the deck and Still Pond Creek. 2 woodburning fireplaces. Updated kitchen with high-end stainless steel appliances. Laundry room off the kitchen. Steps down to your private waterfront oasis and dock. The lower level features a large family room, 2 bedrooms, a full bath and plenty of storage. This home has that unmistakable Eastern Shore feel. You won't want to miss this spectacular property.

12555 Coopers Ln, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

2 48th St Unit 1402, Ocean City
$1,275,000
3 Beds ⋅ 3 Baths
Experience the most breathtaking views of the ocean, bay, and city skyline from this spectacular 14th-floor condominium in The Gateway Grand, Ocean City’s premier luxury residence. From sunrise over the ocean to sunsets over the bay and the sparkling city lights at night, the views are endless and unforgettable. This 3-bedroom, 3-bath floor plan allows for the master bedroom to access the incredible vistas. This residence is offered fully furnished and equipped, and includes a strong rental history—making it ideal as a vacation home or investment property. The gourmet kitchen features granite countertops, upgraded cabinetry, beautiful tile flooring, and stainless steel appliances. Elegant finishes and an open floor plan create a seamless blend of comfort and sophistication. Residents of The Gateway Grand enjoy world-class amenities, including: Year-round heated indoor pool and a large heated outdoor pool, 24-hour fitness center, kids club room, Large Oceanfront sundeck , Two reserved parking spaces and a large deeded storage locker, Secure building access with a staffed front desk, evening security, and camera monitoring of all amenities and the parking garage. This luxurious condo perfectly combines coastal living with resort-style comfort—offering both tranquility and convenience in one of Ocean City’s most sought-after locations.

2 48th St Unit 1402, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

5209 Al Jones Dr, Shady Side
$149,900
WATERFRONT OPPORTUNITY!! Discover the perfect setting to build your dream home or weekend retreat on this waterfront lot offering breathtaking views of the Chesapeake Bay. Nestled in the quiet, secluded community of Columbia Beach, this approximately 4,450-square-foot homesite is already serviced by public sewer, making it an exceptional opportunity to bring your vision to life. Wake up to stunning sunrises, enjoy the peaceful waterfront surroundings, and embrace the laid-back Chesapeake lifestyle with boating, fishing, kayaking, and endless opportunities to relax by the water. Whether you're looking to create a full-time residence or a private coastal escape, this rare waterfront property offers the chance to own a slice of the Bay in a tranquil setting. Don't miss this unique opportunity!

5209 Al Jones Dr, Shady Side

Listing courtesy of CENTURY 21 New Millennium. Contact:

512 Robin Dr Unit 3, Ocean City
$269,900
1 Beds ⋅ 1 Baths
Possibility of purchasing slip #10 from a neighbor if a boat slip a requirement! Adorable waterfront 1-bedroom 1-bath condo located bayside in Ocean City, MD! No need to worry about climbing steps, just park and immediately enter into your ground floor residence. Upon arrival you will appreciate the care the current owners took to upgrade and maintain this property. The first thing you will note is the uniform luxury vinyl plank flooring throughout the condo that allows for easy care at the beach! Continue through the bedroom into the bathroom to see upgrades including a new vanity, light fixture, and crab wallpaper that remind you that you are at the beach in Maryland! Back outside of the bathroom the remodeled kitchen will stop you in your tracks. From the stainless-steel appliances to the quartz countertops to the ceramic tile backsplash and the quality soft close cabinets and drawers, you will be impressed! Finally, circle back to the view you saw as soon as you opened the front door, a wide canal sparkling from the sun's rays. The sound of lapping water can be heard from the spacious living by leaving the quality vinyl slider open that also has built in blinds for privacy when needed. The living room features a pull-out sofa with extra comfortable mattress for guests. In addition to one parking spot on the surface lot the condo also has an assigned storage locker on the ground floor for beach items. Make sure to add this condo to your list to see!

512 Robin Dr Unit 3, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact:

106 Edward Taylor Dr Unit 208 B, Ocean City
$45,500
2 Beds ⋅ 2 Baths
You know you want a piece of the American dream... a condo in Ocean City * Here is your opportunity to make your dream come true * Look at this... 2 Bedroom 2 Bath Condo on the Canal * Included in the quarterly maintenance fee All utilities, property taxes and maintenance * So you have no reason not to jump on this opportunity * Yes you can rent your week(s) * Completely furnished * Full kitchen * Sunsets * Quick strolls to the beach, shopping, restaurants, busline * Oh yes, there is a community pool too * Call me today to schedule a showing *

106 Edward Taylor Dr Unit 208 B, Ocean City

Listing courtesy of Sea Grace @ North Beach Realtors. Contact:

Schumaker Woods Circle, Salisbury
$129,900
Prime waterfront lot overlooking Schumaker Pond. Owner is currently stepping through site plan approvals so that all can be ready for your new home. Public water & sewer is available.

Schumaker Woods Circle, Salisbury

Listing courtesy of ERA Martin Associates. Contact:

7737 Patuxent Dr, Saint Leonard
$1,245,000
4 Beds ⋅ 4 Baths
Experience exceptional waterfront living on the beautiful Patuxent River! This stunning ranch-style home offers over 3,300 square feet of thoughtfully designed living space with 4 bedrooms, 4 full bathrooms, and 50 feet of private river frontage complete with a private pier and charming crab shack. Designed for both everyday living and entertaining, the gourmet kitchen features stainless steel appliances, a six-burner commercial-grade range, a butler's pantry, and an open-concept layout that flows seamlessly into the dining area and spacious family room. Elegant shiplap accents, exposed beams, crown molding, and expansive windows frame breathtaking views of the Patuxent River, creating a warm and inviting atmosphere. The main level also features a private in-law suite offering two bedrooms, a full bathroom, a walk-in closet, and laundry room—an ideal setup for multigenerational living, extended family, guests, or a private home office. The luxurious waterfront primary suite, located on the lower level, is a private retreat offering panoramic river views, an oversized walk-in closet, and a cozy gas fireplace. The spa-inspired primary bath features heated floors, a relaxing jetted soaking tub, and luxurious finishes designed for ultimate comfort. Step outside and embrace the waterfront lifestyle. Spend your days boating, fishing, crabbing, or kayaking from your private pier, then unwind in the hot tub or entertain family and friends on the expansive deck while taking in spectacular sunsets. The authentic crab shack adds the perfect touch for enjoying fresh catches and making unforgettable waterfront memories. This exceptional property offers the perfect blend of luxury, comfort, and the unmatched beauty of Chesapeake Bay waterfront living. A rare opportunity to own a private riverfront retreat where every day feels like a vacation.

7737 Patuxent Dr, Saint Leonard

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

23 Mallard Dr E, Ocean Pines
$2,323,000
5 Beds ⋅ 6 Baths
23 SPECIAL! SCHEDULE A TOUR TODAY!! Welcome to one of Ocean Pines’ most extraordinary waterfront estates, where luxury, recreation, and coastal living come together in a truly one-of-a-kind offering. Situated on a beautifully positioned waterfront homesite with 75 feet of newly bulkheaded shoreline, this remarkable residence encompasses approximately 9,200 square feet of thoughtfully designed living space with 5 bedrooms, 5.5+ baths, and an unmatched collection of resort-style amenities. Designed for entertaining on every level, the home features a spectacular 63-foot indoor pool with a 7-foot depth, private locker room, movie theater, expansive game room with wet bar, sunroom, and an oversized chef’s kitchen that opens seamlessly into light-filled living and dining spaces framed by soaring ceilings and walls of glass overlooking the water. The outdoor living experience is equally impressive. Enjoy expansive waterfront decking, an enclosed brick courtyard with a charcoal grill, multiple spaces for gathering, a rooftop observation deck with panoramic views, and direct boating access from your private dock featuring an 8,000-pound boat lift. Whether hosting family and friends or enjoying a quiet evening overlooking the water, every space has been designed to embrace the coastal lifestyle. Additional highlights include a two-car garage, generous driveway and guest parking, and the home is offered fully furnished (with select exclusions), allowing you to begin enjoying it from day one. Properties of this caliber are exceptionally rare. Whether you’re searching for an extraordinary primary residence, an unforgettable coastal retreat or the ultimate waterfront investment property, 23 Mallard Drive East delivers a lifestyle few properties can match. Schedule your private showing today and discover what life on the water was meant to be!

23 Mallard Dr E, Ocean Pines

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact:

12623 Sheffield Rd, Ocean City
$817,500
3 Beds ⋅ 2 Baths
Live the ultimate West Ocean City waterfront lifestyle in the highly sought-after Cape Isle of Wight community. Situated on an oversized waterfront lot with approximately 80 feet of bulkheaded canal frontage, multiple deeded boat slips, and panoramic bay and canal views, this exceptional property offers quick navigable access to Assawoman Bay, making it a dream for boaters, anglers, and outdoor enthusiasts. Step from your backyard onto your boat for a day of fishing, cruising to waterfront restaurants, exploring the Ocean City Inlet, or relaxing at nearby sandbars, then unwind with breathtaking sunsets from the covered porch or second-level balcony. Inside, this inviting coastal retreat features 3 spacious bedrooms, 2 full bathrooms, an open-concept floor plan, beautiful wood flooring, an updated kitchen with upgraded countertops and modern finishes, and large windows showcasing incredible water views. Recent and notable improvements add to the home's appeal, including an HVAC/heating system approximately 5 years old, a hot water heater approximately 9 years old, and solar panels installed in November 2021. The deck is approximately 10 years old, and the boat dock has been enhanced with new decking, providing a refreshed space to enjoy the waterfront and easy access to your boats and watercraft. Designed for waterfront living, the property also offers an attached two-car garage and a detached garage/carriage house ideal for a workshop, studio, hobby space, or additional storage. There's plenty of room for boats, jet skis, kayaks, paddleboards, golf carts, beach gear, and fishing equipment, plus an outdoor shower, oversized yard, and generous outdoor entertaining space. Just minutes from Ocean City's beaches, Boardwalk, marinas, waterfront dining, shopping, championship golf courses, and Assateague Island, this home offers the perfect balance of peaceful waterfront living and convenient access to the best of Maryland's Eastern Shore. Whether you're looking for a primary residence, vacation home, or weekend getaway, this is a rare opportunity to own one of West Ocean City's premier waterfront properties.

12623 Sheffield Rd, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact:

43410 Old Wharf Ln, Hollywood
$1,299,000
4 Beds ⋅ 3 Baths
Nestled on the shores of the Patuxent River is this very private, custom-built, all brick home. Beautiful hardwood flooring throughout, modern kitchen and baths, a family room with fireplace and built-ins all situated on 5 sprawling acres. The property boasts 402 feet of riprapped shoreline. Old growth trees grace the circular driveway. The grounds have been professionally landscaped with a sprinkler system installed. For the outdoorsman, there is a 4 stall horse barn, an enclosed dog run and more. Enjoy nature's beauty on the water; conveniently located in North Hollywood for a D.C. commute. A great get-away for enjoying peace and tranquility in the Country.

43410 Old Wharf Ln, Hollywood

Listing courtesy of KW Metro Center. Contact:

2200 Poplar Rd, Baltimore
$465,000
2 Beds ⋅ 1 Baths
LAUNCH YOUR KAYAKS FROM WATER'S EDGE AND ENJOY THE NATURAL BEAUTY OF LANDSCPE. OWNER SAID "MAKE ALL OFFERS, MOTIVATED" Owner will Subordinate an Improvement, Such as a New Pier or 2nd Story Addition, Private Finaning. Perfect live here year round, and enjoy all the natural beauty of living on the water on Sue Creek. Take time to relax on the deck and watch the Sunsets directly in front. You'll want to stay forever, perhaps take a boatride or row in the calm water. Great home with new CherryWood kitchen, plenty of cabinet space. Nice dining area, with view to the waterfront. Living room with hardwood floors, and access to the waterfront side. New Sunroom Addition Trex Deck. Entrance Area, New Hearth & Stone, Wood Stove, Front Stoop, replaced cap metal rail of new wood railing. Fully open Basement level has been improved office space, painted concete floor, Added Insulation in Joist for Energy Efficiency, Added Electrical Service New Disconnet & Feed Panel 2025, Added FIOS internet. with space for office with built in shelving, and cabinet space. Outside, you'll find the natural secluded deck, with views to the sandy shore, and a walkway, to the water, Launch your Jet Ski, or john boat. Structure of home: Solid 8" Masonry walls to roof peak. Applied insulation and vinyl siding to exterior. Stainless appliances. Existing 80' PIER needs work. Can be replaced, with County Permits as it is " Grandfathered" existing 80 pier. Very Important to know, you'll always be able to rebuild Pier. AC unit: Forced-air system; independent duct work from heating system. Located in roof eaves. Electrical: New service upgrade February 2026. 150 AMP with surge protection added. Close to all major waterfront restaurants, Charleys marina & tiki bar, LunaSea, the Middle River Yacht club, Carsons' Creek seafood restaurant. 10 minutes from Middle River. Easy care home, lots of mature plants and trees, landscaping done by Owner.

2200 Poplar Rd, Baltimore

Listing courtesy of RE/MAX Advantage Realty. Contact:

1713 Doeller Rd, Fishing Creek
$2,950,000
5 Beds ⋅ 6 Baths
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact:

104 Myrtle St, Oxford
$1,399,000
3 Beds ⋅ 3 Baths
Major Price Improvement! Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for enjoying life on the water. Fabulous gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 + feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Sold As Is

104 Myrtle St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact:

00 Westernport Rd Sw, Westernport
$339,000
Discover the endless possibilities with this exceptional 30± acre riverfront property offering a rare combination of natural beauty and investment potential. Zoned for agricultural and commercial use, this versatile tract features a blend of level, cleared land ready for immediate use and wooded acreage that provides privacy, recreation, and scenic appeal. With beautiful river frontage and easy access, this property is ideal for farming, a business venture, a campground or RV park, event venue, recreational retreat, or your future dream home (subject to local regulations). Whether you're looking to expand your agricultural operation, develop a commercial enterprise, or invest in a one-of-a-kind piece of land, this property offers the flexibility and space to bring your vision to life. Don't miss this unique opportunity to own a beautiful stretch of riverfront acreage with unlimited potential!

00 Westernport Rd Sw, Westernport

Listing courtesy of Coldwell Banker Home Town Realty. Contact:

23145 Edelen Webster Rd, Deal Island
$965,000
A truly rare opportunity to own 9.63 secluded Bayfront acres overlooking the breathtaking Tangier Sound and the Chesapeake Bay. This extraordinary property offers approximately 500 feet plus of shoreline, reinforced and protected with stone riprap, along with a private sandy beach—an exceptional feature for this Eastern Shore gem. Enjoy spectacular, postcard-worthy sunsets and panoramic views across the pristine coastal waters, where endless horizons create an unforgettable backdrop every day. The property includes an existing old home (no Value), several old outbuildings, and a 100-foot pier that pier requires rebuilding, the existing pilings appear to be in serviceable condition, providing an excellent foundation for restoring your private waterfront access. Comprised of five contiguous parcels with excellent road frontage and private gated driveway. This unique estate offers exceptional privacy, flexibility, and future potential. The surrounding waters are renowned for outstanding recreational opportunities, including abundant Chesapeake Bay blue crabs, striped bass (rockfish), fishing, boating, kayaking, and waterfowl. Whether you envision building a private family retreat, an estate property, or preserving an unmatched waterfront sanctuary, this offering represents a unique opportunities available on Maryland’s Eastern Shore. Properties of this size, privacy, and waterfront quality seldom become available. Experience the beauty, tranquility, and endless possibilities this remarkable bayfront property has to offer.

23145 Edelen Webster Rd, Deal Island

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC. Contact:

7680 Country Club Ln, Chestertown
$825,000
5 Beds ⋅ 4 Baths
Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

300 Woods Point Rd, Chester
$2,625,000
3 Beds ⋅ 2 Baths
Privacy without isolation! - Rare Find - 2 comfy homes on one waterfront property, each served by public sewer.! Both with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod recently updated in spring 2026 ( 3-bedrooms, 2-bathrooms, with enclosed and screened porches.) The former detached garage converted into a 2 story guest cottage (2BR, 1.5 BA) has a fabulous screened porch you'll spend endless hours on. A separate building provides versatile storage for equipment or hobbies. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors in most rooms. Upgraded countertops and new appliances elevate the kitchen, convenient to the screened porch perfect for gatherings. The living room, complete with a brick fireplace, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom, or home office, in this traditional floor plan that flows seamlessly throughout. The exterior amenities are equally impressive, featuring a private shoreline and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. . The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or gardens.. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

328 Oakdale Rd, Pasadena
$820,000
3 Beds ⋅ 2 Baths
EXCEPTIONAL 2014 Custom Built Waterfront property in Pasadena now offered $10k below appraisal!! at $820k!! Solid energy efficient construction, oversized 2-car garage for the car enthusiast or home based business, lots of storage, designer features throughout, the utmost in waterfront lifestyle including an in-ground pool, no HOA, super convenient to 100/97/2 NSA/Ft. Meade areas! With thoughtful planning and design, this home features ICF construction (see attached info sheet - providing extreme Energy Efficiency, Noise Reduction, Safety & Durability), Secure Entryways, cozy open space layout with beautiful views of the Magothy River, excellent flow to outdoor living areas and two primary bedroom suites! From the moment you step under the pergola onto the stone patio feel this home welcoming you, hear the sound of the river calling, see the light reflecting in the refreshing waterfront in-ground pool THIS, this is home! Entering from the enclosed portico into the foyer notice the quality craftsmanship, exposed beams, designer colors, perfect lighting, tall ceilings, expert attention to detail. The gourmet kitchen is designed with daily life and entertaining in mind complete with solid surface counters, soapstone sink, range, pantry, wall oven, built-in microwave, mini-fridge for drinks. Notice the little extras like the copper prep sink w/Instant Hot water faucet, a convenient magnetic knife holder, the authentic port window and stunning hickory island cabinets. Enjoy meals with a water view and cozy evenings around the wood stove. You will LOVE the big fully screened deck (nice try mosquitos!) complete with ceiling fan/lights and an outdoor kitchen area (propane stove as-is) or consider converting this into a 4 season family room for another living space! The balcony offers another perfect spot to relax and enjoy the peaceful views. The lower level primary suite features a media room (OR easily convert to a 3rd bedroom), a light filled sitting room that walks out onto a covered private stone patio, the spacious bedroom has barn doors, a 6x12 walk-in closet w/built-ins and dressing area. The spa bathroom has a jetted soaking tub, walk-in shower, vanity and features heated floors! Conveniently located is the laundry and entrance to a secure storage/utility room including a heat pump water heater for added efficiency, generous storage area, and safe. This home also has a whole house fan; they thought of everything! A side entrance into the mudroom and lower level suite has a handy sink and additional storage. The spacious upper level bedroom has tall ceilings, perfect natural light, a double closet and connects to a full bathroom. Tucked out of sight is a perfect office nook with custom built-in shelving. This property has it all for the outdoor water enthusiast with a .60 acre lot, rare waterfront level space (garden or volleyball?!) a 6' wide private pier complete with party platform and 10k lb boat lift, kayak launch, and the convenience of water & electric at three critical spots! Finished with the river for the day? Cool off in your own private, refreshing waterside in-ground pool (as-is) outfitted with FROG mineral system filtration. The rambling backyard is fully fenced (reinforced to keep pets in and critters out!) Restore the charming 1932 fish pond to add to the charm and magic of this one of a kind property. Mature landscaping and fruit trees are a delight! The oversized 2 car garage features separate 220-volt electric, a lower level walkout storage room, front entry and a convenient side door leading to the gorgeous stone patio shaded by a custom built pergola - a stunning entryway to this spectacular home! Chesapeake schools. Super convenient to Rt 100/97 BWI/NSA. There is so much more to this house, be sure to check out the Features Sheet and contact us to schedule your private showing today! Ideally situated at the end of a no-thru street, fortunate will be one to call this gem home!

328 Oakdale Rd, Pasadena

Listing courtesy of Douglas Realty LLC. Contact:

2404 And 2407 Hoopers Island Rd, Fishing Creek
$575,000
3 Beds ⋅ 2 Baths
Escape to the unspoiled beauty of Hoopers Island, where peaceful waterfront living and world-class fishing, crabbing, and boating are part of everyday life. Situated on a beautifully landscaped 1.06-acre corner lot, this charming 3-bedroom, 2-bath home offers the ideal Eastern Shore retreat with generous indoor and outdoor spaces designed for gathering with family and friends. The heart of the home is a beautifully appointed kitchen featuring granite countertops, abundant cabinetry with under-cabinet lighting, a center island, double wall ovens, gas cooktop, wet bar, and custom wood ceilings. Original pocket doors, warm wood accents, and pellet stoves add timeless character throughout, while the spacious sunroom with skylights and a stone hearth creates a cozy place to unwind year-round. Upstairs offers three bedrooms, a full bath, and a loft that comfortably accommodates additional guests, making this an ideal full-time residence or weekend getaway. Two storage sheds provide ample space for boating and outdoor equipment. Included in the sale is a rare additional 0.13-acre Commercial Maritime waterfront parcel featuring a 100-foot pier with approximately 5 feet of water depth, multiple boat slips, and endless opportunities to enjoy the Chesapeake Bay lifestyle. Whether your passion is offshore fishing, crabbing, kayaking, or simply watching the sunset over the water, this property is ready for your next adventure. Owners also have a duck blind permit with site right off the property for hunter enthusiasts. What more could you ask for? Located just minutes from local favorites including Old Salty's Restaurant, Hoopers Island General Store, and Madhouse Oysters, this exceptional offering combines authentic Eastern Shore charm with the waterfront lifestyle so many dream of—but few ever find.

2404 And 2407 Hoopers Island Rd, Fishing Creek

Listing courtesy of Sharon Real Estate P.C.. Contact:

193 Red Run Rd Unit 1-B-3, Oakland
$550,000
2 Beds ⋅ 2 Baths
Ultimate lakefront living awaits at Red Run! This stunning 2-3BR, 2BA condo features a second-floor loft and a versatile den easily used as a 3rd bedroom. Enjoy breathtaking lake views from your gorgeous primary suite and private lakeside balcony. Extensively upgraded with a extensively upgraded kitchen boasting granite countertops and soft-close cabinetry, a newly remodeled laundry room with a new water heater and sink, an upgraded electrical panel, and premium cement-backed luxury vinyl plank flooring for ultimate durability. Stunning new shiplap ceilings with recessed lighting illuminate the freshly painted main living spaces, complete with a cozy wood-burning fireplace. Includes an assigned deep-water boat slip, outdoor storage, and access to 11 acres of incredible amenities: a heated pool, tennis courts, playground, kayak racks, and a stone fire pit. Major community updates include a new metal roof and resurfaced courts. Just minutes from downtown Oakland, Garret Cinemas, and shopping! Seller will sell his 2011 Sea Ray 195 with 4.2 L EFI engine for $4500.00 OBO "As=Is " see photos and dock slip

193 Red Run Rd Unit 1-B-3, Oakland

Listing courtesy of RE/MAX Results. Contact:

5229 Heron Rd, Cambridge
$50,000
Build your dream home on this scenic 3.53-acre wooded lot in the exclusive Heron Harbor community, nestled along Webbs Creek, which feeds into the Choptank River. Surrounded by water and nature, this peaceful setting offers access to a community pier on navigable water—perfect for kayaking, boating, and enjoying fresh Eastern Shore crabs. HOA fees include dock maintenance and BIP septic hook-up access. With easy access to downtown Cambridge, shopping, restaurants, and more, you’ll enjoy the perfect balance of convenience and seclusion. Embrace the best of Eastern Shore living in this quiet, water-oriented community.

5229 Heron Rd, Cambridge

Listing courtesy of Northrop Realty. Contact:

140 Spa Dr, Annapolis
$4,600,000
5 Beds ⋅ 4 Baths
An extraordinary opportunity to own one of Annapolis’ most distinctive waterfront properties, offering some of the finest views on Spa Creek and the rare privilege of owning your own private marina in your backyard with dockside parking. Perfectly positioned to capture breathtaking panoramic vistas, this elegant Nantucket-inspired residence is filled with natural light, featuring walls of glass that showcase the ever-changing waterfront from nearly every room. Multiple balconies and an expansive waterside terrace invite effortless indoor-outdoor living, creating exceptional spaces for entertaining or simply enjoying the beauty of life on the water. A dockside workshop is a great opportunity to work and enjoy waterfront living. The thoughtfully designed floor plan includes spacious living areas, a versatile 1800 square feet (approximate) lower level with an in-law suite or private guest accommodations, and endless opportunities to personalize the home to suit your lifestyle. This home even has a koi pond in the front yard. Whether you’re an avid yachtsman, seeking a multigenerational waterfront retreat, or searching for a truly one-of-a-kind Annapolis property, this exceptional offering combines luxury, privacy, and an unmatched boating lifestyle in one remarkable setting.

140 Spa Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1511 Crocheron Rd, Bishops Head
$319,900
4 Beds ⋅ 2 Baths
WATERFRONT! Calling nature lovers; this is the private Eastern Shore retreat you've been seeking! This potential Airbnb home set in the heart of Maryland's Lower Eastern Shore offers the peace, privacy, and wide-open space that outdoor enthusiasts value most. Surrounded by natural habitat and abundant wildlife, the area is well known for frequent sitka deer sightings and exceptional opportunities to enjoy the outdoors right from your own backyard. Whether you're looking for a hunting retreat, recreational property, or full-time residence with room to roam, this property delivers. The home features 4 bedrooms, a dedicated office, and 2 full bathrooms, along with a remodeled kitchen that serves as the perfect gathering place after a day outdoors. Additional amenities include a spacious floor in attic, a fenced yard with an above-ground pool, a barn with multiple stalls, and a storage shed, and a brand-new generator, providing both convenience and functionality for country living. Located in Toddville, a community known for its rich watermen's heritage, scenic marshlands, and unspoiled landscapes, you'll enjoy easy access to the outdoor lifestyle the Eastern Shore is famous for. Spend your days hunting, fishing, crabbing, boating, kayaking, birdwatching, or simply enjoying the quiet beauty that surrounds you. Whether you're searching for a basecamp for outdoor adventures, a weekend getaway, or a peaceful place to call home, 1511 Crocheron Road offers the space, privacy, and natural setting to make it all possible. (one photo was enhanced with virtual staging to show furniture)

1511 Crocheron Rd, Bishops Head

Listing courtesy of A Squared Realty. Contact:

31923 River Park Rd, Millington
$435,000
3 Beds ⋅ 2 Baths
Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades include all-new appliances (2021), a 12' x 20' shed/workshop (2023), and new HVAC and viny siding (2024). Step outside to a spacious deck overlooking the river and your private dock--perfect for fishing, launching kayaks, or docking a small boat. Conveniently located just 15 minutes from both Chestertown, MD and Middletown, DE, this waterfront retreat offers the ideal blend of comfort, convenience, and outdoor enjoyment. A must-see!

31923 River Park Rd, Millington

Listing courtesy of RE/MAX Chesapeake. Contact:

Madonna Rd, Jarrettsville
$549,900
The property has two building rights and may be subdivided. A contract that is contingent on percolation testing will be considered and can be conducted now versus awaiting wet season. The Seller will not hold the property until after a subdivision plat is approved. The property is eligible for the Harford County AG Land Preservation Easement and other easement programs which could easily put $4,000-$8,000/acre back in your pocket! Most building lots hand you a number on a street and neighbors close enough to wave at. This one hands you twenty private acres, a shared drive of your own, and a pond no one else can see. Take this and build the property of your dreams or use both building rights and start your family compound. These 20.40 secluded acres rest off Madonna Road in northern Harford County, a few minutes from the village of Madonna and the town of Jarrettsville. A private shared driveway that extends off from Norrisville Rd, leaves the main road and winds back through the trees to the quiet heart of the property. This is where you dreams begin. The interior opens to a possible future, homesite with a three-quarter acre pond in the midst of it all while mature woods wrap around all sides, the kind of setting most people only get to rent for a weekend. The pond is the centerpiece of family life here. It holds bass and catfish, so the kids can fish it on a warm summer evening and actually catch something. It is quiet and private enough to jump in and cool off in, when the day runs hot. Picture the back porch light coming on, a campfire by the water, and children with the run of their own woods instead of a fenced backyard. Building here is realistic, not hypothetical. The land carries a history of soil and percolation testing tied to a homesite, the zoning is agricultural, and access reaches the property from both Madonna Road and Norrisville Road, which is Route 23, so you are never depending on a single way in. There is room for the house, a shop or barn, a garden, and still acres of trees left over. The timber is a real mix of tall white pines and mature hardwoods, and because this is the only sizable block of woods in an area of open agricultural fields, it pulls in wildlife. Deer and wild turkey feed in the surrounding crops and then bed and travel through these woods, leaving trails across the property. For a buyer who hunts, this is merely your own little private wildlife preserve out the back door. For everyone else, it is simply the place where all the deer go and stay. Families also buy based on locations for the schools, and this address sits in the North Harford High School area of Harford County Public Schools, the rural northern end of the county known for its small-town feel and strong community. Jarrettsville, Bel Air, and the I-83 corridor are all an easy drive, while Rocks State Park, Deer Creek, and the wineries and gardens of northern Harford County are close enough for a weekend. Build the home you have been picturing on high, dry, private ground. Let the kids grow up with woods to explore and a pond to fish. Hunt the trails in the fall. A secluded homesite of this size, with water, mixed timber, and two ways in, does not come up often in this part of Maryland. All information is deemed reliable but is not guaranteed. Buyers and their agents are encouraged to perform their own due diligence to verify property boundaries, access, and soil and site suitability for their intended plans. We are happy to help connect you with the right local resources as you plan your project.

Madonna Rd, Jarrettsville

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

24 Stacy Ct, Ocean Pines
$1,249,500
4 Beds ⋅ 3 Baths
Waterfront opportunity in sought-after Terns Landing! Welcome to 24 Stacy Court, where stunning canal and bay views take center stage. This spacious waterfront home features 4 bedrooms, 2.5 baths, and an open floor plan designed to maximize natural light and water views from nearly every room. The first floor offers a desirable primary suite with a private full bath, an eat-in kitchen, formal dining area, and a bright sunroom overlooking the water. Upstairs, you'll find three additional bedrooms along with a large bonus room complete with a wet bar, making it the perfect space for entertaining, game nights, or relaxing after a day on the water. Boating enthusiasts will appreciate the private bulkhead, approximately 10 years old, and convenient access to the bay. Recent updates provide added peace of mind, including a new roof (Spring 2026), second-floor HVAC system (September 2026), and a new driveway (Fall 2025). To make this opportunity even more attractive, the seller is offering a one-year home warranty and $10,000 toward closing costs with a reasonable offer. Don't miss your chance to enjoy waterfront living in one of the area's most desirable communities.

24 Stacy Ct, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact:

11639 Sidewinder Ln, Lusby
$349,500
3 Beds ⋅ 2 Baths
Welcome home to your own peaceful lakeside paradise! Nestled along the shoreline of beautiful Lake Lariat, 11639 Sidewinder Lane offers the perfect blend of comfort, charm, and relaxation. This inviting home features 3 bedrooms and 2 bathrooms, along with brand-new kitchen countertops, fresh paint, and new flooring and carpet throughout. Imagine starting your mornings on the deck overlooking the lake with a warm cup of coffee as the sun rises over the water. The spacious back deck provides the ideal setting for outdoor dining, entertaining guests, or simply unwinding while taking in the scenic views. Whether you enjoy kayaking, fishing or relaxing by the water's edge, this property delivers the lakefront lifestyle so many dream of. Whether you enjoy kayaking, fishing, or relaxing by the water’s edge, this property delivers the lakefront lifestyle so many dream of.

11639 Sidewinder Ln, Lusby

Listing courtesy of RE/MAX One. Contact:

40115 Combs Creek Way, Leonardtown
$1,590,000
5 Beds ⋅ 4 Baths
Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare opportunity to own a private waterfront oasis with an expansive shoreline along both Breton Bay and Combs Creek, extending all the way to the point of its sandy beach peninsula. Enhanced riprap protection, extensive landscaping, and mature surroundings create a truly unforgettable setting. Enjoy 1,545 feet of bay-front water life. Kayakers, yachters, dolphin enthusiasts, fishers, crabbers, and star-gazers are just a few who may find interest in this exemplary waterfront gem. The centerpiece of the outdoor living experience is the spectacular saltwater pool, thoughtfully designed for both relaxation and entertaining. The saltwater pool is finished with premium Wet Edge Premier Stone and Artistic Paver tiles, (featuring embedded seashells sourced from Miami). The tanning ledge measures approximately 8x16' providing the perfect place to lounge and enjoy waterfront views, while a diving board adds to the fun. A dedicated pool pump house and separate dual pool storage unit with its own half bath supports the pool operation. Water enthusiasts will appreciate the exceptional marine amenities. Walking down the hill from the residence leads to a private boathouse and pier system designed with serious boaters in mind. The pier features new stringers, updated power and water service, two slips including the boathouse, and one open slip, a fish cleaning station, and kayak launch area. Low water depth at the end of the pier averages approximately eight feet, making this deep-water location highly desirable for larger vessels and year-round boating. The boathouse, along with the pier, pool house, and detached garage, are all serviced through a dedicated electrical panel system. Water is also available on the pier. Inside, the home has undergone substantial improvements over the years, including a complete transformation of the kitchen and dining areas, creating a stunning gourmet gathering space that serves as the heart of the home. Updated Andersen windows, updated flooring, fresh interior paint, and a beautifully finished laundry and utility room further enhance the home’s appeal. The impressive enclosed sunroom, encompassing approximately 440 square feet, offers year-round enjoyment and flexible living space while showcasing the property’s incredible waterfront views in all seasons. Additional improvements include HardiePlank fiber cement siding, a whole-house generator capable of operating the kitchen and well systems during outages, and a detached 2.5-car garage with a raised floor to improve site grading. The garage offers exceptional storage and future potential for additional finished space should a buyer desire to build up. The well is approximately eight years old. When drilled, the well and pump were upgraded to provide for the additional water needs of the pool, pier and future lawn irrigation. The laundry and utility area features a Navien boiler installed in 2016, providing domestic hot water as well as support for the home’s heating systems. For added value and future convenience, the sellers are in the process of connecting the property to public sewer, which is available within the property. We cannot wait for you to come see the lifestyle that Combs Creek Way has to offer you.

40115 Combs Creek Way, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact:

915 Hudson Rd, Cambridge
$410,000
2 Beds ⋅ 1 Baths
Adorable waterfront cottage nestled along the peaceful shores of Hudson Creek., This charming 2-bedroom, 1-bath home features an open-concept kitchen, dining, and living area designed to maximize comfort and showcase beautiful waterfront views and amazing sunsets. Additional features include front and back porches, firepit, fresh paint throughout and a detached storage shed for all your outdoor gear, Experience Eastern Shore waterfront living and spend your days fishing or crabbing from your private pier, launch your kayaks for an afternoon on the creek, or simply unwind on the deck while taking in the spectacular sunsets. This low-maintenance property has been successfully operated as an income generating vacation rental, making it an excellent opportunity as a personal getaway, investment property, or both. The home is being sold fully furnished, including two kayaks, a BBQ grill and deck furniture

915 Hudson Rd, Cambridge

Listing courtesy of TTR Sotheby's International Realty. Contact:

14940 Chesapeake Bay Dr, Scotland
$799,000
4 Beds ⋅ 3 Baths
Two Homes, One price! Imagine waking up each morning to breathtaking, unobstructed views of the Chesapeake Bay. Here, the water isn’t just something you see—it’s part of your everyday life. Relax on your private pier, launch your kayak, cast a fishing line, or simply watch the sun dance across the Bay. A sandy beach has been thoughtfully created, allowing you to enjoy carefree days by the water regardless of the tide. Nature lovers will appreciate watching the resident ospreys return each year to build their nests, hatch their young, and soar above the shoreline—a front-row seat to one of the Chesapeake’s greatest treasures. The charming waterfront A-frame has been enhanced with a beautifully enclosed porch, creating the perfect space to gather with family and friends for steamed crabs, oysters, and unforgettable waterfront dinners in every season. Expansive decking on the front, rear, and second level provides multiple outdoor living spaces where panoramic bay views become the backdrop to everyday life. Inside, you’ll find a warm and inviting atmosphere highlighted by a cozy fireplace for crisp winter evenings. Recent improvements include updated bathrooms, a renovated kitchen, new kitchen appliances, fresh interior and exterior paint, new pier boards, and updated fencing, making this home move-in ready. A detached carport with an attached storage shed offers covered parking and plenty of room for all your beach gear, boating equipment, and tools. Just across the driveway sits an equally charming one-bedroom, one-bath guest cottage. Whether you use it for visiting family and friends, a private home office, or continue its success as a short-term vacation rental, it offers exceptional flexibility and income potential. Rarely does an opportunity like this come along. Own not one, but two highly sought-after vacation rental homes in the picturesque waterfront community of Scotland, Maryland. Whether you’re looking for a personal waterfront retreat, a family compound, or an income-producing investment, this exceptional Chesapeake Bay property delivers the best of coastal living.

14940 Chesapeake Bay Dr, Scotland

Listing courtesy of CENTURY 21 New Millennium. Contact:

24730 Half Pone Point Rd, Hollywood
$4,295,000
4 Beds ⋅ 7 Baths
A legacy waterfront estate at the tip of coveted Half Pone Point. Commanding one of the most prestigious waterfront settings in Southern Maryland, this extraordinary residence offers more than 14,000 square feet of meticulously crafted living space designed to capture breathtaking panoramic views of the Patuxent River from nearly every room. Architectural excellence and exceptional craftsmanship are evident throughout, blending timeless elegance with modern luxury. Designed for both grand-scale entertaining and comfortable everyday living, the estate features a private elevator, state-of-the-art theater room, wine room, game room, custom entertaining bar, and resort-style amenities including a spectacular infinity-edge pool and expansive outdoor living spaces. The property is further enhanced by advanced whole-home automation, integrated smart-home technology, comprehensive high-definition surveillance systems, a secure safe room, and numerous additional proprietary security features. For sport and recreation, the residence also includes a private indoor commercial-grade shooting range—a rare amenity seldom found in residential properties. Just minutes by boat from Solomons Island and the Chesapeake Bay, this remarkable property delivers an unparalleled waterfront lifestyle where privacy, sophistication, and natural beauty converge. Created for those who value discretion as much as luxury, certain features and specifications of the estate are intentionally withheld from public marketing materials. Qualified purchasers only. Private showings are available by appointment for financially qualified buyers. Proof of funds or lender pre-approval may be required prior to touring the property. Due to the nature of certain security, technology, and infrastructure systems, prospective purchasers may be asked to execute a confidentiality agreement before receiving access to selected property information and features.

24730 Half Pone Point Rd, Hollywood

Listing courtesy of HomeZu by Simple Choice. Contact:

208 Market St, Cumberland
$975,000
First time on market since 1980 Originally the Ice House for Queen City Brewery, converted to 6 bay truck repair facility in 1980 and successfully operated into 2024. 1.47 acres plus useful areas in public easements. Large brick - steel industrial building (1900) building with 7 large drive in doors, 12,952 measured main floor PLUS 3,386 Concrete roof decks with well maintained roofing. Built to handle massive floor loads. Just 1,500' from the center of town - big useful building with a very big parking lot. Property is adjacent to but outside of Historic District. Over 500' frontage on Wills Creek, WMSR Scenic RR, GAP Trail eastern terminus/ C&O canal Western Terminus @ Canal Place is 1/4 mile walk away. Great opportunity to continue with truck repair/inspections/parts use or redevelop into Night Club Health Club Recreational Uses, Restaurant, Loft Apartments, Antiques, Art Gallery, Retail....

208 Market St, Cumberland

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

12301 Jamaica Ave Unit 351N, Ocean City
$499,900
2 Beds ⋅ 2 Baths
Welcome to this beautifully updated top-floor 2-bedroom, 2-bath waterfront condo in Hidden Harbour III, complete with Boat Slip #98. Ideally located just a few blocks from the beach and within walking distance of Northside Park, this fully furnished property is move-in ready and waiting for you to start enjoying the coastal lifestyle. The complex has a pool to enjoy on those hot summer days. The updated kitchen features custom white cabinetry, granite countertops, stainless steel appliances, a breakfast bar, and a custom wine and coffee bar with additional serving space—perfect for entertaining. The dining area flows seamlessly into the spacious living room, where large sliding glass doors frame beautiful canal views and fill the space with natural light. Step outside to the recently replaced oversized composite waterfront deck, complete with an awning for shade and a convenient storage closet. It's the perfect setting for enjoying summer crab feasts, relaxing with your morning coffee, or watching the boats cruise by. Boat Slip #98 is located directly below the deck, providing easy access for boating enthusiasts. You'll also enjoy front-row views of the spectacular Northside Park fireworks throughout the summer. The spacious primary suite offers a king-sized bed, two closets, and an updated en-suite bath featuring a custom-tiled walk-in shower. The second bedroom comfortably accommodates family and guests with a queen-sized bed and easy access to the full hall bath with a tub/shower combination. A full-size washer and dryer are conveniently located in the unit, and the water heater was replaced in 2025 for added peace of mind. Whether you're searching for a primary residence ,or vacation getaway, this exceptional waterfront condo offers the perfect combination of location, comfort, and boating convenience. Conveniently located close to the beach, Northside Park, popular restaurants, shopping, and all that North Ocean City has to offer.

12301 Jamaica Ave Unit 351N, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact:

12355 Southhampton Dr, Bishopville
$2,795,000
5 Beds ⋅ 6 Baths
Welcome to 12355 Southampton Drive, the crown jewel of Lighthouse Sound, one of the Eastern Shore's most prestigious waterfront golf communities. This is a rare opportunity to own arguably the finest homesite in the neighborhood, where this extraordinary custom residence captures sweeping panoramic views of Assawoman Bay and the sparkling Ocean City skyline from nearly every rear-facing room. A dramatic two-story foyer with a graceful curved staircase sets the tone, drawing your eye straight through the soaring great room to the breathtaking water beyond. The two-story family room is anchored by a stunning natural stone fireplace with gas insert, creating an unforgettable gathering space framed by walls of glass. Designed for both everyday living and effortless entertaining, the chef's kitchen features gas cooking, granite countertops, a large center island, breakfast bar, sunny dining nook, walk-in pantry, and a fully equipped butler's pantry complete with wet bar and sink. Every space is thoughtfully connected to the expansive rear decks, ensuring the spectacular views are always part of the experience. The luxurious first-floor primary suite is a true private retreat, offering direct deck access, uninterrupted bay views, two professionally organized walk-in closets, and a spa-inspired bath with dual vanities, soaking tub, and oversized walk-in shower. A private study, spacious dining room, and main-level laundry complete the first floor. Upstairs, an impressive open landing overlooks the great room below and leads to four generously sized guest suites, each with private vanity and dressing areas and convenient en-suite bath access, providing exceptional comfort for family and guests alike. The outdoor living is every bit as remarkable as the interior. Nearly 1,700 square feet of wraparound Trex decking spans the rear of the home across two levels, creating an unparalleled setting for morning coffee, sunset cocktails, entertaining under the stars, or relaxing around the fire pit while watching boats drift across the bay and the Ocean City skyline come alive each evening. During the summer, enjoy a front-row seat to the free fireworks display every Sunday evening, launched from Northside Park just across the bay, a spectacular tradition that can be enjoyed from the comfort of your own deck. Additional highlights include Brazilian cherry hardwood flooring throughout, an oversized three-bay garage with abundant storage for vehicles and water toys, recessed lighting, ceiling fans, and quality craftsmanship throughout. Residents of Lighthouse Sound enjoy championship golf, an elegant clubhouse, dining, and one of the most spectacular waterfront settings on Maryland's Eastern Shore. Luxury. Views. Lifestyle. Rare opportunity. This isn't simply a home, it's a front-row seat to one of the most breathtaking waterfront panoramas on the East Coast. Once you experience the views from 12355 Southampton Drive, everywhere else feels ordinary.

12355 Southhampton Dr, Bishopville

Listing courtesy of Northrop Realty. Contact:

27174 Champ Wharf Rd Champ Wharf Unit 27174, Princess Anne
$299,500
2 Beds ⋅ 2 Baths
MOTIVATED SELLER HOME WARRANTY AVAILABLE WITH ACCEPTED OFFER This home has a recent appraisal 290,000, with copy posted in the document section of the MLS The perfect getaway! This beautiful 2-bedroom 2 bath waterfront home is located on the quiet St Peter's Creek. This well-maintained home has a new well and water filtration system along with new bathrooms and flooring. You will be surrounded by open countryside and the soothing sounds of nature for a perfect backdrop for both relaxation and adventure. This peaceful environment invites you to slow down and appreciate the simple joys of life. Entertain on the large deck or just relax with your favorite book. Launch your kayak, canoe or paddleboard from the convenience of your backyard or access the St. Peter's Marina, just a few hundred yards away, with a larger vessel. This home must see to be appreciated. HOME WARRANTY AVAILABLE WITH ACCEPTED OFFER

27174 Champ Wharf Rd Champ Wharf Unit 27174, Princess Anne

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

26279 Deep Water Harbor Rd, Easton
$2,995,000
4 Beds ⋅ 4 Baths
Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

26279 Deep Water Harbor Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

20 Shore Walk Rd, Riva
$1,775,000
4 Beds ⋅ 4 Baths
Located on the South River in Riva, within the Greater Annapolis area, this custom-built waterfront home is tucked away on a private lane shared by just three homes, offering the perfect blend of privacy, tranquility, and unforgettable panoramic open-water views. Completed in 2022, it combines timeless design, luxury finishes, and the peace of mind that comes with newer construction, allowing you to spend more time enjoying the waterfront and less time maintaining your home. Designed to make the most of its exceptional setting, every detail reflects thoughtful planning, quality craftsmanship, and timeless style. The main living areas were designed to capture the river views, with expansive windows that fill the home with natural light and create an easy connection to the outdoors. At the heart of the home, the gourmet kitchen features 42-inch cabinetry, stainless steel appliances, a generous center island, abundant pantry storage, and opens effortlessly to the dining and living areas, where the South River becomes the backdrop to everyday living. A dedicated office on the main level provides the perfect work-from-home space and can easily serve as a guest bedroom, adding flexibility to fit your lifestyle. Step outside to the waterside deck and take in the panoramic South River views, where boats, wildlife, and spectacular sunsets create a backdrop that changes every day. The primary suite is a private retreat featuring its own waterfront balcony, a spacious sitting area, oversized walk-in closet, and a spa-inspired bath complete with a luxurious steam shower. The walk-out lower level expands the home's living space with radiant heated floors, a full wet bar, and direct access to the waterfront, providing exceptional flexibility for entertaining, recreation, overnight guests, or multigenerational living. The waterfront lifestyle extends well beyond the home with exceptional community amenities, including a waterfront clubhouse, boat ramp, kayak launch, fishing pier, and community piers, making it easy to enjoy everything the South River has to offer. Here, you'll enjoy the rare combination of waterfront privacy and everyday convenience, just minutes from historic Annapolis, Edgewater, local coffee shops, waterfront dining at Mike's Crab House, and convenient access to Routes 50 and 97. Whether you're searching for a full-time waterfront residence or the perfect weekend retreat, this home offers the very best of South River living. Come experience it for yourself.

20 Shore Walk Rd, Riva

Listing courtesy of Engel & Volkers Annapolis. Contact:

104 Port Ct, Grasonville
$1,200,000
4 Beds ⋅ 3 Baths
WATERFRONT LIVING ON WINCHESTER CREEK! Welcome to this incredible 4-bedroom, 2.5-bath Grasonville estate offering the ultimate Eastern Shore lifestyle. The home is fully refreshed with a freshly painted neutral interior, gleaming hardwoods, and plush new carpet. A grand 2-story foyer with a Palladian window welcomes you inside to a main level featuring soaring 11' ceilings, a great room with a gas fireplace, and a striking bank of windows framing gorgeous water views. The main-floor primary suite boasts a walk-in closet and a zero-threshold shower. Two additional generously sized bedrooms, a full hall bath, and a guest powder room complete the main-level living spaces. Entertaining is a breeze in the bright breakfast room and fabulous kitchen, which features newer appliances, a separate pantry, and a center island. The separate dining room, with its soaring ceiling and wall of windows, is the absolute chef's kiss. Upstairs, a versatile bonus space with custom built-ins serves as a perfect home office or media room. Your outdoor resort awaits! A Trex deck with built-in benches and a retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the convenience of their own deeded boat slip (#10), mooring pile, and private boat lift on Winchester Creek just a short walk away, offering protected deep-water access directly to the Chester River and Kent Narrows. Experience the legendary Eastern Shore dock-and-dine lifestyle by boat or car, with regional favorites like The Narrows, Bridges, and the brand-new Dock House just minutes away. Enjoy close proximity to trails at CBEC, shopping, top-tier healthcare at , and highly regarded . This estate beautifully pairs absolute waterfront tranquility with everyday convenience! Mechanics & Storage: Main-level laundry with sink, oversized 2-car garage with multiple storage rooms, HVAC (2018), buried 500-gallon propane tank, and a fully serviced water conditioning system with reverse osmosis.

104 Port Ct, Grasonville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

13 Widows Watch Ct, Ocean Pines
$1,295,000
4 Beds ⋅ 4 Baths
Original lot for Boise Cascade to promote Ocean Pines from their sales center when it was first being developed. The original house was torn down and this lovely home eminates the spirit of Ocean Pines! Located on a wide canal with gorgeous evening sunsets will captivate you. The beautiful, open, floorplan is a must see... great for entertaining and admired by family and friends. There is close access to the Assawoman Bay and the Swim and Racket Club. The primary suite is on the main level with it's own private bath.

13 Widows Watch Ct, Ocean Pines

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

1876 Potomac Rd, Pasadena
$869,000
3 Beds ⋅ 3 Baths
Impeccably maintained and thoughtfully redesigned and rebuilt, this waterfront home features striking curb appeal and an open floor plan on a picturesque 0.53-acre lot. Enter through a dramatic two-story foyer into the entry level which includes a formal dining area, two generously sized bedrooms and a full bath. A half flight of stairs leads to the lofted great room with an open plan that integrates the kitchen with center island (cooktop & wall oven), granite countertops, black French-door refrigerator, dining area and living room beneath soaring cathedral ceilings. The great room's living area features a stacked-stone fireplace with a gas (LP) insert—ideal for Maryland’s cooler months. Sliding doors from the great room open to a large composite deck with vinyl rails overlooking the scenic tributary where waterfowl thrive and owners have enjoyed years of crabbing. The primary suite, positioned for water views, includes a private full bath and cathedral ceilings. The fully finished lower level offers a second living space with an accent wall of stacked stone, stacked stone dry bar, a generous laundry/work room, and walkout access to the waterfront patio, hot tub, yard and private pier. The property features approximately 150' of water frontage on Wharf Creek of the Bodkin, a private pier with a 15,000 lb boat lift, PWC lift (set up for 1 with weight capacity for 2), and average water depth of 4'. Additional amenities include an attached two-car garage, with a private, conditioned room perfect for a home office, a separate workshop/she-shed with A/C unit, an additional storage shed, and a concrete driveway. Generac whole house generator powers most of the house, including the well pump and heat. Roof replaced in 2019. Located near the mouth of the Bodkin and just minutes from the Chesapeake Bay, this home provides convenient access to open water, making it an appealing choice for boating enthusiasts . In 30-50 minutes, boat to Annapolis, Rock Hall, Kent Island, the Magothy River and Baltimore. Enjoy sunrise and sunset anchoring in the basin where Main Creek and Back Creek converge near the mouth of Bodkin Creek. Walk or bike to scenic Downs Park via Green Gables pedestrian access just a few feet from your front door. Downs Park offers trails, picnic pavilions and summer concerts. Convenient to Baltimore, Annapolis and DC, this property is ideal for full-time living or a second home. Make an appointment today and experience the Bay Life!

1876 Potomac Rd, Pasadena

Listing courtesy of Keller Williams Flagship. Contact:

24050 Macs Ln, Worton
$895,000
3 Beds ⋅ 3 Baths
****NEW PATH TO WATER FOR YOUR GATOR OR UTV**** This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect "magnet house" to attract friends and family or an amazing investment opportunity.

24050 Macs Ln, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

6355 Bozman Neavitt, Neavitt
$849,900
3 Beds ⋅ 2 Baths
Offered for the first time in nearly 30 years, this charming waterfront bungalow on Duck Cove has been lovingly maintained and thoughtfully improved by its current owners. Filled with warmth and character, the home showcases beautiful original woodwork, hardwood floors, and a cozy wood-burning fireplace that creates an inviting atmosphere year-round. The main level features a spacious kitchen, convenient separate laundry room large dining area perfect for family dinners or entertaining. Plus a half bath, making everyday living easy and comfortable. A standout feature is the completely renovated 12' x 27' screened porch, where you can relax and enjoy peaceful views overlooking Duck Cove. Outside, waterfront living shines with an outside shower, a new pier, boat lift, ample space for kayaks, paddleboards, and other water toys, plus a storage shed for all your essentials. The generous half-acre lot offers the perfect balance of sun and shade, creating an ideal setting for gardening, entertaining, or simply enjoying nature. Upstairs, the light-filled second floor provides bright and comfortable living spaces, while the home's timeless charm and waterfront setting make it truly special. A rare opportunity to own a cherished waterfront retreat in sought after Neavitt. Bonus - much of the furnishings can convey. Agents - please read remarks

6355 Bozman Neavitt, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact:

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