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$849,999
4 Beds 4 Baths
Luxury Waterfront Living with Private Deeded Boat Slip in the exclusive gated community of Waters Edge at Seneca Creek! This former model home is just a few years old and loaded with upgrades, premium finishes, and breathtaking water views from nearly every level. This elegant 4-bedroom, 4-bath home offers over four levels of thoughtfully designed living space. The entry level welcomes you with custom built-ins, ceramic flooring, a spacious two-car garage, abundant storage, and a workshop area with walkout access to the yard. The main living level features an open-concept design with hardwood floors, abundant natural light, and spectacular water views. The gourmet kitchen is appointed with granite countertops, stainless steel Energy Star appliances, a gas range, oversized center island, breakfast area, and 42-inch white shaker cabinetry. Step outside to the expansive 26' x 14' composite deck overlooking Seneca Creek—perfect for entertaining or simply enjoying the stunning water views and natural surroundings. Upstairs, the luxurious primary suite includes a private sitting area with water views and a spa-inspired bath. Two additional generously sized bedrooms, a full bath, and conveniently located laundry complete this level. The top-floor loft provides exceptional flexibility as a bedroom, family room, home office, fitness space, or guest retreat. Complete with a wet bar, half bath, and access to a stunning 16' x 12' rooftop deck, this level offers some of the home's most spectacular waterfront views. Boating enthusiasts will appreciate deeded ownership of Slip #2 at the maintenance free community pier. Improvements include four additional pilings creating 2 slips- one with a 15,000-pound Magnum boat lift, and electrical service for both wet and dry dock capabilities, providing direct access to Seneca Creek and the Chesapeake Bay. Never mow another lawn or pull another weed as your HOA takes care of landscaping and lawn maintenance as well as upkeep of the community's private dock and beach area. Rarely does a home combine luxury finishes, panoramic water views, private boating access, and low-maintenance living so seamlessly. Move-in ready and truly one of the area’s premier waterfront offerings.

519 Schmidt Rd, Middle River

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$650,000
4 Beds 3 Baths
WATERFRONT LIVING ON BEAR CREEK! Welcome to this one-of-a-kind waterfront retreat featuring a private dock, direct water access, an in-ground pool and the ability to keep your boat right in your own backyard. Whether you're enjoying sunrise coffee overlooking the water or spending the day cruising the Chesapeake Bay, this property offers the waterfront lifestyle you've been dreaming of. SMART is the new LUXURY! Control your home from anywhere using your voice or phone - lock doors, adjust temperatures, control lighting, and see who's at the door with the touch of a button. Designed for entertaining, the outdoor oasis features an in-ground pool, hot tub, expansive outdoor living spaces, and stunning waterfront views. Inside, the gourmet kitchen is equipped with stainless steel appliances, quartz countertops, and plenty of space for hosting family and friends. The property is offered fully furnished, including furniture, decor, personal property, and game room amenities, making it completely turnkey. Just bring your suitcase and start enjoying everything this incredible home has to offer. The converted garage has been transformed into the ultimate game room featuring a pool table, foosball, air hockey, basketball arcade game, Xbox gaming system, pac-man, bar area and more. There is also an additional apartment-like bedroom, bathroom, kitchen and lounging area with its own entrance which provides the perfect setup for guests, extended family, or additional income potential. Unwind in the enclosed two-person Jacuzzi after a day on the water and enjoy resort-style living year-round. ATTENTION INVESTORS: This property has operated as a successful short/mid-term rental, averaging $15,000 per month in revenue. Whether you're searching for a primary residence, waterfront getaway, or income-producing investment, this rare Bear Creek property truly offers it all.

7810 Deboy, Dundalk

Listing courtesy of Lazar Real Estate. Contact: (443) 562-8498

$1,995,000
4 Beds 3 Baths
Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

9020 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$1,750,000
7 Beds 5 Baths
Opportunities like this don’t just happen—they are discovered. 1100 Cataway Place is a truly special diamond in the rough, a sprawling 13-acre waterfront sanctuary defined by multi-million dollar views that are nothing short of legendary. Situated directly across the Potomac from George Washington’s Mount Vernon, this estate offers a vantage point where history and nature collide in a spectacular, panoramic display. The water is the focal point of the entire experience here. Whether you are wandering the expansive grounds, relaxing in the main residence, or standing on the guest house deck, the shimmering Potomac and the iconic silhouette of Mount Vernon are your constant companions. The property features two beautifully renovated residences that lean into this incredible backdrop. The primary home exudes sophisticated warmth, with four spacious bedrooms and three full baths. Throughout the sun-drenched interiors, rich hardwoods lead the eye toward nearly every window, each perfectly framing a different, breathtaking perspective of the river. Just a few steps away, the guest house is a gem in its own right. Fully updated with three bedrooms and two full baths, its standout feature is a private Trex deck designed specifically for soaking in those wide-angle water views as the sun dips below the horizon. The land itself is a private world of lush woods, a tranquil pond, and expansive open fields that all seem to point back toward the river's edge. It’s a place that feels worlds away from the hustle, yet the energy of Washington, D.C. is reachable in 40 minutes. Whether you envision a private legacy estate, a high-end retreat, or a creative venue, this is a one-of-a-kind chance to own a piece of history with a view that is truly priceless.

1100 Cataway Pl, Bryans Road

Listing courtesy of Compass. Contact: (240) 219-2422

$1,250,000
5 Beds 5 Baths
DESIRABLE LOCATION! Huntingtown's premier Waterfront community, Holland Cliff Shores, is nestled along the banks of the Patuxent River! This show-stopping Cape Cod is more than a home — it’s a lifestyle! With 5 bedrooms, 4.5 bathrooms and 5056 square feet of thoughtfully designed living space (not including the 2 bed 1 bath apartment above the garage leased for $20,700/year)! Located on 1.4 acres, this waterfront retreat pairs timeless craftsmanship with breathtaking natural beauty visible from all bedrooms! We have verified a PIER CAN BE INSTALLED! From the moment you arrive, the stately brick exterior and welcoming front porch set the tone for what’s inside — warmth, comfort, and classic elegance. Step through the double doors into a grand foyer framed by oak and pine finishes, opening to a wide, sun-drenched living space where the river immediately steals the show. Walls of glass invite you to take in panoramic views from nearly every room, while rich hardwood floors, wood framed beams, and a handsome brick fireplace anchor the open-concept main level in charm and sophistication. The kitchen is a dream for both everyday living and entertaining, boasting white cabinetry, granite countertops, stainless steel appliances, and an expansive peninsula that flows into the dining area. As meals are shared and laughter fills the air, the glow of the fireplace and glimmer of the water beyond create a feeling that’s both intimate and grand. Step through the sliding doors to a sprawling covered deck — the perfect place for morning coffee, nature watching, or toast to another stunning Southern Maryland sunset. Upstairs, the very large primary suite offers a front-row seat to the river with access to an upper level full length covered porch and a cozy wood-burning fireplace. The ensuite bath is an indulgent escape featuring a custom tiled two-person shower, an oversized free standing soaking tub, a 9' custom vanity w/ a Calacutta Quartz vanity top, water closet, and access to the walk-in closet w/ custom built-ins. Two additional bedrooms w/ river views and porch access are serviced by a well appointed hall bathroom. Just off the primary bathroom, a large laundry area serves as a pass through to the bonus room/bedroom located above the attached garage. The massive suite offers versatility at its finest. Accessible from inside the home or by a private exterior entrance, this oversized retreat could serve as a guest suite, home office, studio, or teen hideaway. Downstairs, the fully finished walkout basement expands your living and entertaining options. Here you’ll find a large recreation room with a full bar — ideal for game nights or weekend gatherings — plus a wood-burning fireplace that adds warmth and character. Behind the bar, discover a hidden vault room ready for your wine collection, workshop, or secure storage. A full bath and 5th bedroom provide even more flexibility for guests, hobbies, or an office. Step outside and follow the stairs down to your private kayak dock on the Patuxent River. Whether you’re kayaking at sunrise, fishing in the afternoon, or relaxing with a glass of wine at dusk, this is a place where every day feels like a getaway. And just when you think this home couldn’t offer more, it does — with a beautifully renovated 2 bedroom 1 bathroom apartment above the detached garage. This space features a modern kitchen with granite counters, stainless appliances, in-unit washer and dryer, and a private deck. It’s the ideal setup for multi-generational living, an au pair, visiting guests, or rental income potential. From top to bottom, this property exudes craftsmanship, versatility, and serenity. It’s the kind of home where memories are made — gatherings by the fire, sunlit mornings on the deck, and quiet evenings as the river reflects the sky. This isn’t just a house on the water. It’s the life on the water you’ve been dreaming of. Schedule your private showing today!

3017 Abington Manor Dr, Huntingtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$900,000
3 Beds 2 Baths
Whether you're searching for a luxurious vacation retreat, year-round residence, or exceptional investment opportunity, this true “must-see-to-appreciate” property offers the very best of Ocean City living and a rare opportunity to own your own piece of paradise. Experience luxury coastal living at its finest in this exceptional south-corner residence at 11400 Coastal Hwy #8J. Showcasing breathtaking oceanfront and bay views, this stunning end-unit retreat is filled with natural light and offers a rare 3-bedroom, 2-bath layout within the High Point North complex. A true standout feature, the unit enjoys the privilege of witnessing both full Atlantic Ocean sunrises in the morning and serene Assawoman Bay sunsets in the evening—delivering unmatched daily scenery and elevated lifestyle appeal. Completely rebuilt and designer-renovated with no detail overlooked, the residence was reconstructed in 2016 with 6-inch exterior walls and premium craftsmanship throughout. Interior highlights include custom cabinetry, quartz countertops, stainless steel appliances, recessed lighting, pocket doors, updated windows and railings, a tiled lanai entry, and a beautifully finished oceanfront balcony with storm shutters. Modern comforts include updated HVAC units and a fully permitted reconfigured floor plan designed for both elegance and functionality. While the current owners have not rented the condo during their 8 year tenure, the unit is positioned as a high-performing rental opportunity, given that this residence offers strong short-term vacation appeal supported by its premier location, rare layout, and turn-key condition—an ideal asset for investors seeking both lifestyle enjoyment and income potential. Located in a meticulously maintained, self-managed oceanfront building, residents enjoy a large beachfront pool and sundeck, low-density beach access, seasonal security, updated lobby and elevators, abundant open parking, and covered parking space #HA. The condo fee includes basic cable and reserve contributions, further enhancing the value of this exceptional coastal investment.

11400 Coastal Hwy Unit #8J, Ocean City

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$515,000
3 Beds 3 Baths
Opportunity awaits as we welcome you to this beautifully updated waterfront home located on Leonard Mill Pond in the quiet residential neighborhood of Holly Lake Estates. Classic charm meets modern comfort in this three bedroom, three bath residence which offers stunning water views through expansive waterfront windows that fill the home with natural light and showcase the tranquil surroundings. The heart of the home features custom cabinetry and thoughtfully updated living spaces designed for both everyday living and entertaining. Relax year-round on the inviting screened porch complete with a wood burning fireplace, the perfect spot to enjoy peaceful mornings, cozy evenings and picturesque pond views. Sellers are motivated so make an appointment to see this treasure and bring an offer. Additional highlights include a full basement providing ample storage and flexible space, an attached garage with an additional full bathroom. The numerous unique architectural details set this property apart. Whether you are looking for a primary residence or a waterfront retreat, this property offers a rare opportunity to enjoy the beauty and serenity of Lenoard Mill Pond.

8539 E Marlboro Dr, Delmar

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$525,000
Land Only Listing! Build your dream home on this exceptional waterfront lot with a private pier. This cleared, corner lot on a cul-de-sac offers breathtaking panoramic views of both sunrise and sunsets. Enjoy the added benefit of a bulkhead protected by riprap rock, ensuring durability. The property has access to public water and sewer managed by Charles County. Don’t miss this incredible opportunity! As a resident of Swan Point, you'll enjoy a variety of community amenities, including an Olympic-size pool overlooking the water, walking and biking trails, tennis and racquetball courts, a marina, and a sandy picnic area by the Potomac River. The beautiful 18-hole golf course features a putting green and driving range. The Country Club's Restaurant and Bar offers a wonderful dining experience for those evenings when you don’t feel like cooking, along with engaging events such as wine tastings, painting parties, murder mystery dinners, Sunday brunches, and a Summer Concert Series on the veranda. Note*** Just a 25 min drive to Dahlgren Naval Base and an hours drive to Joint Base Andrews and Patuxent River Naval Base. Other exciting conveniences to note, we are a quick 10 minute drive to Cobb Island where there are 4 waterfront restaurants, night life, the Cobb Island Market (offering groceries, fresh produce and a butcher on site) and a Dollar General. Also, Walmart and Target both deliver to the neighborhood! This property isn’t just a home; it’s a lifestyle. Don’t miss your chance to own this exceptional waterfront property! CALL THE LISTING AGENT FOR AN APPOINTMENT TODAY!

11210 Keokee Ct, Issue

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$1,499,900
5 Beds 4 Baths
**COMPLETELY REIMAGINED WATERFRONT RETREAT ON BACK CREEK IN SOLOMONS!** Set on 3.29 private acres within walking distance to Solomons, Maryland, this completely remodeled 4500sqft waterfront retreat w/ 493 ft of Back Creek frontage blends luxury, privacy, and lifestyle. This exceptional property offers 5 Bedrooms, 4 Full Bathrooms, two primary suites, incredible outdoor living spaces, and a premier boating setup rarely found in Southern Maryland. From the moment you arrive, the setting immediately feels different. Mature trees, expansive lawn space, and panoramic water views create a peaceful waterfront backdrop while the beautifully updated home blends modern coastal finishes with comfortable everyday living. Inside, open living spaces are filled with natural light and designed to maximize the water views. Warm hardwood flooring, custom trim work, recessed lighting, oversized windows, and designer finishes create a home that feels both refined and inviting. The kitchen is the centerpiece of the home with custom cabinetry, quartz countertops, stainless appliances, floating wood shelving, designer fixtures, and a large statement island built for gathering and entertaining. The layout flows effortlessly into multiple living spaces while keeping the waterfront constantly in view. The formal living room offers warmth and character with a beautiful wood-burning fireplace as the focal point, perfect for cozy evenings or entertaining guests. Just beyond, the family room was designed around the views, featuring expansive picture windows overlooking Back Creek and creating a bright, open waterfront gathering space. One of the home's most unique features is the layout itself. The first primary suite is privately positioned toward the rear of the home with a large laundry room separating it from the main living spaces. A stunning breezeway with oversized sliding glass doors on both sides connects the suite to the main part of the home, filling the transition space with natural light and views of the surrounding property. The primary bath feels straight out of a luxury resort with extensive custom tile work, dual vanities, soaking tub, and oversized walk-in shower. The second primary suite offers its own beautifully remodeled ensuite featuring a striking black-and-white design, modern finishes, dual vanity areas including a dedicated makeup vanity, and an oversized custom shower—ideal for guests, multigenerational living, or extended stays. Two additional decent-sized bedrooms and a large hall bathroom complete the main floor. The hall bath is equipped with a large vanity w/ double drawer stack cabinets, quartz countertops, and a beautifully tiled shower. The finished basement offers additional living space, including a bonus room that could serve as a 5th bedroom, guest suite, home office, hobby room, or fitness space, plus a large recreation/media area. Outside, the property transforms into a true waterfront escape. A massive waterside deck overlooks Back Creek and creates the perfect space for entertaining, dining, or simply relaxing while taking in the peaceful setting. A custom paver stone gas firepit with granite surround creates another incredible outdoor gathering space tucked perfectly into the landscape. Near the shoreline, a large 14x16 storage shed with surrounding decking provides ideal space for boating equipment, fishing gear, paddleboards, and waterfront storage while offering another place to enjoy the views. At the water's edge, the private pier is designed for serious boating enthusiasts with an impressive 60x20 slip on one side and a 40x16 slip on the other, offering exceptional dockage rarely available on protected waters like Back Creek. Completing the property is a detached 4-car garage, extensive hardscaping, mature landscaping, and rare acreage with protected waterfront living—all just moments from Solomons' restaurants, marinas, and waterfront lifestyle.

160 Bamboushay Ln, Solomons

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$389,000
3 Beds 1 Baths
Opportunities like this don't come up often. 7607 Chesapeake Ave presents two separate waterfront parcels in Sparrows Point with utilities already at the street and a clear path to development. The existing structure carries no value, the opportunity is entirely in the land. The parcels are separated by a road and are best treated as two independent building sites. That distinction opens the door to a range of strategies: build on one and hold the other, develop both independently, or sell one to offset your cost basis on the second. Buyers should conduct their own due diligence on parcel configuration and permitted uses. Utilities already at the street is a meaningful advantage on a waterfront lot. Extending service from scratch adds real cost and timeline to any project before a single foundation is poured. That groundwork is already done here. The surrounding street tells the story, custom homes built in 2002 and 2023 sit on either side, evidence that buyers who've recognized this waterfront location have acted on it. Whether you're planning a primary residence on the water or evaluating this as a development play, 7607 Chesapeake Ave is worth a close look. Call or text today to learn more.

7607 Chesapeake, Edgemere

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$1,075,000
4 Beds 3 Baths
Exceptional canal-front home with a pier and direct access to the bay. Thoughtfully updated throughout, this spacious 4-bedroom, 2.5-bath home offers the potential for a 5th bedroom and features new windows, flooring, renovated bathrooms, and an updated kitchen. Modern glass stair railings add a stylish contemporary touch, while the primary suite boasts a generous walk-in closet. Enjoy stunning water views from the spacious living areas, screened porch, and multiple decks. Outside, the beautifully landscaped and fenced yard provides the perfect setting for entertaining or relaxing by the water. Additional features include a fireplace, attached 2-car garage, and pier for boating, fishing, and crabbing right from your backyard. Ideally located just around the corner from one of Ocean Pines waterfront beach clubs, residents can enjoy convenient access to a pool, sandy beach area, and waterfront recreation. Enjoy all the amenities Ocean Pines has to offer, including pools, golf, marina, yacht club, parks, and beach club access. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this exceptional waterfront property offers the best of coastal living.

9 Harborview Dr, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382

$6,995,000
4 Beds 6 Baths
Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in 2017 by renowned architect Cathy Purple Cherry, this residence was rebuilt and renovated to an exceptional standard, blending timeless coastal architecture with modern luxury and uncompromising construction quality. Spray-foam insulated walls and roof, steel reinforcement, double plywood construction, four-zone HVAC with humidifiers, gas backup heat, tankless propane water heaters, water treatment systems, generator backup, Sonos audio, and Lutron lighting create a home that is as efficient and functional as it is beautiful. Designed for both grand-scale entertaining and comfortable everyday living, the interior offers over-the-top craftsmanship and thoughtful details throughout. Maple hardwood flooring flows through elegant yet inviting spaces including a dramatic waterfront living room with a custom wet bar, an informal gathering room with built-in bookshelves, a private office with custom cabinetry, wet bar, balcony, and commanding views stretching down the Chesapeake Bay, and a state-of-the-art theater room complete with its own wet bar, refrigerator, and ice maker. The chef’s kitchen is a masterpiece featuring double Wolf ovens, Wolf cooktop, Sub-Zero refrigerator, three dishwashers, wine cooler, ice maker, built-in microwave, instant hot water, walk-in pantry with custom built-ins, and a sun-filled breakfast nook overlooking the water. The luxurious primary suite serves as a private waterfront retreat, highlighted by a stunning spa bath finished with Italian water-cut marble. Three additional bedrooms feature ensuite baths, while a full bath on the main level conveniently serves the pool and outdoor entertaining areas. Outdoor living rivals the finest resorts. Expansive Ipe decking surrounds a heated PebbleTec pool and spa, complemented by an outdoor kitchen, fire pit, integrated sound system, and extensive landscape lighting. The private pier is equipped with water, electric, approximately 4 feet of MLW, a 12,000-pound boat lift, an 8,500-pound boat lift, and a 1,500-pound personal watercraft lift, providing immediate access to the Chesapeake Bay and beyond. Offering 4 bedrooms, 5 full baths, 1 half bath, a dedicated office, and a deep four-car garage, this is a rare opportunity to own one of Annapolis’ premier waterfront properties in a setting where extraordinary architecture, unmatched craftsmanship, and world-class outdoor living come together on the shores of the Chesapeake.

3728 Ramsgate Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$389,000
1 Beds 2 Baths
Experience the best of coastal living in the highly sought-after Old Port Cove West community. Situated along a canal with quick access to the open bay, this beautifully maintained bi-level townhouse offers approximately 1,002 square feet, 1 bedroom, 1.5 baths, and an expansive upper-level loft that comfortably functions as a second bedroom, giving the home the feel and functionality of a 2-bedroom property. The main level features an open living and dining area, a half bath, and a kitchen with all brand-new, never-used appliances that can be registered by the new owner. Sliding glass doors lead to a spacious canal-front deck overlooking the water. Boating enthusiasts will appreciate the private boat lift and direct canal access just steps from the back door, offering quick access to the open bay for boating, fishing, waterfront dining, and exploring the coastal waterways. The canal is also ideal for kayaks, paddleboards, and other small watercraft. Residents of Old Port Cove West enjoy access to a community pool, beautifully maintained grounds, and numerous recent community improvements, including repaved parking areas, updated roofs, new siding, recently completed bulkhead, and upgraded decks. Whether you're searching for a full-time residence, weekend retreat, investment property for rental income, or seasonal getaway, this canal-front property offers an exceptional combination of comfort, convenience, and coastal charm.

2819 Plover Dr Unit #43, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$7,995,000
8 Beds 10 Baths
Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment. The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle. Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining. The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests. Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility. This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

7328 Kent Point Rd, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$650,000
Welcome to 182 Waldo Road in Pasadena offered at $650,000. An exceptional waterfront redevelopment opportunity on nearly three-quarters of an acre in Pasadena. The existing home is considered a tear-down, creating a rare chance to build a custom waterfront residence tailored to your vision. What sets this property apart is that many of the most expensive waterfront improvements are already in place. The property features a substantial private pier that was constructed in 2022, including multiple slips, providing immediate access to the water and saving a future owner the time, expense, and permitting process associated with new marine construction. In addition, the property includes Anne Arundel County-approved septic plans for a new residence of approximately 2,500 square feet, approved in April 2026. Property Highlights: ✅ .72-acre waterfront homesite ✅ Existing pier built in 2022 featuring: 50' x 6' pier 10' x 20' L-head Multiple finger piers Additional mooring pilings (Originally constructed at a cost of approximately $62,900.) ✅ County-approved septic design for a new 2,500± sq. ft. home ✅ Existing approvals help streamline the path to construction ✅ Rare opportunity to create a custom waterfront retreat in Pasadena Whether you're a builder, investor, or buyer seeking the perfect waterfront homesite, 182 Waldo Road offers the chance to start with valuable infrastructure already in place and focus on designing the home you've always wanted.

182 Waldo Rd, Pasadena

Listing courtesy of Next Step Realty, LLC.. Contact: 4439012200

$489,900
2 Beds 3 Baths
his waterfront townhome offers two levels of comfortable living. Well cared for with recent updates include Freshly Painted with new vinyl floor on main floor, bulk heading, roof siding and porch. Open kitchen and living room, large private new deck with steps down to pier and boardwalk area. Private boat slip with a lift and quiet community. Large bedrooms with plenty of room for guest, and extended family. Walk to the boardwalk, beach, shops, amusements & restaurants. This townhome could rent very well, Small well run association, 2 assigned parking spaces, easy bay access by boat, hazard insurance, and internet-Wi-Fi covered in low condo fee. All Furniture and BOAT included in the sale.

2807 Plover Dr Unit #4, Ocean City

Listing courtesy of Fairfax Realty of Tysons. Contact:

$1,400,000
4 Beds 5 Baths
End each day with sweeping sunsets over Madison Bay from this exceptional waterfront compound offering 268 feet of protected, rip-rapped shoreline and 1.12 acres of privacy, ideally positioned with a coveted east-west orientation. A private pier equipped with a boat lift and personal watercraft lift enhances the property’s appeal, delivering immediate access to the water and an effortless boating lifestyle. Designed by renowned architect Burhsar Pathare, the impeccably crafted residence spans over 5,000 square feet across three finished levels, featuring 4 bedrooms and 4.5 baths, all thoughtfully positioned to capture unobstructed water views. Beautiful flooring flows throughout, complementing clean architectural lines and high-end finishes. The entry level welcomes you with a large living space highlighted by high ceilings and an abundance of windows that frame stunning water views. A beautiful, full-service bar—complete with sink, dishwasher, and high-end finishes—creates the perfect setting for entertaining. This level also features a spacious laundry and utility area along with a convenient half bath, and provides direct access to the backyard and waterfront setting for seamless indoor-outdoor living. Take the stairs or the elevator to access the upper levels of the home. The main level is truly striking, showcasing soaring 40-foot ceilings and a dramatic wall of glass capturing panoramic bay views. The open-concept design seamlessly integrates the kitchen, dining, and living areas, anchored by a stone fireplace. The gourmet kitchen features a spacious eat-in area and opens to a full-length wraparound deck overlooking the water—ideal for gatherings of any size. The main-level primary suite offers private deck access and a spa-like bath, with an additional full bath also located on this level. Upstairs, a loft overlooks the main living space, along with three generously sized bedrooms, including two ensuite bedrooms with private baths—each bedroom also features its own private deck overlooking the water, offering a peaceful retreat with breathtaking views. The third secondary bedroom features the added convenience of direct elevator access within the room itself. Outdoor living is equally impressive with multiple decking areas and a beautifully designed paver patio featuring a fire pit and sitting walls—all oriented to take full advantage of the waterfront setting. The property is fully fenced, enhancing both privacy and functionality. A gated entrance with electronic access further enhances privacy and security, while an oversized two-car attached garage provides ample convenience and storage. The property is serviced by public sewer and a private well. The residence is offered as a truly turnkey opportunity, conveying with the majority of its high-quality furnishings for an effortless, move-in-ready experience (select artwork and personal items excluded). The adjoining property at 1250 Old Madison Road is also available for purchase (MDDO2012114), featuring a charming 2-bedroom, 2-bath cottage with additional living space and expansive water views—ideal as a guest house or income-producing rental. An exceptional opportunity to fully embrace the waterfront lifestyle—where every day feels like a retreat and lasting memories are made. Mortgage savings may be available for buyers of this listing.

1252 Old Madison Rd, Madison

Listing courtesy of Redfin Corp. Contact: 3016586186

$699,000
4 Beds 3 Baths
Welcome to 35 Neptune Drive, a stunning 4-bedroom, 3-bathroom home on Rumsey Island with an expansive waterfront. Surrounded by water views and outdoor living spaces, this property offers an opportunity to enjoy the beauty, tranquility, and lifestyle that life on the water provides. Outdoor living is a highlight of this home. Step outside onto the patio, which opens to a spacious backyard and leads to a large waterfront deck overlooking the water. Continue down to your private dock, offering direct access for boating, fishing, kayaking, or simply relaxing while taking in the views. Inside, spacious living areas and tons of natural light create a welcoming atmosphere throughout the home. The primary suite includes a private sunroom overlooking the water, while a second sunroom on the main level provides additional space to relax and enjoy the scenery. Located on historic Rumsey Island, where the Big and Little Gunpowder Falls meet, residents enjoy a community known for its scenic surroundings, rich history, and coastal atmosphere. Whether you're spending the day on the water, entertaining guests on the deck, or enjoying a quiet evening watching the sunset from your backyard, 35 Neptune Drive offers a rare opportunity to enjoy waterfront living on Rumsey Island.

35 Neptune Dr, Joppa

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3840

$550,000
3 Beds 2 Baths
Priced below tax assessed value, this rare waterfront retreat on beautiful White’s Neck Creek offers a renovated guest house, private dock, and true Southern Maryland charm. Set on over half an acre in the established River Springs waterfront community, 37526 River Springs Road offers the kind of lifestyle buyers wait years to find: peaceful water views, navigable creek access, private outdoor space, and a move-in ready setting that feels tucked away while still being accessible. The main residence is warm, inviting, and tastefully updated with comfortable living spaces, natural light, and serene views of the water and surrounding trees. What truly sets this property apart is the renovated waterfront guest house, creating a rare two-residence setup ideal for visiting family, extended stays, a private office, studio, or flexible guest accommodations. Outdoor living is the centerpiece. Enjoy mornings by the creek, evenings on the deck, and weekends crabbing, fishing, kayaking, or relaxing by the water. The property also features a private dock, crab/oyster shack, and a large storage/workshop building near the front of the property, offering excellent space for tools, equipment, hobbies, waterfront gear, or future possibilities. Located near St. Catherine Island and Bullock Island, this property combines renovated living space, guest accommodations, usable land, private dockage, and memorable water views in one truly special creekside setting. Schedule your showing and experience the waterfront lifestyle for yourself.

37526 River Springs Rd, Avenue

Listing courtesy of Innovation Properties, LLC. Contact: 7037824422

$799,755
4 Beds 2 Baths
Stunning Waterfront Home with Deep Water Access & Exceptional Outdoor Living Experience serene, panoramic water views from this beautifully updated waterfront retreat offering 5 ft MLW, a private pier that could be extended, (see plan in the pictures of a proposed 40 ft+ pier), and space for multiple boats. Blending comfort, style, and functionality, this home is perfect for year‑round living or a luxurious weekend escape. Main Level Highlights Open‑concept living — Spacious family room with a gas fireplace and sliders leading to a 24' x 12' screened‑in porch (2022), built with maintenance‑free materials, two skylights, and sweeping water views. Renovated kitchen — Quartz countertops, stylish backsplash, upgraded stainless steel appliances, and durable LVP flooring. Semi‑formal dining room — Perfect for gatherings and entertaining. Main‑level bedroom — Large full bath with a double vanity. Waterfront office — Generous closet; ideal for work, hobbies, or flexible use. Second Level Features Expansive primary suite — Includes a private 16' x 11' screened‑in covered porch overlooking the water. Luxury primary bath — Seamless‑door 4 ft shower, elegant soaking tub, double sinks, and walk‑in closet. Two additional bedrooms — Well‑sized and full of natural light. Large laundry room — 16' x 8' with potential to convert into a third full bath. ⚙️ Exterior & Mechanical Features Oversized 2‑car garage Concrete driveway accommodating 5+ vehicles Two‑zone HVAC, with one system only 3 years old Natural gas already connected Private pier with new decking Deep water suitable for multiple boats. Prime Location and $10,000 in closing help from the seller This home is within walking distance to restaurants, a shopping center, and numerous local conveniences — offering the perfect blend of waterfront tranquility and everyday accessibility.

40 Johnson Rd, Pasadena

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$329,900
2 Beds 2 Baths
Welcome to 113 NE Isle Dr located in the beautiful, water oriented community of North East Isles. From the second you drive into the community you feel like you are on vacation. This lower level, 2 bedroom, 2 full bath and bonus room will make you feel right at home. From the wood flooring and full glass sliders overlooking the North East Creek to the large owner's suite and soaking tub and built ins, this condo is all you need either for a primary residence or vacation home. This condo also offers a limited, but year round views and the perfect spot to see the Eagles and Heron that make their home in North East Isles, too! Community amenities include 2 tennis/pickleball courts, pool, boat launch and watercraft storage, fire pit and picnic area and opportunities to rent or buy in the community's private marina. Just an hour from Lancaster, Baltimore and New Jersey. SELLER IS OFFERING A $10,000 SELLER ASSITANCE IF HOME GOES UNDER CONTRACT UNTIL 8/3/2026

113 Ne Isle Dr, North East

Listing courtesy of Integrity Real Estate. Contact:

$1,295,000
3 Beds 4 Baths
Discover unparalleled waterfront living at 1117 Chester Road, nestled in the coveted Long Beach Estates of Middle River. This stunning 2,600+ square foot residence offers three bedrooms and three and a half bathrooms, all set against breathtaking views of Galloway Creek, mere moments from the Chesapeake Bay. Step inside to a dramatic two-story foyer and high ceilings that lead you into a thoughtfully designed living space featuring a cozy gas fireplace. The kitchen shines with elegant quartz countertops and modern appliances, creating a functional and inviting space for everyday living and entertaining. Enjoy seamless indoor-outdoor living with direct access to a spacious deck, ideal for enjoying the serene surroundings. The main level features a luxurious primary suite, offering comfort and privacy. In addition to the finished living area, the home offers approximately 500 square feet of unfinished space with an existing full bathroom, providing exceptional potential for a future recreation room, guest suite, home office, gym, or additional living area. Experience the ultimate in waterfront amenities with your private pier, boasting navigable water, a dedicated boat lift, and a jet ski lift. Additional conveniences include an inviting front porch and an oversized two-car garage. This exceptional property combines elegant design with a vibrant waterside lifestyle. Schedule your private tour today and envision your next chapter.

1117 Chester Rd, Middle River

Listing courtesy of RE/MAX Components. Contact: 4439921983

$1,795,000
3 Beds 2 Baths
A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact: 4102515291

$8,950,000
24 Beds 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971

$320,000
3 Beds 2 Baths
$10,000 Price Reduction – Rare Chesapeake Bay Waterfront Opportunity! Waterfront homes under $325,000 are becoming increasingly difficult to find, making this well-maintained island retreat an exceptional value. Enjoy sweeping western views across the Chesapeake Bay, spectacular sunsets, and the peaceful waterfront lifestyle you've been dreaming of. Ideal as a full-time residence, weekend getaway, or investment property, the home features an updated kitchen with a center island, gas range, coffee bar, and luxury vinyl plank flooring. Flexible living spaces include a first-floor bedroom and office/playroom, an updated bath, a spacious family room, and a private second-floor owner's suite. Additional highlights include ductless mini-split heating and cooling, hot water baseboard heat, high-speed internet availability, rip-rapped shoreline, and a BAT septic system installed in 2019. A county-owned public boat ramp is just down the street beside a privately owned marina where slips may be available for rent (buyer to verify). A brand-new survey and legal description are available upon request. With a $10,000 price reduction, this is one of the best opportunities to own Chesapeake Bay waterfront without the premium price tag.

1814 Hoopersville Rd, Fishing Creek

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

$1,350,000
5 Beds 2 Baths
The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and has invested over $400,000 in improvements across sixty years of devoted stewardship. This property has never been publicly offered for sale — until now. Situated on 1.65 acres with 205 feet of protected waterfront on Cox Creek, this is one of the largest privately held waterfront parcels remaining in Harbor View. The 75-foot private pier extends into navigable tidal water with approximately 3.5 feet at mean low tide and two boat slips. Shoreline reinforced with professional rip-rap. Maps show Flood Zone X — outside 100-year and 500-year floodplains - buyer and agent should verify. The home offers 3,456 sq ft of living space across two levels including 700+ sq ft of unfinished second and third-level expansion space. Five bedrooms, two full baths. The upper-level primary suite features hardwood floors, panoramic water views, attached full bath, walk-in closet, private coffee bar with refrigerator, and a deck overlooking the creek. Updated kitchen with granite countertops, upgraded cabinetry, and high-end appliances, improvements throughout honor the building's barn heritage. Solid block construction. 200-amp electrical. Well water, public sewer. New Roof will be installed prior to settlement. Ideal for those who are seeking genuine Chesapeake waterfront with privacy, deep water access, and a property unlike anything else on the market. Be sure to download the Home Profile in the documents section for more details on the home including the history of the home.

2513 Cecil Dr, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$749,900
3 Beds 3 Baths
Welcome to "Chesapeaks" . a charming weekend retreat nestled above the C&D canal with breathtaking views of the western end of the Chesapeake and Delaware Canal, and beyond towards the head of the Chesapeake Bay. This 2/3 bedroom 2 1/2 bath home invites those hungry souls that seek a natural retreat with abundant wildlife, combined with pleasure boating and the occasional passage of giant commercial marine traffic. Witness the migration of the yachting snowbirds at the change of the season with admiring sunsets that only the head of the Bay can provide. This tranquil property offers the warm charm of natural light in every room. Two pellet stoves add a warming ambiance during the coldest of winter days. Decks galore! Three distinctive decks add more to the "Chesapeaks" experience. One deck attached to the home, another deck serves as a dining platform in the central front yard (remember, this is water front) and the last a multi tiered deck that provides the transition from the home to the boat dock. This is the best place in Cecil County to gaze at the unique sunsets of Chesapeake Bay. Even though this home has a rural "feel" the property is 15 minutes from civilization, including route 95 commuting corridors to Baltimore, Philadelphia and neighboring airports. Be amazed and mesmerized at the boating world and shipping traffic that endlessly passes throughout the summer boating season, and then the quiet splendor of the fall and winter seasons. Enjoy abundant wildlife including deer, eagles, osprey, rabbits, foxes and numerous other mammals. Arrange for your tour today.

64 S Shore Rd, Elkton

Listing courtesy of BHHS Fox & Roach-Christiana. Contact: 3023681621