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$599,000
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, 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 stone hearth creates a cozy place to unwind year-round. A private hot tub room, large covered porch, rear deck, fenced yard, and mature shade trees complete the inviting outdoor setting. 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. 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:

$595,000
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: (301) 698-5005
$734,995
3 Beds ⋅ 3 Baths
Welcome to your Chesapeake Bay waterfront retreat, where breathtaking views and thoughtful design come together to create the perfect coastal escape. This beautifully renovated home has been completely transformed with quality finishes while embracing its beach-inspired charm. Wake up to stunning Chesapeake Bay views from the kitchen, living room, primary bedroom, and even the primary bathroom, allowing you to enjoy the beauty of the water throughout the day. Every detail of the renovation was carefully considered, including brand-new luxury vinyl plank flooring, a completely remodeled kitchen, stylishly updated bathrooms, and a brand-new septic system, providing peace of mind for years to come. The home's coastal character is evident from the moment you arrive. Its charming beach-inspired pink exterior perfectly complements the waterfront setting, while the interior continues the relaxed coastal aesthetic with light, airy finishes and custom nautical touches. A one-of-a-kind staircase features rope railings anchored by authentic boat cleats, adding a distinctive maritime element that makes this home truly unforgettable. Whether you're looking for a full-time waterfront residence, a weekend getaway, or an investment opportunity, this exceptional property offers the perfect blend of modern updates, coastal style, and panoramic Chesapeake Bay views. Enjoy spectacular sunrises, the soothing sounds of the water, and the waterfront lifestyle you've always dreamed of—all from the comfort of your own home.

145 Chesapeake Ave, Prince Frederick

Listing courtesy of RE/MAX One. Contact: 4437718009
$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: (302) 539-0800
$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. Additional details and professional photography coming soon.

140 Spa Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$362,000
4 Beds ⋅ 2 Baths
Calling nature lovers; the private Eastern Shore retreat you've been searching for. This potential AIr BnB 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 floore 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.

1511 Crocheron Rd, Bishops Head

Listing courtesy of A Squared Realty. Contact: 804-432-8149
$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:

$595,000
**Confirmed Two (2) Building Rights*** 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: 2372859000
$589,900
2 Beds ⋅ 2 Baths
Experience coastal luxury at its finest in this beautifully updated 11th-floor end-unit condominium in the sought-after oceanfront Antigua building, where breathtaking bay views, unforgettable sunsets, ocean view and direct beach access combine to create the ultimate Ocean City retreat. Lovingly maintained as a private second home, this exceptional residence has been meticulously cared for and is offered fully furnished, making it truly move-in ready. Designed to maximize natural light and panoramic views, the open-concept floor plan features an impressive wall of windows spanning approximately 40 feet across the living room and primary bedroom. The desirable north end-unit location showcases sweeping views of the bay and coastline views while providing a front-row seat to spectacular sunsets, Northside Park's weekly summer fireworks & holiday light displays. The beautifully renovated kitchen is perfect for everyday living and entertaining, featuring KraftMaid cabinetry with pull-out storage, a built-in pantry, granite countertops, a glass tile backsplash, under-cabinet lighting, and new GE stainless steel appliances (2025). A custom dry wine bar with matching cabinetry, granite counters, under-cabinet lighting, and a built-in wine refrigerator creates an ideal space for hosting family and friends. Thoughtful upgrades continue throughout the home with premium COREtec Pro luxury vinyl plank flooring, crown molding, smooth freshly painted ceilings, recessed lighting, upgraded Decora switches and dimmers, six-panel interior doors with matte black Schlage hardware, updated window treatments, and beautifully renovated bathrooms featuring custom tile, Grohe fixtures, Toto toilets, solid glass shower enclosures, and high-end finishes. Additional improvements include a geothermal HVAC system (2017), upgraded electrical panel (2016), new water heater (2024), smart Wi-Fi thermostat, front-loading washer and dryer, and wall-mounted Samsung televisions in both the living room and primary bedroom. The Antigua offers outstanding amenities, including a secure lobby, multiple elevators, on-site management, on-site parking, a newly renovated heated pool, and a completed exterior façade renovation in 2026. Even better, there are no special assessments, providing added peace of mind for the next owner. Ideally located in the heart of midtown Ocean City on 85th St., Antigua places you just moments from popular restaurants, shopping, entertainment, miniature golf, and countless attractions. Enjoy easy access in and out of Ocean City via Route 90, located just a short drive away, while the world-famous Ocean City Boardwalk is only a few miles from your doorstep. Whether you're searching for a luxurious vacation home, a year-round residence, or a turnkey coastal getaway, this exceptional condominium offers the rare combination of premium upgrades, panoramic views, outstanding building amenities, and one of Ocean City's most desirable oceanfront locations. This is coastal living at its very best! See the 3D Virtual Tour!

8500 Coastal Unit #1101, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$1,019,000
4 Beds ⋅ 3 Baths
Steps to the beach and your own private dock, 103 Channel Buoy Road sits canal-front in the heart of Caine Keys II, one of North Ocean City's most coveted waterfront addresses. A private pier and boat dock sit steps from the back door, with the beach directly across the street — two of the Shore's most sought-after features on a single property. Inside, vaulted ceilings, skylights, and walls of glass create a bright, open atmosphere throughout, anchored by a stone gas fireplace in the great room. The kitchen features granite countertops and a full stainless steel appliance suite, and the waterfront deck offers generous space for outdoor living and entertaining. Four bedrooms, three full baths, and 2,248 square feet across a thoughtfully designed layout — no HOA. Major updates completed within the past two years include a new roof, water heater, appliances, pier, carpet, and all-new living room windows. Turnkey, fully furnished, and ready.

103 Channel Buoy Rd, Ocean City

Listing courtesy of Fred Louis Zamer. Contact: 5712498770
$1,595,000
4 Beds ⋅ 3 Baths
Waterfront Home in Terns Landing – Ocean Pines Welcome to this beautiful 4-bedroom, 2.5-bath waterfront home located in the highly sought-after Terns Landing section of Ocean Pines. Designed with an open and airy layout, this home features floor-to-ceiling windows that fill the space with natural light from nearly every angle, creating a bright and inviting atmosphere throughout. The spacious kitchen is highlighted by granite countertops, perfect for both everyday living and entertaining. Just off the main living area, step out onto the extra-large deck overlooking the canal, where you’ll enjoy peaceful water views and stunning vistas of the Isle of Wight Bay. The second-floor loft offers additional living space, ideal for a home office or lounge area, while the generously sized game room provides flexibility and could easily serve as a 5th bedroom. A convenient 2-car garage adds to the home’s functionality. Major updates include a bulkhead less than 10 years old, a brand-new roof (2026), and a new driveway (2025), offering peace of mind for years to come. Enjoy all the benefits of this amenity-rich community, ideal for year-round living or as a second home getaway. With everything Ocean Pines has to offer, this is a rare opportunity you don’t want to miss! This home was built above mean High Tide. Schedule your showing today—this one won’t last long! Property is being Sold “As Is”

24 Stacy Ct, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211
$624,900
3 Beds ⋅ 2 Baths
Welcome to Sunset Beach, where every day feels like a vacation! This beautifully updated waterfront home is move-in ready and offers spectacular panoramic views overlooking Stoney Creek at its intersection with Nabbs Creek. Relax year-round in the heated and cooled sunroom while enjoying breathtaking water views and some of the community's famous sunsets. This is not a drive-by, the interior and views must be seen to be fully appreciated. Boaters will love this incredible location with easy access to Annapolis, the Magothy River, Rock Hall, and Baltimore's Inner Harbor. The community also features a beach and boat ramp on Granada Road, along with a nearby park and playground. Inside, you'll find numerous upgrades including a whole-house UV-C air sanitizer, towel warmer in the primary bath, stamped concrete driveway, and hardwood flooring beneath the luxury vinyl plank flooring. The main level offers approximately 1,590 finished square feet, including the four-season sunroom with its own HVAC system. The finished lower level adds approximately 1,441 square feet and includes a spacious recreation / family room, full bath, workshop, abundant storage, and flexible living space perfect for entertaining or hobbies. Additional storage is available beneath the sunroom for kayaks and other water toys, as well as in the storage shed. There are no mandatory HOA fees; membership in the Sunset Beach Improvement Association is voluntary and provides access to community amenities including the beach, boat ramp, slips, and community area. Low-maintenance living, extensive updates, incredible boating access, and unforgettable waterfront views make this a rare opportunity to own a piece of the Chesapeake lifestyle.

8 Granada Rd, Pasadena

Listing courtesy of Academy Realty Inc.. Contact: (410) 263-9105
$360,000
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: 4105356291
$415,000
3 Beds ⋅ 2 Baths
A rare find—Marwood Manor, built in 1955 by local builder “Woody” Dashiell. Originally his family home, this property has preserved its original character and exceptional craftsmanship, a rarity in today’s market. Conveniently located with easy access to Route 50 and Route 13, it’s a commuter’s dream. Tucked into one of Salisbury’s most desirable neighborhoods, you’ll enjoy the perfect balance of proximity and privacy—just minutes from Downtown, dining, Salisbury University, Tidal Health Hospital, and Pinehurst Elementary School. Set on a double lot backing up to Molasses Creek and connecting to the Wicomico River, this home offers truly standout waterfront living. Fish from your own backyard, canoe or kayak to the river, or launch your boat from the Riverside Boat Ramp less than a mile away. Features include new roof, gutter guards and windows. The charm of this home includes a large sunken den with a wood burning fireplace, formal living room with pocket doors and a gas burning fireplace. The attic has a cedar closet with tons of possibilities along with a large unfinished basement. There are truly so many special spots in this home, a cozy little room off the kitchen open to your ideas a sunroom with French doors leading you to the outdoors and a wonderful view.

609 N Pinehurst Ave, Salisbury

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,700,000
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: 3018622169
$430,000
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: 4106733344
$389,900
3 Beds ⋅ 3 Baths
Welcome to 2069 Case Road, nestled in the tucked-away Waterfront Community of The Village of Bear Creek. This beautifully designed and exceptionally maintained three-bedroom, two-and-a-half-bath end of group townhome showcases thoughtful upgrades and pride of ownership throughout—truly a home designed to be enjoyed for years to come. From the moment you step inside, you’ll appreciate the inviting atmosphere and attention to detail. The main level is filled with natural light and features gleaming hardwood floors, recessed lighting, crown molding, a cozy gas fireplace, a convenient powder room, and a separate dining room perfect for hosting gatherings. The customized gourmet kitchen is both stylish and functional, offering Energy-Efficient stainless steel appliances, granite countertops, an upgraded breakfast bar, and abundant cabinetry—ideal for everyday living and entertaining alike. The adjoining lower deck has a natural gas line-never buy propane again for your grill! The first upper level boasts a spacious and private primary suite complete with a deluxe en-suite bath and a large walk-in closet also has crown molding. Two additional generously sized bedrooms and a full hall bath complete this level. Both bathrooms have Homewerks wi-fi exhaust fans with speakers. The second upper level offers a versatile loft with a wet bar that opens to an exceptional rooftop deck with sweeping views of Bear Creek—an incredible space for relaxing evenings or memorable outdoor entertaining. There is also a natural gas line to the roof deck for either a grill or fire feature. The lower level includes a storage room with rough-in plumbing for a full bath and the potential to convert into a fourth bedroom, a dedicated laundry area, and access to the oversized two-car garage with additional storage space. Residents of The Village of Bear Creek enjoy access to a community pier, with slips available for lease at just $750 per year—perfect for embracing the waterfront lifestyle. One of the Lowest priced slips in the area! Conveniently located near shopping, dining, and entertainment, and just minutes from Canton, Fells Point, Harbor East, and Downtown Baltimore. Easy access to I-95, I-895, and I-695 makes travel to Washington, DC, Philadelphia, New York, and beyond a breeze. This is the lifestyle you’ve been waiting for—make 2069 Case Road your next home!

2069 Case Rd, Baltimore

Listing courtesy of RE/MAX Advantage Realty. Contact:

$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: 3018622169
$625,000
3 Beds ⋅ 2 Baths
Amazing Waterfront 3-Bedroom, 2-Bath Cottage in Ocean Pines Resort! Experience waterfront living at its finest in this charming 3-bedroom, 2-bath cottage featuring an expansive bulkhead with room for both your boat and Jet Skis. Whether you're heading out for a day on the water or enjoying the peaceful views from home, this property offers the perfect coastal lifestyle. The oversized rear deck and spacious backyard create an ideal setting for entertaining family and friends or simply relaxing while taking in the beautiful waterfront scenery. Inside, you'll find an updated custom kitchen complete with granite countertops, stainless steel appliances, and abundant custom cabinetry. Beautiful hardwood floors flow throughout the main level, leading to a spacious living room with a cozy wood-burning fireplace, built-in wood storage, and remarkable water views. The large dining area provides plenty of space for gatherings and is conveniently located adjacent to the kitchen. Step directly from the living room onto the expansive rear deck, where you can dine outdoors, entertain guests, or unwind while enjoying the tranquil waterfront setting. The main level also features a full bathroom, providing added convenience for family and guests. Upstairs features three well-appointed bedrooms, with the primary bedroom showcasing beautiful water views that provide a relaxing backdrop to start and end your day. Additional features include an attached garage and ample parking with a five-car driveway. Ideally located with easy access to the Saint Martin River and Isle of Wight Bay, this home is nestled within the sought-after Ocean Pines Resort community, offering the perfect combination of waterfront living, boating, fishing, and resort-style amenities. Don't miss this opportunity to own a beautiful waterfront retreat with direct water access and exceptional outdoor living. Schedule your private showing today!

32 Driftwood Ln, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4105247000
$1,750,000
9 Beds ⋅ 4 Baths
Experience some of the most captivating views the Chesapeake Bay has to offer. Perfectly positioned at the first exit off the Bay Bridge, this waterfront property showcases sweeping water views, stunning sunrises, and a front-row seat to the iconic Chesapeake Bay Bridge. The shoreline is ideal for enjoying the Bay lifestyle-launch a kayak, paddleboard, jet ski, or small skiff right from your backyard, spend the day fishing or crabbing, and unwind while watching the backdrop of the Bay Bridge. Like new construction this home was built just three years ago, this remarkable home offers 9 bedrooms plus a den, this includes a private 4-bedroom in-law suite with its own full kitchen/laundry and entry perfect for in-laws, guests or even its own apartment. Public water and public sewer provide added convenience, while the location offers easy access to shopping, dining, and everyday amenities without ever having to navigate Route 50. Whether you're seeking a waterfront family compound, vacation getaway, or year-round residence, this property combines modern living, unmatched convenience, and unforgettable Chesapeake Bay views. Lot next door is included in sale giving home just under 1 acre.

410 Wallman Way, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$525,000
3 Beds ⋅ 3 Baths
Timberloft #7 is an affordable fully furnished three bedroom two and a half bath three story townhome with a deeded boat slip and lift. Pull into your carport and hop right onto your boat, you deserve it! Lots of storage areas for all your water toys and beach chairs. Walk up to your main floor to your upgraded kitchen with granite counters, SS appliances and comfy living room with waterfront deck. You also have a convenient half bath on this floor. Next level includes two bedrooms both with custom closet design and one full bathroom. Top floor is a spacious loft with lots of sleeping areas and an additional full bathroom, some neighbors have converted this great space into a roomy second primary suite. Windows, sliders have also been replaced and HVAC & hot water heater only 4'ish years old and also has built in sprinkler system. Timberloft is a great self managed boating community walking distance to the beach. Bonus.. two parking spots, one covered. It's your time to finally get that vacation home you've always dreamed of and capitalize on some rental income too as there are no rental restrictions!

124 Newport Bay Dr Unit #7, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC. Contact: 4105202600
$1,000,000
3 Beds ⋅ 3 Baths
Come see this home and begin dreaming to make it your own custom waterfront retreat. Welcome to the sought-after waterfront community of Loch Haven Beach! Nestled along the South River, 3440 South River Terrace offers expansive water views and an exceptional opportunity to enjoy a waterfront lifestyle. Visit the Loch Haven community website to learn more about this historic waterfront neighborhood and its many amenities. The Loch Haven Civic Association owns the waterfront property extending from the lot to the water's edge. The pier is part of the Pier 11 Club and is not privately owned by the seller. A significant benefit to the new owner is that no voluntary buy-in is required for Pier 11 membership, as the annual $105 pier assessment is included in the property's tax bill. The pier is maintained by the Pier 11 Club. Enjoy an active waterfront community with neighborhood traditions including the annual Fourth of July parade, food truck events, and the beloved Lochtober Fest each fall.

3440 South River Ter, Edgewater

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$345,000
1 Beds ⋅ 1 Baths
The BEST 1-Bedroom in Bradley on the Bay — This Is It! This is the one you’ve been waiting for — the ONLY unit in the entire Bradley on the Bay community with an extra-large deck right over the bay. Completely updated in the last few years with new windows, a refreshed bathroom, and a modern kitchen. Move-in ready and clearly a cut above the rest. The best mid-town location within walking distance to all the hot spots. Coconuts, Shottis, Jolly Rogers, and more. Enjoy bayside living at its finest with community amenities including a bayfront pool, sandy beach area, boat slips, and kayak/paddleboard storage — all just steps from your door. Grab the best before it’s gone.

3701 Coastal Hwy Unit #324F, Ocean City

Listing courtesy of Engel & Volkers Ocean City. Contact: (443) 292-6767
$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: 4438562211
$1,375,000
3 Beds ⋅ 4 Baths
Set on Cypress Creek in desirable Severna Park, you’ll find a rare combination: deep-water private pier and a 3-bedroom, 3.5-bath home with top-to-bottom modern updates. The flow of the home is excellent, with the kitchen strategically placed between the cozy living room and spacious great room. You’ll love the gorgeous, wide-plank hardwood floors throughout the entire main floor. Step out to the screened porch in the warmer months or gather by the fireplace in the winter. There are two bedrooms and two fully renovated bathrooms in addition to the primary suite. The primary suite includes a huge walk-in closet (former 4th small bedroom!), and new bathroom. The walk-out lower level offers a rec room, overflow bedroom or craft room, laundry and half bath. There is also an optional laundry hook-up on the main level. Inside and out, one can just start enjoying the waterfront lifestyle. A major 2023 renovation modernized the home, including new siding, and created a splendid great room with adjoining waterside screened porch. The same year, there was a full HVAC overhaul: a new heat pump, air handler, and two energy-efficient mini-splits for zoned, year-round comfort. New spray-foam insulation across the full attic (2026) keeps the home tight and efficient, and updated retaining walls (2022) and composite decking mean low-maintenance outdoor living for years to come. Note that the roof is just 10 years old, and the 8,000 lb boat lift is 7 years old. The private dock was dredged to 5' MLW (2019) on the sailboat side, providing a clear, navigable run straight to the main channel — a meaningful advantage for anything beyond a small craft. You’ll easily be out to the Magothy and the Chesapeake Bay beyond. The fully fenced grounds — including a driveway gate — offer privacy and security, while the detached office with wall-to-wall radiant heated floors (and mini-split) makes working from home a genuine pleasure. Add a treehouse, an adjustable in-ground basketball hoop with a glass backboard, and oversized lofted garage storage, and you have a property that works as hard for play as it does for everyday life. Cypress Creek is a water-privileged neighborhood that offers quick access to Severna Park schools and shopping.

718 Dill Rd, Severna Park

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

$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: (302) 539-0800
$675,000
4 Beds ⋅ 3 Baths
Please view the Fly-Through Video! Remarkable Wicomico River Waterfront Home! Please view the Fly-Through Video! Kick back and relax Chesapeake style and fulfill your coastal dreams in this elevated 4 bedroom, 3 full bath home on 3.3 scenic acres, with more than 240 feet of waterfront. Enjoy water views from all but one room in the house and soak up the sun and breathtaking sunsets from the upstairs and downstairs covered porches. The River View Acres Community, comprised of only four homes, share a common dock complete with water and electric. Each home conveys with a deeded slip. In addition, this home conveys with two lifts, a 12,500 lb. remote controlled lift and a small lift appropriate for a jet ski, john boat, or kayak. This home offers paradise for the boater, fisherman, crabber, waterfowler, photographer, gardener, writer, artist, bird enthusiast, and nature lover. The river never disappoints! Inside the home, the discriminating chef surely will enjoy cooking from the island, which overlooks the river. A separate drinks/appetizer bar allows guests to interact with the chef, but not interfere with the cooking. The 2015 custom cabinetry, granite countertops, and stainless steel appliances, offer ample room for food prep and culinary tools. Two bedrooms downstairs share a full bathroom while the upstairs boasts two very large en suite bedrooms. The master bedroom has two French doors that lead to a covered porch that overlooks the river. It also includes a large closet that includes the washer (2024) and dryer. The master bath has a Jacuzzi and double shower. Other home updates include a new roof (2017), new hot water heater (2022,) dishwasher (2022), and baths (2017). Underneath the house is a large enclosed workshop for tools and equipment. There is plenty of parking for cars, trucks, boats, and tractors. Abundant cozy light fills this home, located minutes from the historic White Haven Ferry, historic Princess Anne (with grocery store, shops, and restaurants), and Salisbury. A 10-minute boat cruise up river leads to the Wicomico Yacht Club and Bordeleau Winery. A short cruise down river leads to the Chesapeake Bay. The nearby Salisbury Airport offers direct flights to Orlando and Charlotte, among other places. Atlantic Ocean beaches are a 45-60 minute drive away. Large metropolitan areas are 2 - 4 hours away. Change your pace, breathe deeply, enjoy Chesapeake life, and enjoy this home!

13460 Harrison Landing Rd, Princess Anne

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$299,500
2 Beds ⋅ 2 Baths
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 country side 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 is must see to be appreciated.

27174 Champ Wharf Rd Champ Wharf Unit #27174, Princess Anne

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4105247000
$3,100,000
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: 4106733344
$519,900
3 Beds ⋅ 3 Baths
Wake up to breathtaking water views at 737 Shore Drive in Joppa! This beautifully renovated waterfront home offers a rare opportunity to enjoy the best of coastal living while benefiting from modern updates and improvements throughout. From the moment you arrive, you'll be captivated by the property's scenic setting and stunning water views that create a peaceful, resort-like atmosphere. Whether you're enjoying your morning coffee overlooking the water, hosting friends and family, or unwinding at the end of the day, the picturesque surroundings provide an exceptional backdrop for everyday living. Inside, the home has been thoughtfully renovated to blend modern comfort with timeless charm. Updated finishes, refreshed living spaces, and abundant natural light create a welcoming environment designed for both relaxation and entertaining. Large windows help bring the outdoors in, allowing you to enjoy the beauty of the water from the comfort of your home. Step outside and embrace the waterfront lifestyle with opportunities for boating, fishing, kayaking, or simply taking in the serene views. Conveniently located near shopping, dining, and major commuter routes, this property offers the perfect balance of tranquility and accessibility. Renovated waterfront homes with views like these are a rare find. Don't miss your chance to own this exceptional property and enjoy waterfront living at its finest.

737 Shore Dr, Joppa

Listing courtesy of Witz Realty, LLC. Contact: