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

2 48th St Unit #1402, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4105247000

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

5209 Al Jones Dr, Shady Side

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$499,900
3 Beds 3 Baths
WATERFRONT OPPORTUNITY!! Rarely does a true waterfront home in the highly desirable Drum Point community become available at this price. Offering 3 bedrooms, 3 full bathrooms, and approximately 2,084 square feet on a scenic 0.28-acre Patuxent River waterfront lot, this home is your chance to create instant equity while designing the waterfront retreat you've always wanted. If you've been waiting for an affordable waterfront property, this is it. The home is structurally full of potential, with much of the work needed being cosmetic updates, rather than a complete rebuild. Bring your vision and transform this hidden gem into a stunning waterfront residence that reflects your own style. With recent renovated waterfront sales approaching or exceeding the $1 million mark, this property presents an exceptional opportunity for homeowners, second-home buyers, or investors alike. Inside, you'll find an open layout with soaring ceilings, expansive windows, multiple living spaces, a bright sunroom, and incredible water views from nearly every main living area. The spacious floor plan offers the perfect foundation for a modern renovation while preserving the home's unique character. Imagine warm hardwood-style flooring, an updated chef's kitchen, beautifully renovated bathrooms, fresh paint, designer lighting, and walls of glass showcasing the river beyond. Step outside and enjoy everything waterfront living is meant to be. Launch your kayak or paddleboard from your own shoreline, spend afternoons fishing or crabbing, relax on the upper-level deck overlooking the Patuxent River, or simply enjoy breathtaking sunsets and abundant wildlife from your backyard. As a resident of Drum Point, you'll also enjoy access to outstanding community amenities including a private sandy beach, boat ramp, fishing pier, playground, picnic pavilion, basketball court, and community events that make this one of Southern Maryland's most sought-after waterfront neighborhoods. Conveniently located just minutes from Solomons Island's restaurants, marinas, shopping, and entertainment, and an easy commute to NAS Patuxent River, this property combines the peaceful waterfront lifestyle with everyday convenience. Finding a 3-bedroom, 3-bath waterfront home for under $550,000 in today's market is almost unheard of. Whether you're looking for a primary residence, vacation home, or investment opportunity, this is your chance to own prime waterfront real estate at an incredible value. With a little vision and cosmetic updating, this home has the potential to become something truly spectacular. Don't miss this rare opportunity—schedule your private showing today before someone else turns this waterfront diamond in the rough into their dream home.

13181 River View Dr, Lusby

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$899,900
3 Beds 5 Baths
**ST. LEONARD CREEK WATERFRONT RETREAT** **Where Every Day Feels Like a Vacation.** Nestled on 2.21 private waterfront acres along the tranquil shores of St. Leonard Creek, this extraordinary retreat offers far more than an exceptional home—it offers a lifestyle centered around nature, comfort, and unforgettable waterfront living. With **4,468 square feet, 3 bedrooms, 4.5 bathrooms, a beautifully finished lower-level recreation room with a full bath that could serve as a 4th bedroom, guest suite, home office, hobby room, or fitness space,** and a detached two-car garage, every space has been thoughtfully designed for relaxing, entertaining, and enjoying the beauty just beyond your windows. Wake each morning to the sound of songbirds, sip coffee as bald eagles glide overhead, and spend your afternoons kayaking peaceful waters right from your backyard. Watch great blue herons stalk the shoreline, turtles bask in the sunshine, deer quietly wander through the trees, and experience the changing seasons from one of the most peaceful settings Southern Maryland has to offer. Inside, expansive Anderson windows and doors blur the line between indoors and out, filling the home with natural light while showcasing breathtaking water views throughout. The chef's kitchen, warm wood accents, multiple fireplaces, and two spacious primary suites create an inviting atmosphere perfect for everyday living or hosting family and friends for long weekends by the water. Whether you're entering a new chapter of life looking for a peaceful waterfront escape or searching for a property that lets you fully embrace kayaking, wildlife photography, fishing, birdwatching, or simply reconnecting with nature, this home delivers an experience that's increasingly difficult to find. As evening settles in, gather around the fire pit beneath a canopy of stars, listen to the gentle sounds of the creek, and end the day exactly as it should be—surrounded by nature, waterfront serenity, and the people you love. This isn't simply waterfront living. It's the lifestyle you've been waiting for.

7440 Sedwick Ct, Saint Leonard

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$1,300,000
3 Beds 2 Baths
Welcome to 783 Sonne Drive, where life on the Chesapeake takes center stage. Perfectly positioned on an elevated waterfront lot just under 1 acre in the sought-after Bon Haven community, this exceptional South River residence offers breathtaking water views and the rare opportunity to embrace the very best of the Chesapeake lifestyle. Designed to maximize its spectacular setting, the home seamlessly blends indoor and outdoor living. Expansive windows fill the interior with natural light, while the wraparound deck creates the perfect backdrop for morning coffee, sunset entertaining, or simply taking in the river's peaceful rhythm. Every day here feels like a vacation. Offering three bedrooms and two full baths, the home presents endless possibilities. Maintain its timeless, traditional character or reimagine the layout with a more open, modern design to suit today's lifestyle. An oversized two-car attached garage provides ample space for parking, storage, and all of your waterfront gear. Step outside to your own private waterfront pier, where boating, kayaking, paddleboarding, fishing, and waterfront entertaining become part of everyday life. With easy access to the Chesapeake Bay, waterfront dining, and historic downtown Annapolis, 783 Sonne Drive offers an exceptional combination of privacy, recreation, and convenience in a very desirable waterfront community.

783 Sonne Dr, Annapolis

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

$277,500
1 Beds 1 Baths
Adorable waterfront 1-bedroom 1-bath condo located bayside in Ocean City, MD! No need to worry about climbing steps, just park and immediately enter into your ground floor residence. Upon arrival you will appreciate the care the current owners took to upgrade and maintain this property. The first thing you will note is the uniform luxury vinyl plank flooring throughout the condo that allows for easy care at the beach! Continue through the bedroom into the bathroom to see upgrades including a new vanity, light fixture, and crab wallpaper that remind you that you are at the beach in Maryland! Back outside of the bathroom the remodeled kitchen will stop you in your tracks. From the stainless-steel appliances to the quartz countertops to the ceramic tile backsplash and the quality soft close cabinets and drawers, you will be impressed! Finally, circle back to the view you saw as soon as you opened the front door, a wide canal sparkling from the sun's rays. The sound of lapping water can be heard from the spacious living by leaving the quality vinyl slider open that also has built in blinds for privacy when needed. The living room features a pull-out sofa with extra comfortable mattress for guests. In addition to one parking spot on the surface lot the condo also has an assigned storage locker on the ground floor for beach items. Make sure to add this condo to your list to see!

512 Robin Dr Unit #3, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$1,250,000
4 Beds 4 Baths
Experience exceptional waterfront living on the beautiful Patuxent River! This stunning ranch-style home offers over 3,300 square feet of thoughtfully designed living space with 4 bedrooms, 4 full bathrooms, and 50 feet of private river frontage complete with a private pier and charming crab shack. Designed for both everyday living and entertaining, the gourmet kitchen features stainless steel appliances, a six-burner commercial-grade range, a butler's pantry, and an open-concept layout that flows seamlessly into the dining area and spacious family room. Elegant shiplap accents, exposed beams, crown molding, and expansive windows frame breathtaking views of the Patuxent River, creating a warm and inviting atmosphere. The main level also features a private in-law suite offering two bedrooms, a full bathroom, a walk-in closet, and laundry room—an ideal setup for multigenerational living, extended family, guests, or a private home office. The luxurious waterfront primary suite, located on the lower level, is a private retreat offering panoramic river views, an oversized walk-in closet, and a cozy gas fireplace. The spa-inspired primary bath features heated floors, a relaxing jetted soaking tub, and luxurious finishes designed for ultimate comfort. Step outside and embrace the waterfront lifestyle. Spend your days boating, fishing, crabbing, or kayaking from your private pier, then unwind in the hot tub or entertain family and friends on the expansive deck while taking in spectacular sunsets. The authentic crab shack adds the perfect touch for enjoying fresh catches and making unforgettable waterfront memories. This exceptional property offers the perfect blend of luxury, comfort, and the unmatched beauty of Chesapeake Bay waterfront living. A rare opportunity to own a private riverfront retreat where every day feels like a vacation.

7737 Patuxent Dr, Saint Leonard

Listing courtesy of Taylor Properties. Contact:

$2,790,000
5 Beds 6 Baths
Welcome to one of Ocean Pines’ most extraordinary waterfront estates, where luxury, recreation, and coastal living come together in a truly one-of-a-kind offering. Situated on a beautifully positioned waterfront homesite with 75 feet of newly bulkheaded shoreline, this remarkable residence encompasses approximately 9,200 square feet of thoughtfully designed living space with 5 bedrooms, 5.5+ baths, and an unmatched collection of resort-style amenities. Designed for entertaining on every level, the home features a spectacular 63-foot indoor pool with a 7-foot depth, private locker room, movie theater, expansive game room with wet bar, sunroom, and an oversized chef’s kitchen that opens seamlessly into light-filled living and dining spaces framed by soaring ceilings and walls of glass overlooking the water. The outdoor living experience is equally impressive. Enjoy expansive waterfront decking, an enclosed brick courtyard with a charcoal grill, multiple spaces for gathering, a rooftop observation deck with panoramic views, and direct boating access from your private dock featuring an 8,000-pound boat lift. Whether hosting family and friends or enjoying a quiet evening overlooking the water, every space has been designed to embrace the coastal lifestyle. Additional highlights include a two-car garage, generous driveway and guest parking, and the home is offered fully furnished (with select exclusions), allowing you to begin enjoying it from day one. Properties of this caliber are exceptionally rare. Whether you’re searching for an extraordinary primary residence, an unforgettable coastal retreat or the ultimate waterfront investment property, 23 Mallard Drive East delivers a lifestyle few properties can match. Schedule your private showing today and discover what life on the water was meant to be!

23 Mallard Dr E, Ocean Pines

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact: (410) 524-0919

$827,500
3 Beds 2 Baths
Live the ultimate West Ocean City waterfront lifestyle in the highly sought-after Cape Isle of Wight community. Situated on an oversized waterfront lot with approximately 80 feet of bulkheaded canal frontage, multiple deeded boat slips, and panoramic bay and canal views, this exceptional property offers quick navigable access to Assawoman Bay, making it a dream for boaters, anglers, and outdoor enthusiasts. Step from your backyard onto your boat for a day of fishing, cruising to waterfront restaurants, exploring the Ocean City Inlet, or relaxing at nearby sandbars, then unwind with breathtaking sunsets from the covered porch or second-level balcony. Inside, this inviting coastal retreat features 3 spacious bedrooms, 2 full bathrooms, an open-concept floor plan, beautiful wood flooring, an updated kitchen with upgraded countertops and modern finishes, and large windows showcasing incredible water views. Designed for waterfront living, the property also offers an attached two-car garage and a detached garage/carriage house ideal for a workshop, studio, hobby space, or additional storage. There's plenty of room for boats, jet skis, kayaks, paddleboards, golf carts, beach gear, and fishing equipment, plus an outdoor shower, oversized yard, and generous outdoor entertaining space. Just minutes from Ocean City's beaches, Boardwalk, marinas, waterfront dining, shopping, championship golf courses, and Assateague Island, this home offers the perfect balance of peaceful waterfront living and convenient access to the best of Maryland's Eastern Shore. Whether you're looking for a primary residence, vacation home, or weekend getaway, this is a rare opportunity to own one of West Ocean City's premier waterfront properties.

12623 Sheffield Rd, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777

$750,000
4 Beds 2 Baths
Welcome to Long Beach Estates in Bowley’s Quarters where every day feels like a getaway. This rare half‑acre sandy‑beach waterfront property showcases sweeping, unobstructed views of Middle River that instantly set the tone for relaxed coastal living. As you arrive, the oversized 2‑car garage and expansive parking pad can accommodate up to six vehicles providing convenience for gatherings and weekend visitors. Step inside and you’re greeted by a bright, beach‑inspired living room that flows into an inviting eat‑in kitchen. Just off the living room, enjoy seamless access to the large screened‑in deck, complete with a hot tub and generous space for entertaining, dining, or simply unwinding outdoors. The main level features two spacious bedrooms, a full bath with laundry, and an impressive waterfront family room wrapped in windows and French doors. This showstopper space delivers panoramic river views that make it the heart of the home. Upstairs, you’ll find two additional bedrooms, including the waterfront primary suite with sliding doors leading to a private second‑story deck perfect for sunrise coffee or peaceful evening breezes. A lower‑level basement offers a waterproofing system and sump pump, providing excellent potential storage. Don’t miss this exceptional waterfront opportunity in one of Bowley’s Quarters’ most desirable locations. Homes with sandy beach frontage and views like this are truly rare.

3815 Middle River Ave, Baltimore

Listing courtesy of Keller Williams Gateway LLC. Contact: (443) 318-8800

$465,000
3 Beds 2 Baths
This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one in the community. Private Pier: Sturdy, deep-water access steps from your back door. New Rip Rap: Fresh shoreline reinforcement ensures long-term erosion protection. Large propane tank which is almost full for newly installed gas log fireplace & furnace. All supporting floor beams in the crawl space have been addressed. Blank Canvas Interior: Down-to-the-studs flexibility ready for your custom layout. Generous Footprint: Over 1,600 square feet of customizable living space facing a waterfront picturesque view. This home will be perfect for the generational waterman looking to be in the Potomac River within just a few minutes or the city resident who is looking to escape for the weekend. Several homes on the street have had a complete overhaul and the home next door is just about completed. Now is your turn to create your waterfront dream!

18800 Mckays Beach Rd, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4432956123

$4,800,000
A once in a lifetime opportunity to own one of Worcester Counties most prestigious and amazingly well cared for farms. 125 acres of direct waterfront. Over 1 mile of waterfront on Ayres/Trappe Creek. This farm has been transformed into something special many will not see in a lifetime. Multiple barns that have been rebuilt and restored to today's modern standards. Approximately 14,000 sq ft. Roads and waterfowl impoundments have been built to Ducks Unlimited standards by the best in the business. Orion Wildlife. Any and all permits are available. 4 acres of Sunflowers are planted each year, protected from the deer by electrical fencing. Massive restoration of all electrical work completed to standard on entire farm including electric and water which has been run to the brand new 6 slip marina. 3 of those slips have new lifts already installed. Brand new never used 8 stall horse barn with pasture area ready to go. Multiple wells all permitted. 7 permitted duck blind sites in the approximate 30 acres of marshland that conveys as a part of this sale. Deep water pond, with dock in a restocked pond ( large mouth, small mouth, bluegill) Private lane, private roads something like this is never offered. No restrictions, no conservation easements. No government programs. Just 125 acres of incredible farmland in immaculate condition. Call listing agent for all showings. Do not enter this farm without representation.

8416 Burbage Rd, Berlin

Listing courtesy of Coldwell Banker/Bud Church Rea. Contact: (410) 524-7888

$495,000
3 Beds 2 Baths
Waterfront on Smith Creek! Just in time for summer fun, this waterfront rambler, with private pier, will have you fishing and crabbing from morning until night. Hardwood flooring greets you upon entering and flows throughout most of the main level. Tilt-out windows and a screened porch ideal for relaxing and enjoying all the sights and sounds of living on the water. New paint and ceiling fans throughout add a fresh new look. All the electric upstairs has been replaced. Roof is 2 years old. Septic is newer to include drain-fields and distribution box. Washer and dryer and well pump are 2-3 years old. The basement is unfinished and a blank canvas to make your own. Situated on a shaded lot with approximately 100 feet of waterfront, the property also features a paved driveway, generous parking, and a handicap-accessible ramp. Tucked away on a quiet dead-end street, yet conveniently located near Webster Field, this all-electric home offers privacy, comfort, and plenty of potential. Come see everything this waterfront property has to offer! Additionally, this home is not in the flood plain.

17248 Gum Landing Rd, Saint Inigoes

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$485,000
2 Beds 1 Baths
Perfect live here year round, and enjoy all the natural beauty of living on the water on Sue Creek. Take time to relax on the deck and watch the Sunsets directly in front. You'll want to stay forever, perhaps take a boatride or row in the calm water. Great home with new Cherry wood kitchen, plenty of cabinet space. Nice dining area, with view to the waterfront. Living room with hardwood floors, and access to the deck. Fully functional lower level has been improved with space for office with built in shelving, and cabinet space. Outside, you'll find the natural secluded deck, with views to the sandy shore, and a walkway, to the water, Launch your Jet Ski, or john boat. Structure of home: Solid 8" Masonry walls to roof peak. Applied insulation and vinyl siding to exterior. Stainless appliances. Existing 80' PIER needs work, but could be replaced, with County Permits as it is " Grandfathered" existing 80 pier. AC unit: Forced-air system; independent duct work from heating system. Located in roof eaves. Electrical: New service upgrade February 2026. 150 AMP with surge protection added. Close to all major waterfront restaurants, Charleys marina & tiki bar, LunaSea, the Middle River Yacht club, Carsons' Creek seafood restaurant. 10 minutes from Middle River. Easy care home, lots of mature plants and trees, landscaping done by Owner, or just put in your Kayak.

2200 Poplar Rd, Baltimore

Listing courtesy of RE/MAX Advantage Realty. Contact:

$3,200,000
5 Beds 6 Baths
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$7,800,000
4 Beds 5 Baths
Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86± acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6± acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5± acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemetery on the west side, dating to the 1700s. Land mix: approximately 60± acres tillable; balance in timber and lawns along the eastern shoreline. Main Residence: Custom-built in 2004, approx. 7,400 sq ft, four en suite bedrooms. Primary suite in the main-floor north wing with private laundry, library, office/workout room, and sunroom. Dramatic great room and dining room with vaulted ceiling, chestnut beams, cedar ceiling, and a raised-hearth stone fireplace. Signature silo feature: 1st and 2nd floors: full baths serving two bedrooms. 3rd floor: window-lined observatory with 360° views across the estate. Wide-plank wood floors milled from the same chestnut as the great room beams. Exceptional craftsmanship throughout; a must-see for discerning buyers. Guest/Farmhouse: Approx. 2,000 sq ft with three bedrooms and one bath. Two wood-burning fireplaces (living room and dining room). Charming and versatile for guests, caretakers, or rental income. Barns and Outbuildings: Large heated barn with concrete floors, three overhead doors, expansive workbench, and open-loft recreation room. Attached a conditioned office/hunters’ lodge with full bath and hookups for laundry and kitchenette. Adjacent irrigated, fenced raised-bed garden; nearby small apple orchard. Additional smaller barn for equipment or livestock. Lifestyle and Possibilities: Ideal for a family compound, equestrian pursuits, or an exclusive retreat. Premier sporting opportunities: shoreline waterfowl, whitetail deer, and turkey. Ample acreage and infrastructure for hobby farming, vineyards, or conservation. A once-in-a-generation opportunity to own an iconic waterfront estate where open water, open sky, and open fields meet. Follow the country road home to the place you belong—Grafton Manour Estate. By appointment only. Do not enter the property by water or land without the listing agent. The property is monitored by camera surveillance 24/7.

22101 Grafton Manour Ln, Wittman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$1,700,000
3 Beds 3 Baths
Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for relaxing, entertaining and enjoying life on the water. Inside, a gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Property is offered as part of an estate and is being sold as is.

104 Myrtle St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$350,000
Discover the endless possibilities with this exceptional 30± acre riverfront property offering a rare combination of natural beauty and investment potential. Zoned for agricultural and commercial use, this versatile tract features a blend of level, cleared land ready for immediate use and wooded acreage that provides privacy, recreation, and scenic appeal. With beautiful river frontage and easy access, this property is ideal for farming, a business venture, a campground or RV park, event venue, recreational retreat, or your future dream home (subject to local regulations). Whether you're looking to expand your agricultural operation, develop a commercial enterprise, or invest in a one-of-a-kind piece of land, this property offers the flexibility and space to bring your vision to life. Don't miss this unique opportunity to own a beautiful stretch of riverfront acreage with unlimited potential!

00 Westernport Rd Sw, Westernport

Listing courtesy of Coldwell Banker Home Town Realty. Contact: 125014.lead@leads.leadrouter.com

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

23145 Edelen Webster Rd, Deal Island

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC. Contact: 4105202600

$885,000
5 Beds 4 Baths
Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$2,840,000
3 Beds 2 Baths
Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

$1,250,000
5 Beds 3 Baths
Discover exceptional waterfront living in this remarkable Selby on the Bay residence, offering approximately 100 feet of Chesapeake Bay shoreline with breathtaking sunrises and panoramic water views. Designed for both comfort and entertaining, this spacious home features a large kitchen with dual sinks and ample workspace, flowing into a bright living area with a cozy propane fireplace. A sun-filled waterfront sunroom opens to an additional family room accented by beautiful knotty pine ceilings, creating multiple inviting gathering spaces. A dramatic spiral staircase leads to the expansive upper level, where a skylight fills the space with natural light. The primary suite serves as a private waterfront retreat, showcasing a wall of windows with stunning bay views. Thoughtful details throughout include built-in shelving, a dedicated office space, programmable Honeywell thermostats, and ceiling fans throughout the home and garage. The main residence offers 5 bedrooms and 3 full baths, providing plenty of room for family and guests. Designed for entertaining, the home includes a wet bar with sink, dishwasher, and beverage refrigerator, while outside, a spacious stone patio overlooks the water, creating the perfect backdrop for gatherings. Beautiful landscaping, paver driveways and walkways, fenced front and rear yards, and an elevated vegetable garden add both charm and functionality. For boating enthusiasts, the waterfront amenities are truly extraordinary, featuring a substantial pier, floating dock, bulkhead, and heavy-duty boat lift with direct Chesapeake access. The oversized boathouse offers protected high-and-dry vessel storage plus ample room for a workshop, maintenance, or additional storage, an increasingly rare waterfront feature. Adding even more versatility, the detached two-car garage includes a separate bonus room with a full bath, ideal as a private guest suite, 6th bedroom, or potential Airbnb opportunity. Located in the sought-after Selby on the Bay community, residents enjoy exclusive amenities including a private clubhouse, sandy beach, playground, basketball and pickleball courts, swimming area, and direct South River access for boating, kayaking, and paddle boarding. Conveniently located near shopping, dining, parks, and trails with easy access to Routes 50 and 97 and just minutes to Annapolis, this is Chesapeake Bay living at its finest.

3689 1st Ave, Edgewater

Listing courtesy of Winning Edge. Contact: 4434636009

$720,000
3 Beds 2 Baths
OPEN HOUSES JULY 11 @ 1-3 PM & JULY 12 @ 11 AM - 1 PM*Welcome home to this charming home in an idyllic setting; a nature lover's paradise on just over an acre of land that abuts Hines Pond; one of largest lots in the neighborhood*Remodeled in 2014, it's a great year-round home or vacation home not more than 60 mins. from Baltimore and not more than 90 mins. from Washington, DC; not too far from Ft. Meade or the Naval Academy either*One-level living inside and out is what so many want today*Open floor plan with remodeled baths and kitchen including stainless appliances, granite counters, and an island large enough for bar seating*Huge primary bedroom with built-in king-size bed and headboard plus built-in entertainment center; walk-in closet; double-sink vanity in ensuite primary bath*Long driveway, garage, carport, and extra parking are perfect for multiple vehicles, family and friends*Bonus "she shed" with electricity!*Magical sunsets from the edge of the pond*1/2 block to private, community beach and tot lot*About 10 min. drive to Ft. Smallwood Park; a little longer to Crosspointe golf and several marinas*Extra bonus is delicious food from local restaurants*Lots of photos because of this amazing home and location!*Please note: water frontage is estimated and Venice on the Bay is a civic association.

7654 Bay St, Pasadena

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

$1,895,000
Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. See potential plans in the pictures and meet the builder to discuss your dream home or bring your own builder. Don't miss your chance to own the last remaining waterfront lot in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle.

48 E Lake Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$875,000
2 Beds 2 Baths
This EXCEPTIONAL 2014 Custom Built Waterfront property in Pasadena Maryland NOW available! Enjoy everything this home has to offer from solid, energy efficient construction to charming designer features to the utmost in outdoor conveniences! With thoughtful planning and design, this home features ICF construction (providing cutting edge Energy Efficiency, Noise Reduction, Safety & Durability), Secure Entryways (for increased energy efficiency), cozy open space layout with beautiful views, excellent flow to outdoor living areas and two primary bedroom suites! From the moment you step under the pergola onto the stone patio feel this home welcoming you, hear the sound of the river calling, see the light reflecting in the refreshing pool THIS, this is home! Entering from the enclosed portico into the foyer notice the quality craftsmanship, designer colors, expert attention to detail. The gourmet kitchen is designed with daily life and entertaining in mind complete with solid surface counters, soapstone sink, range, pantry, wall oven, built-in microwave, mini-fridge for drinks. Notice the port window, hickory island cabinets, the copper bar sink complete with insta-hot. Enjoy meals with a water view and cozy evenings around the wood stove. You will LOVE the big fully screened deck (nice try mosquitos!) complete with ceiling fan/lights and an outdoor kitchen area (propane stove as-is)! The balcony offers another perfect spot to relax with a spectacular view. The masterfully planned primary suite features a media room (convert to a 3rd bedroom??) with pellet stove, a light filled sitting room that walks out onto a covered private stone patio (with views), the spacious bedroom (made private by barn doors) has a 6x12 walk-in closet (built-ins) and dressing area. The spa bathroom has a large jetted soaking tub, walk-in shower, vanity and features heated floors! Conveniently located is the laundry and entrance to the secure storage/utility room (steel door, safe and a fresh air interchange system). A side entrance into the mudroom and lower level suite has a handy sink and additional storage. The spacious upper level bedroom has beautiful views and connects to a full bathroom. Tucked out of sight is a perfect office nook with custom built-in shelving. This property has it all for the outdoor water enthusiast with a .60 acre sloping lot, rare waterfront level space (garden or volleyball?!) a 6' wide private pier complete with party platform and 10k lb boat lift, kayak launch, and the convenience of water & electric at three critical spots! Finished with the river for the day? Cool off in your own private, refreshing waterside in-ground pool outfitted with low chlorine FROG mineral system. The rambling backyard is fully fenced (reinforced to keep pets in and critters out!) Restore the charming 1932 fish pond to add to the charm and magic of this one of a kind property. Mature landscaping and fruit trees are a delight! The oversized 2 car garage features separate 220-volt electric, a lower level walkout storage room, front entry and a convenient side door leading to the gorgeous stone patio shaded by a custom built pergola - a stunning entryway to this spectacular home! Chesapeake schools. Super convenient to Rt 100/97 BWI NSA. There is so much more to this house, be sure to check out the Features Sheet and contact us to schedule your private showing today! Ideally situated at the end of a no-thru street, fortunate will be one to call this gem home!

328 Oakdale Rd, Pasadena

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690

$3,595,000
5 Beds 6 Baths
Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

25610 Chance Farm Ct, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$449,000
Incredible opportunity to own a marina in the village of Ewell on historic Smith Island, Maryland. This recently renovated six slip marina features new construction, with 150 feet bulkhead, three 60-foot deep water docks, a bathhouse, a bait house, and two additional sheds. The marina greets boaters with ample docking space and is perfectly situated between both harbor entrances to the village. Boaters will love the convenience of docking right between two of the islands restaurants and local market. This location, the perfect place for both relaxation and convenience. The property also includes a four bedroom, two bath historic home that requires renovations but could be a vacation rental or primary residence. Call listing agent for more information. Don't miss this rare chance to invest in Island life!

20880 Caleb Jones, Ewell

Listing courtesy of Wilson Realty. Contact: (410) 968-1882