Refine Search
Map
Sort by
$624,000
4 Beds ⋅ 3 Baths
Discover the perfect blend of privacy, comfort, and waterfront living with this exceptional move-in-ready Colonial, nestled on 6.01 scenic acres. Offering 4 bedrooms, 3 full baths, and an abundance of versatile living space, this property is ideal as a full-time residence, weekend retreat, or multigenerational home. Wake up to peaceful water views and enjoy your morning coffee on the expansive rear deck overlooking the tranquil setting. Inside, you'll find a spacious country kitchen, a flexible first-floor bedroom or home office, and inviting living areas designed for both everyday living and entertaining. The property is loaded with sought-after amenities, including a private floating dock for boating, fishing, or kayaking, a detached workshop with electricity, heating, and air conditioning perfect for hobbies or storage, and a separate in-law suite complete with its own sauna, providing an ideal space for guests, extended family, or potential rental opportunities. Additional features include a two-car attached garage, an attractive stone walkway with brick front steps, and the peace and privacy that only a rural waterfront setting can provide. Conveniently located just minutes from Cambridge's shopping, restaurants, and schools, while also offering easy access to nearby beaches and major metropolitan areas, this is a rare opportunity to own an affordable waterfront property with acreage, privacy, and exceptional versatility.

5214 David Greene Rd, Cambridge

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$369,900
3 Beds ⋅ 4 Baths
Waterfront living at its best! This home features 3 bedrooms and 3.5 bathrooms which includes 2 primary suites allowing your guests to have an in-suite bathroom. The property also has 2 private decks overlooking the Warwick River and a pier with a recently installed boat lift. This unit was built in 2001 and has a sprinkler system, a large family room with a gas fireplace, new roof and a new boardwalk is being installed soon. The home is in very good condition and ready to move into. Enjoy beautiful sunsets and quick access to the Choptank River and Chesapeake Bay. There are many nearby beaches, restaurants and shopping. This is a must see!!

101 Main - Unit#103 St, Secretary

Listing courtesy of The Glocker Group Realty Results. Contact:

$294,900
3 Beds ⋅ 2 Baths
Coming Soon! Home has been updated: roof with all-new plywood, drywall, electrical, and heat pumps. Inside, enjoy a gorgeous kitchen with granite countertops and stainless steel appliances. Take in the water views from your porch, and enjoy private, off-street parking via the back alleyway. $294,900!

5 Choptank Ave, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$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:

$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
$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
$189,500
Great opportunity to own nearly 8 acres featuring some of the highest and driest ground in Toddville. Located in sought after Sika deer country, this property offers a peaceful rural setting with hunting opportunities, abundant wildlife, and a creek running through the property. The land features a great combination of woods, newly planted pines and natural habitat, creating an ideal setting for Sika deer, wildlife and outdoor recreation. Property offers a working well and newer 4 chamber septic system, adding value and future potential. Also conveying is a 27 ft camper with bump out, providing a great setup for a hunting retreat or weekend getaway. The older home on the property is in need of repairs, including a new roof and is being sold as-is, bring your vision to renovate and bring back to life or tear down and build your own home. Enjoy the privacy, open space and natural beauty of Dorchester County with fishing, boating, public boat ramps and marinas close by.

2551 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$429,900
3 Beds ⋅ 2 Baths
Luxury waterfront living awaits in this updated 3-bedroom (rare) Oakley Beach condo! Enjoy sweeping views of the Choptank River from the deck and a beautifully modernized kitchen featuring sleek quartz countertops ,custom island, and updated cabinet fronts. New LVP flooring. Gas fireplace, Hunter Douglas blinds including insulated, mechanized shade for as much or little view as you want ! Recent HVAC and hot water heater.(2023) Boat enthusiasts will love the included deeded boat slip equipped with a boat lift. Take advantage of fantastic community amenities like the pool, all just steps from your door. Truly worry free and move in ready! Schedule your tour today!

3 Oakley St Unit #202, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$895,000
4 Beds ⋅ 3 Baths
Welcome to 6011 Sunnyside Court...a true destination! This waterfront sanctuary has been completely refreshed with fabulous interior paint and a brand new 30 year roof! It is complimented by a sparkling saltwater pool and wide-open views of the Warwick River -your own resort! Moreover, this property provides great supplemental income for the astute investor. Enjoy the river-front complex when time allows yet rent "the resort" easily while you are otherwise engaged. This listing is unique in that it is sited on land that provides great views of the river which makes it a very popular airbnb property yet no flood insurance is required. It was designed with generously-sized rooms, a beautiful pool side leisure area and ample gardens. In sum, it is a splendidly built, upscale oasis in East New Market. The house is perfectly sited on a spacious 1.2 acre parcel in which to enjoy all seasons. This stylish hide-a-way has it all. Five bedrooms, upscale finishes and room to play. The first floor is fantastic with a wide open floor plan, 2 full bedrooms, a powder room, covered porch and views galore! A gracious living room has French doors overlooking and leading to the pool area. A modern white kitchen has island seating, tons of counterspace and opens to a large dining space with river and pool views. The sunroom has walls of windows and steps to an inviting patio area. The second floor is upscale with room for friends and family. A private primary suite has wonderful views, a stylish bath and great closet space. Two additional bedrooms and bath and laundry complete this light-filled floor. The third floor has great potential with a soaring ceiling and large windows promising future fun! The waterfront pool, inviting patios, riverfront dock and green gardens await your arrival. The saltwater pool is surrounded by a wrought iron fence, secure, yet allows views from all points. The patio has room for games and lounging. Garden areas and game playing lawns are ready for fun. An uncovered pergola and a top of the line dock is ready for your toys and boats. Parking for everyone and the best view in East New Market can be yours! Restaurants and shopping are close by too.

6011 Sunnyside Ct, East New Market

Listing courtesy of Compass. Contact: (410) 429-7425
$399,900
4 Beds ⋅ 4 Baths
Experience resort-style living at an exceptional value in the Residences at River Marsh. Perfectly positioned between the Hyatt Chesapeake Bay Golf Resort, Spa & Marina and the award-winning River Marsh Golf Club, this beautifully maintained 4-bedroom, 3.5-bath townhome offers the ideal blend of waterfront recreation, golf course views, and luxury amenities on Maryland's Eastern Shore. Located just a short stroll from the marina on the Choptank River, boaters will appreciate the opportunity for annual marina memberships with slips available to keep your boat in the water and ready for your next adventure. Golf enthusiasts will enjoy front-row views of the 2nd fairway and 3rd hole from multiple outdoor living spaces, including a ground-level patio, screened porch, and private balcony off the primary suite. Inside, the thoughtfully designed three-level floorplan features hardwood flooring, a spacious center-island kitchen with stainless steel appliances, breakfast bar seating, dining area, and an inviting living room ideal for entertaining family and friends. A front porch overlooking the Hyatt grounds offers glimpses of the marina and resort atmosphere that makes River Marsh one of the Eastern Shore's premier destinations. The upper-level primary suite serves as a private retreat with balcony access, customized California Closets, and an upgraded spa-inspired shower featuring body sprays, handheld wand, and traditional  shower head. Additional custom California Closets throughout the upper-level bedrooms and pantry provide exceptional organization, while updated lighting fixtures add a fresh, sophisticated touch throughout the home. The attached one-car garage provides ample storage for golf clubs, bicycles, boating equipment, beach gear, and everything needed to enjoy the River Marsh lifestyle. Optional memberships are available for golf, community amenities, and select Hyatt resort privileges, allowing owners to tailor their experience to their interests. Enjoy the convenience of walking to the marina, Blue Point Provision Company, golf course, resort amenities, and scenic waterfront trails. Whether you're seeking a full-time residence, weekend getaway, or vacation property, this is an outstanding opportunity to own in one of Cambridge's most desirable resort communities. Best of all, it is currently the best-priced townhome opportunity in River Marsh.

2820 Persimmon Pl Unit #B4, Cambridge

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

$284,999
3 Beds ⋅ 2 Baths
Historic District charm meets everyday convenience at 113 Willis Street. This adorable circa-1916 Victorian sits just down the street from the Choptank River and close to the heart of downtown Cambridge, where you can enjoy local restaurants, shops, parks, marinas, waterfront events, and the character that makes this Eastern Shore town so special. Inside, this three-bedroom home blends classic early 20th-century charm with practical updates, including newer windows, roof, siding, drywall, electrical wiring, and central air, an uncommon and valuable bonus in many historic homes. The welcoming wraparound porch gives the home instant curb appeal, while the fully fenced yard, alley access, off-street parking, and garage/workshop add everyday functionality that is hard to find in this setting. Whether you need storage, hobby space, tools, bikes, or a spot for weekend projects, the garage/workshop gives you flexibility beyond the main house. Cute, comfortable, updated, and full of Cambridge character, this home offers historic charm, modern comfort, and downtown convenience all in one very lovable package.

113 Willis St, Cambridge

Listing courtesy of Keller Williams Flagship. Contact:

$59,999
Nice high elevation building lot on Hoopers Island. Well and septic already in place, includes a newer 4-chamber septic system. Drain fields to be completed once house plans are approved. Great opportunity to build your dream home and enjoy the Hoopers Island lifestyle.

2820 Hoopers Island Rd, Church Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$849,500
3 Beds ⋅ 3 Baths
Price adjustment! Charming custom Cape Cod built by R. Lucas on Church Creek with 150'+/- bulkheaded shoreline, 17K lb. lift and boat ramp perfect for launching kayaks, canoes, etc. The home offers spacious living areas boasting custom built-ins and woodburning fireplace. Just off the family room is access to a hallway with staircase to large unfinished space over the two car garage. Porch to the rear of the house situated to enjoy the tranquil water views. Roof new in 2026 along with other recent upgrades.

4712 Steamboat Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$475,000
1 Beds ⋅ 1 Baths
Exceptional waterfront opportunity with gorgeous water views, deep water access, and extensive boating amenities in a welcoming, waterfront neighborhood known for its friendly and laid-back atmosphere. This fully ADA-compliant 1-bedroom home features a thoughtfully renovated full bath with roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. Relax on the enclosed porch overlooking the water or head outside to the impressive pier offering approximately 6’ MLW, a lookout platform, and four boat lifts including two 1,500lb jet ski lifts, an 8,000lb lift, and a 20,000lb lift installed in 2022—an incredible setup for boating, fishing, and enjoying life on the water. Additional improvements include a new 50-year architectural shingle roof with transferable warranty installed in 2023 and a new well in 2024, plus public sewer service. Wheelchair ramp and lift convey. Detached garage/workshop with concrete floors and newer electric panel offers excellent storage and workspace potential, plumbing in workshop is currently disconnected- but could be hooked up by the new owner. There is an additional storage shed near the pier perfect for kayaks, fishing gear, and outdoor equipment. Bring your personal touches and bring this home to life! Property is being sold as-is. Appointment required for all showings.

5023 Russell Rd, Woolford

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

$629,900
2 Beds ⋅ 2 Baths
Enjoy breathtaking Honga River and Chesapeake Bay views from this exceptional waterfront property featuring a long private pier with multiple slips and two boat lifts. This well-maintained 2 bedroom, 2 full bath home offers comfortable coastal living with a riprapped shoreline, spacious yard and endless opportunities for boating, fishing, crabbing and embracing the Hoopers Island lifestyle. The expansive waterfront deck offers the perfect place to relax, entertain and enjoy cookouts with family and friends while taking in the panoramic waterfront views. Stunning sunrise and sunsets create the ideal setting for a full-time residence, weekend getaway, a peaceful waterfront retreat. Bring your golf cart and bicycles and enjoy nearby local favorites including Old Salty’s Restaurant and Hooper’s Island General Store. Conveniently located within walking distance to a local marina and public boat ramp.

1709 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$367,000
2 Beds ⋅ 2 Baths
WATER VIEWS THROUGHOUT * 1841 sq ft * CORNER CONDOMINIUM HOME * GATED PRIVATE * OPEN CONCEPT * 2 BEDROOMS * 2 FULL BATHS * GARAGE PARKING * 2 ELEVATORS * POOL * PET FRIENDLY* Imagine waking up to water views from every window in your *1841 sq ft* corner condominium home! This gated, private property boasts an open concept, perfect for entertaining. With two bedrooms and two full baths, plus a garage and two elevators, you’ll have plenty of space to enjoy. Plus, it’s pet-friendly! This unit is bright and airy, and you’ll be amazed by the size and volume of the Easton Model floor plan. The 9 ft tall ceilings and lots of large windows fill the space with natural light and offer beautiful views of Cambridge Creek and Trenton St. Marina. The kitchen has a classic, timeless look with stainless appliances, maple cabinetry, and solid surface countertops. The kitchen, which includes a breakfast nook, opens up to the dining, living, and sunroom areas, creating a seamless flow. The sunsets are truly spectacular! This fenced, gated property is secure with security cameras. The condo includes one assigned garage parking spot, plus plenty of overflow parking for you and your guests. Relax and cool off at the onsite pool, pool house with bathrooms and shower amenities, or simply enjoy the sun. The condo is freshly painted in neutral tones, clean, and ready to move in. You’ll also find newer high-traffic laminate flooring and an AC unit with powerful airflow. The energy-saving Aqua Therm combination furnace with a 50-gallon hot water tank system makes heating and cooling efficient. Plus, there’s a convenient locked individual storage room on the main floor. All appliances, including the washer and dryer, are included. This is a second home for the seller, gently used and never rented out. The HOA takes care of the roof, exterior siding, exterior lighting, landscaping, and snow removal. There’s a one-time capitalization fee, a post-settlement fee, and two monthly HOA fees required by the buyer at settlement. This is an outstanding unit, one of the largest available, and a great choice!

700 Cattail Cv Unit #104, Cambridge

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$1,399,000
6 Beds ⋅ 5 Baths
Set on 10 remarkably private acres in Dorchester County’s scenic Neck District, this custom-built waterfront retreat commands sweeping views of the Middle Chesapeake Bay and offers the rare combination of space, comfort, and true Eastern Shore serenity. With over 4,500 sq. ft., 6 bedrooms, 4.5 baths, rip-rapped shoreline, and exceptional indoor and outdoor living spaces, this is a property designed for gathering generations of family and friends. A long private approach welcomes you to a setting where nature and waterfront living take center stage. Inside, hardwood floors, timeless architecture, and expansive Bay views create a warm yet elegant atmosphere. The waterfront family room features a striking stone fireplace with wood-burning insert and opens seamlessly to both the screened porch and covered deck, creating effortless indoor-outdoor living. The spacious kitchen was designed with entertaining in mind, offering a center island, breakfast bar, abundant cabinetry, stainless steel appliances, double wall ovens, pantry storage, and an oversized breakfast room ideal for casual mornings by the water. Formal living and dining rooms provide additional space for hosting holidays and special occasions. The first-floor primary suite serves as a private waterfront sanctuary with direct access to the covered porch and peaceful Chesapeake Bay views. Upstairs, five spacious guest bedrooms and three full baths—including a private en-suite—offer flexibility for large families, guests, or vacation rental potential. Vaulted ceilings and dormer windows add architectural charm and natural light throughout the second level. Outside, the lifestyle only gets better. Spend summer days around the inground pool, rinse off in the outdoor shower after boating or kayaking, enjoy crab feasts on the screened porch, or gather around the waterside fire pit as the sun sets across the Bay. The partially wooded acreage provides exceptional privacy while attracting an abundance of wildlife including bald eagles, deer, ducks, geese, and shorebirds—an everyday reminder of the natural beauty that surrounds you. Located on Ragged Point with Eastern Shore favorites like Soft & Salty Seafood and Danny's Seafood, this property offers easy access to fresh seafood, marinas, boating, and some of the finest fishing and crabbing waters on the Chesapeake Bay. The nearby Neck District Grill is a great spot for breakfast, lunch or weekend dinner. Whether you are searching for a full-time waterfront residence, luxury weekend escape, or investment opportunity with proven vacation rental appeal, this extraordinary property delivers the privacy, waterfront lifestyle, and authentic charm that buyers are seeking on Maryland’s Eastern Shore.

5332 Ragged Point Rd, Cambridge

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

$1,195,000
4 Beds ⋅ 4 Baths
Welcome to a rare Eastern Shore offering where privacy, income potential, and waterfront lifestyle come together on 23± acres along the Little Choptank River. Currently a successful vacation rental, this property presents an exceptional opportunity for a second home that works for you—enjoy it when you want and generate income when you’re away. The expansive acreage provides a peaceful, private setting with endless possibilities—gardening, small-scale farming, hunting, or enhancing the land with an impoundment or pond to attract waterfowl. The waterfront is fully equipped for enjoying life on the water with a partially rip-rapped shoreline, private pier and approximately 2.5 feet of mean low water depth—ideal for boating, fishing, and crabbing, with easy access to Fishing Creek and the Chesapeake Bay beyond. Outdoor living truly shines with an in-ground pool overlooking the water, offering a serene setting for both quiet relaxation and entertaining. The spacious wooden deck provides ample room for dining and gatherings, while taking full advantage of the surrounding views. An outdoor shower adds a practical touch, making it easy to rinse off after time spent on the water or enjoying the outdoors. The 4-bedroom, 3.5-bath residence is designed for comfort and gatherings, offering an open floor plan with two primary suites, each with private baths. The spacious kitchen is a true centerpiece, featuring a large island with breakfast bar, double wall ovens, cooktop, refrigerator, dishwasher, beverage refrigerator, and separate ice maker—fully equipped to handle everything from intimate dinners to large-scale entertaining. The adjacent dining room easily accommodates gatherings, while the family room, just off the kitchen, captures serene water views and opens to a spacious screened porch for seamless indoor-outdoor living. A sunroom adds additional living space, also overlooking the pool and waterfront, creating the perfect spot to unwind year-round. The home’s low-maintenance brick exterior, attached two-car garage with automatic opener, and thoughtful layout make it as practical as it is inviting. Conveniently located approximately 2 hours from Washington, DC and 1.5 hours from Baltimore, this property offers the perfect escape without sacrificing accessibility. Whether you’re seeking a private retreat, an income-producing investment, or a place to fully embrace the Eastern Shore lifestyle—boating, fishing, crabbing, kayaking, paddleboarding, and more—this property delivers. Don’t miss the opportunity to own a truly unique waterfront estate with everything in place for summer enjoyment—schedule your private tour today and start living the lifestyle you’ve been waiting for.

1661 Town Point Rd, Cambridge

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

$1,085,000
4 Beds ⋅ 4 Baths
Exceptional waterfront estate in Dorchester County offers sweeping panoramic views of Church Creek with direct access to the Chesapeake Bay . Also located in the highly sought after Cambridge South Dorchester School District . Featuring over 470 feet of protected shoreline , a private dock with 4 feet of water depth, and a boat lift , this property is a rare opportunity for true waterfront living . The 3400 square foot , two and a half story home is thoughtfully designed to capture stunning water views from every angle . In side you will find four spacious bedrooms , including a grand primary suite , along with two full baths and a half bath on the upper level. The main floor is ideal for both everyday living and entertaining . offering a large waterfront dining room , a cozy water view den , and an expansive living room with a wood burning fireplace . The modern kitchen is beautifully updated and includes a pantry and a covered side porch. A unique extended screened porch off the dining room provides the perfect setting to relax and take in the serene views of Church Creek. Upstairs, the luxurious master suite features walk in closets, and the master bathroom showcases a vintage inspired clawfoot tub , a standout feature for those drawn to a modern farmhouse aesthetic , along side a walk in shower. Step out onto your private deck from the master bedroom to enjoy breathtaking sunsets over the water. Two additional bedrooms share a well appointed bathroom , spacious laundry room includes a new washer and dryer . The third floor offers flexible space with two large rooms , ideal for additional bedrooms , a home office , office gym, or media room . Additional features include multiple outbuildings : a two car garage, a kennel with three bays ready for future fencing , and a separate structure perfect for storage of a office. The property spans three lots totaling 3.395 acres of land , accessed by a long privately owned driveway that ensures ultimate privacy . This truly remarkable waterfront retreat where privacy, natural beauty, and expansive water views come together , an opportunity that must be experienced to be fully appreciated

4928 Gregory Rd, Cambridge

Listing courtesy of Stafford-Stafford Real Estate. Contact: 4103107755
$895,000
Spectacular Waterfront Peninsula – 21.87 Acres in Dorchester County Discover a truly rare opportunity to own a breathtaking 21.87acre waterfront peninsula in Dorchester County, offering unmatched privacy, natural beauty, and over 4,000 feet of protected shoreline. Perfect for boating enthusiasts, the property features 3’ MLW and a 200 foot private pier complete with a boatlift, making water access effortless. This expansive property is fully fenced and equipped with an automatic entrance gate, ensuring both security and seclusion. Additional improvements include small outbuildings, a leanto shed, and the convenience of electric service and running water already onsite—ideal for immediate use or future development. Whether you envision creating a private retreat, recreational haven, or future waterfront estate, this oneofakind property

Condon Rd, Cambridge

Listing courtesy of Shore Living Real Estate. Contact: 4102515291
$325,000
2 Beds ⋅ 3 Baths
Nestled in the waterfront town of Cambridge, this townhouse offers a unique blend of comfort and convenience. With direct access to the Choptank River, enjoy waterfront living right at your doorstep! Waterside deck with electric, water and storage. Primary bedroom balcony with electric and storage. The property also features a boat slip offering boating enthusiasts direct access to the river. Or simply just enjoy the view from your deck. This townhouse is ideally situated near local parks, marinas and great restaurants. Embrace the lifestyle you've always dreamed of in this inviting space.

204 Market Square Unit #12C, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$1,399,999
5 Beds ⋅ 3 Baths
Endless westerly vistas stretch across Madison Bay, delivering breathtaking sunsets that feel like a private showing each and every evening. This is more than a home—it’s a waterfront sanctuary designed for those who expect their lifestyle to be as elevated as their surroundings. Welcome to Saltmarsh, an extraordinary 8.5-acre estate where luxury, privacy, and coastal beauty converge. With 5 bedrooms (plus a bonus room that could be considered a 6th) and 3 full bathrooms, this property effortlessly transitions between an exceptional full-time residence and the ultimate weekend retreat for unforgettable gatherings with friends and family. Spanning over 5,000 square feet, the home is thoughtfully designed to maximize both space and scenery, with walls of windows that flood the interior with natural light and showcase those sweeping bay views from nearly every room. The main level is nothing short of an entertainer’s masterpiece—an open-concept layout anchored by a stunning great room, seamlessly flowing into a chef’s gourmet kitchen and sun-drenched sunroom on one side, while the opposite wing reveals a full-scale game room complete with a pool table and custom bar built for hosting on any scale. Step outside and the experience only gets better. Multiple expansive decks offer the perfect setting for everything from quiet mornings to lively evenings, all framed by panoramic water views. At the private dock, every detail has been accounted for—featuring water and electric, two jet ski lifts, and a 10,000-pound boat lift—creating a true waterfront playground. The oversized 3-bay garage provides ample space for all your water toys, equipment, and more—because a property like this is meant to be enjoyed without compromise. Offered fully furnished, Saltmarsh is completely turnkey—allowing you to step right into an effortless, elevated coastal lifestyle from day one. This is not just a home—it’s a statement.

4808 Saltmarsh Rd, Madison

Listing courtesy of Coldwell Banker Realty. Contact: 4105246111
$1,350,000
4 Beds ⋅ 4 Baths
Welcome to a rare waterfront retreat on Hudson Creek offering 30± acres of privacy, recreation, and breathtaking natural beauty with easy access to the Chesapeake Bay. With over 1,000± linear feet of shoreline and stunning water views throughout, this exceptional property is perfectly suited for boating, fishing, hunting, or simply relaxing and taking in the peaceful surroundings. The property features an extended private pier complete with boat lift, providing direct and convenient water access for all your waterfront activities. A significant bonus is the DU impoundment ideal for waterfowl habitat. The home offers 4 spacious bedrooms and 3 full baths and 1 half bath, designed to accommodate both comfortable everyday living and entertaining. A massive great room and dining area serve as the centerpiece of the home, highlighted by an open balcony that surrounds the space and creates a dramatic, airy feel. Dual stairways provide access to the upper level, adding both functionality and architectural appeal and water views. The eat-in kitchen includes a center island and stainless steel appliances, ideal for gatherings and casual dining. A bright and inviting sun porch offers the perfect place to enjoy morning coffee or unwind while overlooking the water. Additional features include a laundry/utility area, welcoming front porch, and a rear porch that further captures the serene water views. Outside, you’ll find a storage shed and a detached two-car garage, offering ample space for equipment, vehicles, and recreational gear. Whether you’re seeking a private waterfront residence, a weekend escape, or a recreational haven (boating, kayaking, fishing and hunting), this unique property delivers unmatched space, versatility, and waterfront living.

5704 Ross Neck Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$475,000
3 Beds ⋅ 2 Baths
Updated 3-bedroom, 2-bath waterfront home on Hudson Creek offers breathtaking water views. Enjoy crabbing, fishing and boating from your very own Hudson Creek oasis. New 90 ft private pier with 10x20 sun deck and 2 boat slips. Enjoy the large yard, rear screened-in porch, waterside gazebo. Features include a 2-car garage, paved driveway, and ideal spaces for relaxation and entertaining. New well, septic, new kitchen and foyer luxury vinyl flooring. New kitchen countertop, new first floor full bathroom, new front door and fresh paint. Bring your boat and enjoy all pleasures this waterfront home has to offers.

5841 Hudson Wharf Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$2,295,000
4 Beds ⋅ 4 Baths
Set on a 2.38 acre peninsula with 1,100 feet of waterfrontage, 1301 Broadview Drive is a thoughtfully crafted waterfront retreat defined by exceptional materials, timeless detail, and water views from every room. The exterior pairs stone and cedar shingles with copper lanterns and bluestone hardscaping for a classic Eastern Shore look, while inside, custom millwork, mahogany accents, brass floor registers, and a refined mix of designer fixtures and finishes create a warm and elevated feel throughout. The main level is designed for both everyday living and effortless entertaining, centered around an open gourmet kitchen with Shaw fireclay sinks, Waterworks fixtures, marble counters and backsplash, a mahogany island, and a fully integrated appliance suite. A beautifully finished butler’s pantry, breakfast area with custom bench seating, and great room with custom built ins and a gas fireplace with marble surround add both style and function. A dining room, library or office with built ins, powder room, mudroom, and laundry room complete the main level, while the covered deck provides the perfect place to take in the sunset. Upstairs, the private spaces are equally inviting, highlighted by a serene primary suite with a large walk-in closet, private deck, and a spacious marble bath with soaking tub and custom shower. Additional bedrooms offer custom closets, designer lighting, and beautifully finished baths, while a gym and rear upper deck add to the home’s comfort and flexibility. Outside, sweeping views stretch across the Chesapeake Bay, Little Choptank River, and Fishing Creek, with a waterside pool (as-Is) , pier with lift, boat ramp, and detached storage garage completing this exceptional property. Modern conveniences including Nest climate control, security cameras, fiber wiring in most rooms, and smartphone-controlled dimmers add ease to a home where craftsmanship, comfort, and waterfront living come together beautifully.

1301 Broadview Dr, Cambridge

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com
$1,350,000
4 Beds ⋅ 5 Baths
A Private Waterfront Estate Where the World Falls Quiet—and Time Slows to Your Pace... There are homes that offer space. And there are homes that offer escape. At 5419 Ragged Point Road, you leave more than traffic behind—you leave noise, urgency, and compromise. Just a comfortable drive from Washington, D.C., Baltimore, and Ocean City, this contemporary waterfront estate gives you something rare: true privacy without isolation. Set on nearly 12 acres, with an extraordinary 1,500 feet of frontage along the quiet waters of Brooks Creek, this is not simply a home. It is a front-row seat to nature—uninterrupted, unhurried, and entirely your own. Inside, the house speaks in the language of craftsmanship. Four bedrooms. Two full and three half baths. Built in 2007 with a discipline you can feel in every line and finish. And unlike most properties of this caliber, it is offered fully furnished—each piece chosen to complement the home, not merely fill it. The kitchen is not designed to impress—it simply does. Precision appliances from Wolf, Sub-Zero, and Bosch. Everything exactly where it should be, whether you are preparing a quiet dinner for two or hosting a weekend that stretches late into the evening. The primary suite offers a different kind of luxury—the kind that restores you. A deep soaking tub. A separate shower. Silence when you want it. Space when you need it. But it is outside where this property earns its distinction. Step onto one of several balconies or decks, and the view does the work for you. Water in every direction. Light changes by the hour. Mornings that begin with stillness and sunrise and end with beauty that seem almost staged. A private pier extends your living space into the creek, complete with water, electric, and a 12,000 lb boat lift. For boaters, it is effortless. For fishermen, irresistible. For hunters, the presence of a duck blind and abundant wildlife turns the land itself into an asset few properties can claim. And yet, for all its features, the real value of this home is harder to measure. It is the moment you realize you have nowhere else to be. The quiet conversation lasts longer because it can. The feeling—rare, and increasingly valuable—that you have found a place that gives more than it takes. If you’ve been waiting for a property that offers not just waterfront, but a way of living that feels deliberate, private, and complete—this is it. Come see it for yourself. You’ll know very quickly whether it’s simply a beautiful home… or the one you’ve been looking for.

5419 Ragged Point Rd, Cambridge

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

$379,950
3 Beds ⋅ 2 Baths
This thoughtfully designed charming Cape Cod offers coastal living interior and an open and inviting layout. A spacious kitchen flows into the dining and living areas, creating an ideal setting for both everyday living and entertaining. The expansive 36’ x 10’ screened front porch provides the perfect place to relax and enjoy refreshing Bay breezes, breathtaking sunrises, and the area’s renowned sunsets. The primary bedroom is conveniently located on the main level, while the upper-level features two generously sized bedrooms with abundant closet space. There is also an exceptional oversized 3-car garage; measuring approximately 36’ x 35’ - the garage features one bay with an 18’ door, ideal for RV, boat storage, workshop or watersport toys, along with a separate 2-car section providing ample space for vehicles. Ideally situated just a short distance from Old Salty's Restaurant and Hoopers Island General Store, this property offers both tranquility and convenient access to local amenities. Whether you are seeking a full-time residence, weekend getaway, or coastal retreat, this property presents a wonderful opportunity to enjoy Eastern Shore living at its finest. Solar panels are leased; buyer to assume lease subject to transfer approval.

2576 Hoopers Island Rd, Fishing Creek

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$349,900
3 Beds ⋅ 2 Baths
WOW! Seller is motivated and has drastically reduced. Act now while there is plenty of summer left. Chesapeake sunsets and Honga River sunrises. Watermen heading out at dawn. Ospreys, heron, and egrets hunting their dinner. A short walk to crabs harvested that very morning. Everything that makes the Eastern Shore unique -- the Bay, windswept marshes, seafood, its deeply rooted history -- in a magical place where time slows down so you can catch up. Check out the former Airbnb " Hoopers Island Victorian" listing to find out what makes the house and island so special, from the past visitor's reviews. 🏡 The House Cross a breathtaking causeway and you are smack dab in the middle of an island that measures 1/3 of a mile across. this Chesapeake Bay to the west, Honga River to the east, tidal marsh to the north, and a marina to the south. You are surrounded by water and can see it from every room in the house. A spacious Victorian filled with historic details, high ceilings and original hardwood floors. Windows everywhere, all designed to bring in natural light and bay breezes, 3 bedrooms (comfortably sleeps 8), 1.5 baths, all new appliances. 1.4 acres, privacy, outdoor shower, grazing deer and resident Osprey family. Air-conditioning, high-speed internet, 2 fridges. 🔑 Lock and Load All you have to do is move in. Seller has completed extensive renovations. Includes most furniture and lighting, including dining table and chairs, living room couch and chairs, 5 beds, bureaus, TV and 2 refrigerators. Hammock chairs, porch furniture, fishing poles, crab nets and appliances. 🌾 The Island Two miles off Maryland’s Eastern Shore and 45 minutes from historic Cambridge lies Hoopers Island—one of the last inhabited islands in the Chesapeake Bay. Stretching ten miles and made up of three barrier islands, it’s home to pelicans, ospreys, great blue herons, egrets, cormorants, ibis, and only about 500 year‑round residents. Outdoors, the lifestyle truly comes alive--summer firepits under the stars, crisp fall evenings along the shoreline, and kayak adventures just moments way (kayaks included). Each season brings its own rhythm from sun-soaked summer days to the deeply restorative autumn season. 📍 The Region Close to Easton, St. Michaels, and Oxford. Blackwater National Wildlife Refuge offers hiking paths and 17 miles of water trails and a wide variety of local wildlife and scenic views. The Harriet Tubman Museum. a 10-minute drive to Old Salty's Restaurant, an Eastern Shore institution. A 10-minute walk to the freshest crabmeat and steamed crabs. Day trips to Ocean City or Rehoboth Beach, or carve out a half day visit to St Michaels, Oxford or Easton/

1606 Steamboat Wharf Rd, Fishing Creek

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$448,500
4 Beds ⋅ 4 Baths
Back on the market! Due to no fault of the Seller's, you have another chance to make this your home! Welcome to resort-style living at the prestigious Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge, Maryland. This beautifully maintained townhome offers the perfect blend of comfort, convenience, and Eastern Shore charm, located within one of the region’s most sought-after waterfront resort communities along the Choptank River. This 4 Bedroom 3.5 Bathroom home features tasteful upgrades throughout, including maple cabinetry in the kitchen and bathrooms, granite countertops, crown molding, and quality finishes that add warmth and sophistication to the living spaces. Enjoy a balcony on the front of the home offering views of the Choptank River-perfect for morning coffee or evening sunsets. The rear of the home offers three outdoor living spaces, ideal for entertaining, relaxing, or enjoying the peaceful resort surroundings Enjoy a relaxed coastal lifestyle just moments from the award-winning River Marsh Golf Club, marina, spa, waterfront pools, and dining. Whether you’re searching for a primary residence or weekend retreat this property places you in the heart of resort living. Golf, pool, and certain resort amenities may require membership or additional fees.

2830 Persimmon Pl Unit #A5, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$499,900
3 Beds ⋅ 3 Baths
Stunning waterfront views of the Choptank await you at 7 Hatsawap Rd, Cambridge, MD 21613! Imagine unwinding on your multi-level deck soaking in breathtaking sunsets and peaceful water views. This beautifully updated home features three bedrooms and two-and-a-half baths with great Air B&B potential. A welcoming foyer with marble flooring opens to wood floors that extend throughout most of the home. The updated kitchen offers quartz countertops, newer appliances, a convenient breakfast bar, and separate breakfast area. A formal living room with a cozy fireplace, separate dining area, and large family room provide versatile spaces for both everyday living and entertaining. The second floor primary suite is a private retreat featuring a vaulted ceiling, walk-in closet, balcony access with water views, and a charming retro-inspired primary bath full of character. Situated on a desirable corner lot just minutes from the community dock with water access, this property also offers paved parking for added convenience. Close to historic downtown Cambridge, shopping, restaurants, and more! No town taxes and not located in a flood zone.

7 Hatsawap Rd, Cambridge

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