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$1,690,000
A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,690,000
7 Beds ⋅ 3 Baths
A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$499,000
3 Beds ⋅ 2 Baths
Nestled in the charming West End neighborhood, this stunning Victorian home, originally built in 1920 and beautifully renovated over time, this lovely home offers a perfect blend of historic elegance and modern convenience. With 1,418 square feet of meticulously maintained living space, this detached residence is a true gem. Step inside to discover a warm and inviting interior featuring traditional floor plans that seamlessly connect the living and dining areas. The formal dining room is perfect for hosting gatherings, while the eat-in kitchen boasts upgraded countertops, an island for additional prep space, and recessed lighting that creates a bright and airy atmosphere. The wood flooring throughout adds a touch of sophistication, making every room feel cozy and welcoming. This home features three spacious bedrooms and two full bathrooms, ensuring ample space for relaxation and privacy. The main floor laundry, complete with washer and dryer, adds to the convenience of daily living. Outside, the property shines with its delightful wrap-around porch open to views of the river, as well as the municipal marina. The home also has a rear screened porch, perfect for enjoying morning coffee or evening gatherings. The exterior is enhanced by thoughtful features such as exterior lighting and low maintenance yard fencing. A garage provide additional storage and utility, while the gravel driveway offers off-street parking for two vehicles. One of the standout features of this property is its proximity to the serene Choptank River and Cambridge Creek, just a short walk away the downtown and restaurants. Imagine spending weekends exploring the nearby waterways or enjoying leisurely strolls into town. The neighborhood is rich with local amenities, including parks, shops, and dining options, making it an ideal location for those who appreciate a vibrant community atmosphere. With its captivating views of the creek and river, this home is not just a place to live; it's a lifestyle. Experience the perfect blend of historic charm and modern living in a neighborhood that offers both tranquility and convenience. Don't miss the opportunity to make this exquisite property your own! Some of the exterior photos were AI improved.

102 Vue De Leau St, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$1,495,000
7 Beds ⋅ 5 Baths
McNeil Pointe is a unique, coveted, 2-mile long peninsula of luxury homes. Nestled within the serene enclave of McKeil Pointe, this exquisite 7-bedroom, 5.5-bathroom farmhouse-style residence offers an unparalleled blend of luxury and comfort, set against a backdrop of lush landscapes and tranquil water features. Spanning approximately 5000+/- square feet, this home is a true sanctuary, designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior, where you will find custom, hand-cut walnut floors throughout the open first floor and 2nd floor common areas. The heart of the home is the gourmet kitchen, featuring upgraded countertops, a large island, and top-of-the-line stainless steel appliances, including a six-burner stove and double ovens. The adjoining great room, complete with a cozy gas fireplace, creates an ideal space for gatherings, while the breakfast area invites leisurely mornings with views of the beautifully landscaped surroundings and water. Retreat to the primary suite, a luxurious haven with a bay front window that floods the space with natural light. The en-suite bathroom boasts a jetted tub, walk-in shower, and dual vanities, providing a spa-like experience at home. Each additional bedroom is generously sized, ensuring comfort for all. The exterior consists of 120' of deep, wraparound covered porches, with exposed rafters, beaded ceilings, a standing seam metal roof and stamped stone floors for all-season enjoyment. The remaining exterior of the property is equally impressive, featuring extensive hardscaping, multiple outdoor living spaces including a waterside deck, perfect for alfresco dining or simply soaking in the serene views. The heated in-ground pool offers a refreshing escape on warm days, while the private dock on Fishing Creek provides direct access to water activities such as kayaking, fishing, and swimming. Set on a sprawling 5.7-acre lot, the property is partly wooded and beautifully landscaped, offering privacy and tranquility. The gentle sounds of the nearby pond and the picturesque river views enhance the peaceful ambiance, making this home a true retreat from the hustle and bustle of everyday life. With ample parking, including a gravel driveway accommodating up to four vehicles, and security features, this residence combines luxury with practicality. Experience the exclusive lifestyle that this remarkable property offers, where every detail has been thoughtfully curated for your enjoyment and comfort. Additional features include, but are not limited to 3 zone central air. colonial and solid louvered doors throughout, 6 bedrooms with direct water views, and the 3rd Floor boasts a large Rec room, full bath and two bedrooms with four wide dormers.

5207 Brooks Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$189,900
Rare land offering on Horns Point Road! One of Dorchester County's most sought after neighborhoods - just outside town limits. Tranquil views over fields to the Choptank River. Partially wooded. Health Dept. approved and ready to go! Plans subject to review by the sellers. Lot #5 can be purchased separately for $98,750.

Horns Point Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$98,750
Rare land offering on Horns Point Road! Build on this individual parcel or purchase it together with neighboring Lot #4 (Tax ID# 07-239823 - 2.04+/- acres) for $189,900. Perfect setting for your custom home design. Inquire today for more details!

Horns Point Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$665,000
2 Beds ⋅ 1 Baths
Welcome to Fishing Creek, where Chesapeake Bay waterfront living takes center stage. This beautifully renovated coastal retreat offers approximately 138 feet of water frontage, extensive riprap shoreline protection and incredible views in nearly every direction. Step outside and enjoy an impressive 155-foot private pier with boat lift, jet ski lift, electric, lighting and plumbing, creating the perfect setup for boating, fishing, crabbing and everything the Eastern Shore lifestyle has to offer. Inside, the home has been thoughtfully transformed with an updated kitchen and appliances, renovated tile bathroom, updated flooring, recessed lighting, a gorgeous 200+ sq. ft. sunroom surrounded by windows and water views. Wake up to sunrise over the harbor, unwind with sunsets over the Chesapeake, and enjoy the water from nearly every room. The investment into this property goes far beyond what you can see. Major improvements include a new septic field, extensive riprap shoreline stabilization, upgraded pier infrastructure with boat lift, jet ski lift, updated dock, electric on dock and plumbing, a custom Amish built two-story bunkhouse with insulation, flooring and electric, a 200-amp electrical upgrade, renovated bathroom, new kitchen appliances, waterfront hardscape patio, exterior improvements and a new well pump and many more. These are the big-ticket improvements that deliver true peace of mind. Peaceful, private and built to enjoy the Chesapeake, this is more than a waterfront home. It’s your own Eastern Shore escape.

2530 Hoopers Island Rd, Fishing Creek

Listing courtesy of Keller Williams Flagship. Contact:

$1,800,000
Eastern Shore Waterfront Building Lot. Discover a rare opportunity to own one of the Eastern Shore’s beautiful waterfront lots. Located in the small subdivision of Camelot, this 3.5-acre building lot offers breathtaking sunset views and an exceptional setting to create your dream home. Tucked along Fishing Creek just off the Little Choptank River, the property provides peaceful water views, privacy, and natural beauty. As shown in the photographs, the adjoining property has recently been improved with a newly built home and pier, further enhancing the appeal and potential of this location. Despite its tranquil setting, the lot is conveniently located just a few miles from downtown Cambridge, offering easy access to shopping, dining, entertainment, and local attractions. Whether you envision a primary residence or a weekend retreat, this property offers an unparalleled canvas for your vision and the opportunity to fully embrace the Eastern Shore and Bay lifestyle. Due diligence is recommended for any building lot. Buyers are encouraged to contact the Dorchester County office for information regarding new construction requirements. Permit approved to: Construct a 140-foot long by 6-foot-wide timber pier, a boatlift with associated piles, and two mooring piles extending a maximum of 140 feet channel ward of the mean high-water line. Schedule a tour today - do not enter the property with an appointment or a representative.

5200 Travelers Rest Rd, Cambridge

Listing courtesy of Taylor Properties. Contact:

$649,000
4 Beds ⋅ 3 Baths
Experience the charm of waterfront living with breathtaking sunrise views over Madison Bay. Set on 2.2 acres, this beautifully maintained 4 bedroom, 3 bath home offers approximately 800 feet of rip-rapped shoreline, a private deep-water pier with multiple slips, the perfect blend of comfort and outdoor recreation. The home features a beautifully renovated kitchen with custom cabinetry, quartz countertops, GE Café appliances, brand-new Bosch high-efficiency inverter heat pumps, new luxury vinyl plank flooring and a large waterfront deck perfect for entertaining or simply relaxing while taking in the scenic water views. Additional features include an attached two-car garage, detached garage/storage building, private deep well and county sewer. Enjoy boating, fishing, kayaking, biking and running right outside your door. Located near Blackwater National Wildlife Refuge and public hunting lands, this property is ideal for outdoor enthusiasts and nature lovers. Conveniently located near the Madison public boat ramp, volunteer fire company and just 15 minutes from Route 50 and Cambridge, with shopping, restaurants and Emily's Produce nearby. Whether you are looking for a full-time residence or private waterfront retreat, this property offers the very best of Maryland's Eastern Shore lifestyle. This property would also work very well as an Airbnb. Motivated sellers, offers are welcome.

4825 Madison Canning House Rd, Madison

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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:

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

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$3,200,000
Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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
$575,000
3 Beds ⋅ 2 Baths
Escape to the unspoiled beauty of Hoopers Island, where peaceful waterfront living and world-class fishing, crabbing, and boating are part of everyday life. Situated on a beautifully landscaped 1.06-acre corner lot, this charming 3-bedroom, 2-bath home offers the ideal Eastern Shore retreat with generous indoor and outdoor spaces designed for gathering with family and friends. The heart of the home is a beautifully appointed kitchen featuring granite countertops, abundant cabinetry with under-cabinet lighting, a center island, double wall ovens, gas cooktop, wet bar, and custom wood ceilings. Original pocket doors, warm wood accents, and pellet stoves add timeless character throughout, while the spacious sunroom with skylights and a stone hearth creates a cozy place to unwind year-round. Upstairs offers three bedrooms, a full bath, and a loft that comfortably accommodates additional guests, making this an ideal full-time residence or weekend getaway. Two storage sheds provide ample space for boating and outdoor equipment. Included in the sale is a rare additional 0.13-acre Commercial Maritime waterfront parcel featuring a 100-foot pier with approximately 5 feet of water depth, multiple boat slips, and endless opportunities to enjoy the Chesapeake Bay lifestyle. Whether your passion is offshore fishing, crabbing, kayaking, or simply watching the sunset over the water, this property is ready for your next adventure. Owners also have a duck blind permit with site right off the property for hunter enthusiasts. What more could you ask for? Located just minutes from local favorites including Old Salty's Restaurant, Hoopers Island General Store, and Madhouse Oysters, this exceptional offering combines authentic Eastern Shore charm with the waterfront lifestyle so many dream of—but few ever find.

2404 and 2407 Hoopers Island Rd, Fishing Creek

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

$299,000
3 Beds ⋅ 1 Baths
Welcome to 2517 Old House Point Rd, one of the cutest homes in Fishing Creek. Sitting on elevated ground this three bedroom, one bathroom home has water views from the front and back yard. Large garage you could keep a boat or kayaks and bikes with loft and lean to. Quiet area with relaxing feeling.

2517 Old House Point Rd, Fishing Creek

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$8,950,000
24 Beds ⋅ 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971
$297,000
The most significant hurdle to building on waterfront is permitting for permit septic. This property already has PUBLIC SEWER. This rare offering is 1.8 acres on two combined deeded waterfront parcels situated on the quiet and serine Little Choptank River. Build your dream home or invest. 1609 comes with a current tidewater buffer setback variance (BOA Case #2109), allowing for the construction of a dwelling inside the typical 100-foot setback. Most importantly, this variance does not expire and transfers directly to the new owner, providing a unique "plug and play" opportunity that is nearly impossible to find. Call me today to learn more.

1609 Heliport Rd, Woolford

Listing courtesy of Keller Williams Realty Delmarva. Contact: (410) 524-6400
$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
$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:

$450,000
1 Beds ⋅ 1 Baths
Exceptional opportunity to create your own Eastern Shore waterfront retreat with approximately 6' MLW—a standout feature for sailing enthusiasts and boaters seeking dependable deep-water access. Set in a welcoming waterfront community with a relaxed, laid-back atmosphere, this property offers beautiful water views and an impressive collection of boating amenities, making it an ideal home base for exploring the Chesapeake Bay and surrounding waterways. The private pier is the centerpiece of the property, offering approximately 6 feet of mean low water, a lookout platform, and four boat lifts—including two 1,500-lb jet ski lifts, an 8,000-lb lift, and a 20,000-lb lift installed in 2022. Whether your passion is sailing, power boating, fishing, crabbing, kayaking, or simply spending your days by the water, the infrastructure is already in place to embrace the waterfront lifestyle. The 1-bedroom home is fully ADA-compliant and offers an enclosed waterside porch perfect for relaxing and taking in the view. The renovated full bath features a roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. A wheelchair ramp and lift also convey. Recent improvements include a 50-year architectural shingle roof installed in 2023 with transferable warranty and a new well installed in 2024, along with the convenience of public sewer service. A detached garage/workshop with concrete floors and a newer electrical panel provides excellent space for storage, hobbies, or boating equipment. Plumbing in the workshop is currently disconnected but could be reconnected by the new owner. An additional waterside storage shed near the pier is ideal for kayaks, fishing gear, and outdoor equipment. Bring your vision and make this waterfront property your own. With deep water, substantial boating infrastructure, and beautiful views, this is a unique opportunity to establish a Chesapeake Bay getaway tailored to the way you want to enjoy the water. 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
$669,900
2 Beds ⋅ 2 Baths
Open House Sunday, September 13th 1-3:30. Serving lunch until gone. Seller is offering 6% toward closing with an acceptable offer. Welcome to your private piece of paradise! Not only do you get gorgeous waterfront and sunset views, but you also get a beautiful home and guest cottage. Freshly painted main bath, new thermopane windows, newer roof, meticulous landscaping, and priced to sell quickly! Once you step through the front door, the captivating view through the living room bay window will leave you breathless. Not only is this 2-bedroom, 2-full-bath home well-maintained, but it also sits on over half an acre, giving you plenty of room for entertaining. As much as the intoxicating waterfront views beckon you to your private pier, the house calls you home. Once you walk in, you don't want to leave. This home features a main bedroom with a full bath, a secondary bedroom, a large living room, a beautiful kitchen, and a formal dining room with a breakfast bar, wonderful for holiday entertaining. Spread your party snacks on the bar or use it for extra seating. It has a gorgeous view of the water. The kitchen has plenty of room and is a cook's dream with double wall ovens and a separate stovetop. There is a large pantry for storing your non-perishables. A large guest bathroom, laundry room, and sunroom featuring large windows and sliding glass doors to the patio. This is a remarkable, well-cared-for home that includes a 2-room, full- bath guest cottage for your overnight guests, or use it as an Airbnb. Just imagine yourself out there, entertaining on your huge, over half-acre waterfront lot. Barbecues with family, friends, and neighbors, or fishing and crabbing off your personal pier. Or... picture being out on your boat, pulling off from your private dock, cruising on the water, breeze in your hair, sun shining down. Perhaps you decide on waterfront dining at one of the nearby restaurants, or just a day of fishing. And when the day is done, you either tie back up at your private dock or hoist your boat up using your personal 9,000 lb boat lift. The pier has electricity, water, and a swim ladder. Fish and crab from your private pier. The possibilities of waterfront living are endless. You may decide you want to use this property for year-round living, summer vacationing, or as an Airbnb. You could live in the main house and rent out the guest cottage; the possibilities are endless. There is so much more here; you need to take a look, and perhaps you may see your waterfront homeownership dreams come true. Taylors Island is about 10 minutes away by car; Cambridge is about 20 minutes away for shopping, dining, and more. Low tide mean is 3'.

1514 Deep Point Rd, Woolford

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4105463211
$249,900
2 Beds ⋅ 3 Baths
PRICE IMPROVEMENT! Charming brick end-unit townhome in Riverview Townhouse Condominiums, ideally located just two blocks from downtown Cambridge! Enjoy distant views of the Choptank River, Cambridge Yacht Basin, and iconic Choptank Lighthouse from this beautifully updated home offering the perfect blend of Colonial charm and modern convenience. Recent improvements include new HVAC (2025), windows (2023), water heater, fresh paint, luxury vinyl plank flooring, updated lighting, ceiling fans, and new granite kitchen countertops. The inviting open floor plan seamlessly connects the living and dining areas, making entertaining effortless. The bright kitchen features double windows, recent appliances, freshly painted cabinetry, granite countertops, and updated lighting. Upstairs, both spacious bedrooms feature private en-suite baths with tub/shower combinations and updated vanities, mirrors, and lighting. A convenient stacked washer and dryer complete the second level. Enjoy maintenance-free living with lawn care and trash service included, plus easy access to all that downtown Cambridge has to offer—restaurants, shops, galleries, the art center, marina, waterfront, and the Ironman finish line are all just a short stroll away. Whether you're looking for a full-time residence, weekend retreat, or investment/Airbnb opportunity, this property offers an exceptional combination of location, updates, water views, and convenience. Come see why you may never want to leave!

600-3 Water St, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$998,500
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
$684,900
4 Beds ⋅ 2 Baths
Enjoy waterfront living in this updated 4 bedroom, 2 bath waterfront home with stunning sunrise and sunset views over the Honga River and Chesapeake Bay. Bright and inviting with comfortable living spaces, cathedral ceilings, this home is ideal as a full-time residence, weekend retreat or airbnb investment. The property features a large pole barn with electric and heating & air, shed, large deck and spacious outdoor landing with fire pit overlooking breathtaking Chesapeake Bay views. Located just across from a marina and public boat ramp, you’ll have easy access to boating, fishing and crabbing. Newer well and septic plus a fully riprapped shoreline. Bring your golf cart, kayaks and bikes and enjoy all that Hoopers Island has to offer. Nearby favorites include Old Salty’s Restaurant and Hooper’s Island General Store.

1750 Hoopersville, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$975,000
5 Beds ⋅ 5 Baths
MAJOR PRICE IMPROVEMENT of nearly $225K since first listed- Perfectly positioned on 4.49 private acres at the end of a quiet dead-end road, this stunning property boasts over 2,700 square feet, five bedrooms, and an incredible 1,000 feet of water frontage—creating a rare combination of space, privacy, and panoramic views of coveted Little Choptank River. Designed and built by an architect for their own personal retreat, this one-of-a-kind coastal waterfront sanctuary blends thoughtful design with the natural beauty distinct to the Eastern Shore. Enjoy effortless waterfront living with your own private pier featuring 3’ mean low water, a protected lagoon, and endless opportunities for boating, jet ski'ing, crabbing/fishing, kayaking, and exploring nature abound. Surrounded by wildlife and untouched beauty, this is the kind of setting that feels worlds away—yet you’re just minutes from the charm, dining, and shops of downtown Cambridge. And the opportunities don’t stop there!!--NO HOA and strong Airbnb potential make this not only a dream retreat, but a smart investment just in time for summer.

1307 Broadview Dr, Cambridge

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$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
$799,999
3 Beds ⋅ 2 Baths
SEIZE THE SUNSET! Enjoy waterfront tranquility right at your back door—and don’t miss this significant price improvement! If you’ve been searching for an immaculate, move-in-ready waterfront home with exceptional first-floor living, this may be the one. Major interior renovations were completed in 2022, and this beautifully updated and meticulously maintained 3-bedroom, 2-bath home offers more than 2,300 square feet of bright, inviting living space designed to showcase the beauty of the Eastern Shore. Panoramic waterfront views greet you from nearly every room, with the living room overlooking the breathtaking vistas of Fishing Creek. Two spacious living areas, each featuring a cozy fireplace, provide plenty of room to relax, entertain, and enjoy the changing seasons.The open gourmet kitchen is the heart of the home, featuring custom finishes, modern updates, and a built-in wine cooler—perfect for preparing meals, gathering with friends, or simply enjoying a quiet evening while taking in the view. Major systems and improvements have already been taken care of, offering peace of mind for the next owner. The roof was replaced in 2018, the HVAC system in 2022, and new thermostats were installed in 2024. An updated sprinkler system, new French gutter drains installed in 2025, and an improved Dry-Zone encapsulated crawl space further enhance the home's efficiency and long-term protection. The crawl space also features a new dehumidifier installed on a raised platform, new insulation, and an indoor monitoring system, all completed in 2026. For additional peace of mind, the home includes transferable USAA flood insurance along with annual Dry-Zone, HVAC, and pest control inspection contracts. Connected to public sewer, this home offers the convenience of simplified ownership from day one.Ideally located just a short distance from historic Cambridge and the Hyatt Regency Chesapeake Bay Golf Resort, with easy access to Easton, Oxford, and St. Michaels. Nature lovers will appreciate the close proximity to Blackwater Wildlife Refuge, where you can explore scenic trails, enjoy kayaking and biking, observe abundant wildlife, and perhaps catch a glimpse of the area's magnificent bald eagles. This is more than a home—it’s an opportunity to embrace the peaceful waterfront lifestyle, spectacular sunsets, and timeless charm of Maryland’s Eastern Shore, with the comfort and confidence of a home where many of the major updates have already been completed.

1318 Bell Ln, Woolford

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

$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