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$299,000
3 Beds ⋅ 3 Baths
Welcome to this charming farmette featuring a 3 bedroom, 2 3/4 bath home that has been elevated and features a conditioned crawl space, includes a 3-stall barn, pole barn and shop/shed. Situated on over 8.5 acres, this property offers open fields, established pastures with fencing, a pond and wooded areas, creating the perfect blend of recreation, hobby farming and peaceful country living for the nature enthusiast and hunters alike. Enjoy Sika deer and waterfowl hunting right in your own backyard, with endless opportunities to enjoy the outdoors. Nearby marinas and public boat ramps provide convenient access for boating, fishing and crabbing.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$199,000
One of a kind nearly 22+/- acre recreational property offering an exceptional setting for the outdoor enthusiast. Partially wooded with established trails, open fields and Farm Creek water frontage, the property offers excellent opportunities for Sika deer, goose and duck hunting. Nearby marinas and public boat ramps provide convenient access for boating, fishing and crabbing. Whether you're looking for a private hunting retreat or simply a place to enjoy the Eastern Shore outdoors, this unique property offers endless recreational opportunities. This property is accessible from Toddville Road, providing easy, private access.

Sika Deer & Waterfowl Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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
$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
$699,000
4 Beds ⋅ 3 Baths
This custom-built 4 bedroom home on over 3.5 acres in Heron Harbor perfectly blends elegance and luxury with coastal charm and comfort! With a private community pier and dock on Fishing Creek, homes like this are seldom available but this 2019 Charles " Wiggs" Brohawn custom dream home can be yours for under $700K! The floor plan is designed for both sophistication and livability...access formal living and office space with crown molding and 9'+ ceilings from the foyer, relax with family and friends in the open kitchen and great room at the back of the main level with a gas fireplace and screened rear porch. The gourmet Kitchen features quartz countertops, a 5 burner gas cooktop, double wall oven, large island, and stainless appliances. A large Butler's Pantry with wet bar and wine storage provides additional storage beyond the extensive custom cabinetry. In addition to the island seating, enjoy meals in the bright and sunny dining space. Enjoy the rear screened porch with ceiling fan during three seasons and the inviting gas fireplace in the expansive great room during the winter months. At the top of the stairs, guests can enjoy a large flex-space to the right while the private bedrooms are accessed to the left. The spacious primary bedroom has 2 walk-in closets and a luxurious en-suite bathroom with an oversized tile walk-in shower with seat and multiple shower head as well as dual vanities. A large central atrium connects the primary to the 3 additional large bedrooms, laundry room, and bathroom with dual vanities and tub-shower along with pull-down attic access. In addition to the stunning interior, enjoy the charm of the welcoming front porch, the convenience of an oversized 2 car garage, and the beauty & privacy of the wooded 3.73 acres. Come see all that this property and community have to offer at our Open House on 9/12! Home is owner-occupied so please don't access property/driveway without an approved showing appointment; all buyers and their agents to complete due diligence regarding property taxes, zoning, measurements school, HOA, insurance, and other property information. Schedule your tour today!

5230 Heron Rd, Cambridge

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$399,000
5 Beds ⋅ 4 Baths
Welcome to 16 Buena Vista Avenue! This very spacious 5 bedroom, 3.5 bath brick rancher is situated on an attractive corner lot in the sought-after, quiet Algonquin neighborhood, within walking distance of Sandy Hill Elementary School. The home offers generous living spaces, a brick fireplace and lots of natural light. A large detached outbuilding features an oversized two-car garage with a spacious bonus recreation room, offering excellent space for entertaining, hobbies and additional storage. Conveniently located near the waterfront, with a nearby marina offering boat slips for rent, as well as shopping, dining, and easy access to Route 50.

16 Buena Vista Ave, Cambridge

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to Crump Point, an extraordinary renovated waterfront sanctuary nestled on approximately 5± private acres overlooking the tranquil waters of Church Creek. Offering exceptional privacy and captivating panoramic views, this remarkable property captures the essence of Eastern Shore waterfront living. Thoughtfully designed to embrace its breathtaking surroundings, the 3-bedroom, 2.5-bath residence offers stunning water views from nearly every room. The main level is anchored by a spacious gourmet kitchen featuring an oversized island, creating the perfect space for entertaining or gathering with family while enjoying the picturesque waterfront backdrop. All new stainless steel appliances throughout. The first-floor primary suite provides a private retreat complete with serene waters views, waterside deck, walk-in closet, walk-in shower, and oval soaking tub. Outdoor living is equally impressive with a spacious waterfront deck, screened waterside porch, and an upper-level waterside deck—ideal for morning coffee, evening sunsets, or simply taking in the ever-changing beauty of Church Creek. A private pier offers direct access to the water for boating, kayaking, fishing, and crabbing, while the beautifully landscaped grounds provide ample room to enjoy the peaceful surroundings. Additional features include a circular driveway, attached two-car garage, first-floor split-unit heating and cooling, and second-floor central air with baseboard heat. Whether you’re seeking a full-time residence or a weekend waterfront escape, Crump Point offers a rare opportunity to own an exceptional Eastern Shore property where privacy, natural beauty, and timeless waterfront living come together in perfect harmony.

1619 Perseus Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$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
$299,000
3 Beds ⋅ 2 Baths
Beautifully renovated and move-in ready, this furnished 3-bedroom, 2-full-bath home is nestled in the heart of Sika deer country. The home is in excellent condition and features beautiful hardwood and luxury vinyl plank flooring, central heating and air, mini-splits, a pellet stove, and a detached one-car garage with a finished bonus room above, complete with electric and a mini-split for heating and air. Outside, enjoy a storage shed, fire pit, established orchard with pin oak, apple and persimmon trees, and a deer feeder that conveys. The nearby public boat ramp and marina provide easy access to the Honga River. Whether you're looking for a full-time residence, weekend getaway or hunting retreat, this turnkey property is ready to enjoy. Backs up to a 350+ acre managed Sika deer/farm property. *A new septic system is scheduled to be installed within the next 30-60 days. The existing system is functioning; however, replacement was recommended following a recent inspection, and the seller is moving forward with installation.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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
$439,900
3 Beds ⋅ 2 Baths
Whether you're dreaming of a peaceful country lifestyle or ready to bring your horses home, this picturesque farmette on nearly 5.5 acres is ready for you. The property is already set up with established pastures, a barn featuring four stalls and a feed room and plenty of space for horses and other animals. The updated 3 bedroom, 2 full bath farmhouse blends modern updates with timeless charm and features newer mini-split heating and cooling systems, a cozy pellet stove and a convenient first-floor primary bedroom. A detached two car garage includes a 1 bedroom, 1 bath apartment above, ideal for guests, extended family, rental income, or a private home office.

5125 Rhodesdale Rd, Rhodesdale

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$129,900
2 Beds ⋅ 1 Baths
Escape to your own private retreat with this 5.02-acre property located just minutes from the renowned Blackwater National Wildlife Refuge. Featuring a 2-bedroom, 1-bath home, this fixer-upper offers an excellent opportunity to renovate, invest, or create the hunting cabin or private retreat you’ve always wanted. Surrounded by some of Maryland’s premier outdoor recreation, the property is ideally situated for hunters and nature enthusiasts. Enjoy outstanding opportunities for sika deer, whitetail deer, and wild turkey hunting, with Blackwater National Wildlife Refuge and thousands of acres of nearby public lands helping make this a destination for wildlife and outdoor adventure. Nearby marinas and public boat ramps provide excellent opportunities for boating, fishing, and crabbing. Whether you���re looking for a weekend getaway, recreational property, or a project with ample potential, this property offers the perfect combination of privacy, acreage, and an exceptional location. Bring your vision and make this Eastern Shore property your own. Property sold as-is.

2439 Asquith Island Rd, Crapo

Listing courtesy of Iron Valley Real Estate Crossroads. Contact: 2403979292
$167,900
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 features a brand new complete 4 chamber septic system (never used), adding value and future potential, existing well. 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
$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
$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
$45,000
Last remaining building lot in desirable Cattail Crossing! This level homesite offers a great opportunity to build your dream home in an established, well-kept community with amenities, just minutes from downtown Cambridge. Seller has decided to go in a different direction, creating an excellent opportunity for the next owner. Public water and sewer hookup available at the lot, making for an easy build process. Enjoy a peaceful setting situated on quiet cul-de-sac with convenient access to marinas, shopping, and restaurants.

112 Audubon Ct, Cambridge

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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
$25,000
Attention hunters, anglers, and outdoor enthusiasts! Escape to Hoopers Island and claim your own private base camp in one of the Chesapeake Bay’s most sought-after fishing and hunting destinations. This water-view lot offers the perfect setting to unwind, recharge, and enjoy the best of Maryland’s Eastern Shore. The property includes two storage sheds—ideal for stowing boats, gear, decoys, and everything you need for your next adventure. Take in scenic views of the Chesapeake Bay and experience the peace and quiet that make island living so special. Conveniently located just minutes from Old Salty's Restaurant and a short drive to Blackwater National Wildlife Refuge, you’ll have easy access to some of the region’s premier hunting grounds and world-class fishing waters. Public boat ramps and marinas are nearby, making it simple to get out on the Bay whenever the mood strikes. Whether you're casting for rockfish at sunrise or setting up for waterfowl season, this property puts you right in the heart of it all.

2125 Hoopersville Rd, Fishing Creek

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$1,795,000
4 Beds ⋅ 3 Baths
Fabulous waterfront home with modern flair and a stunning indoor pool, ideally located in McKeil Point, offering effortless one-level living and an open floor plan designed to capture spectacular, unobstructed water views from nearly every room. The thoughtfully designed split-bedroom layout ensures privacy, featuring a serene primary suite with direct access to the indoor pool, a luxurious bath, and a private waterside deck. The spacious kitchen includes a center island with bar seating and flows seamlessly into a separate dining room, perfect for entertaining. A light-filled family room opens to both the indoor pool and expansive waterside deck, creating the ultimate indoor-outdoor lifestyle. Set on over 6 acres along scenic Fishing Creek, the property boasts a rip-rapped shoreline, private pier and boardwalk, abundant wildlife, and a two-car side-loading garage, offering a rare blend of tranquility, space, and waterfront living at its finest with the advantage as a valued vacation rental destination.

5227 Brooks Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$650,000
4 Beds ⋅ 3 Baths
MAJOR PRICE REDUCTION! A rare opportunity to own a private waterfront retreat that not only offers an exceptional Eastern Shore lifestyle, but also a proven income-producing investment — with over $46,000 in rental payouts over the past two years and an active upcoming reservation calendar, the next owner can enjoy immediate revenue while still reserving time for personal use. Escape the pace of city life and discover your own secluded waterfront sanctuary on St. John's Creek, nestled among 3.5 picturesque acres. Conveniently located within an easy drive of Baltimore, Washington, D.C., and Northern Virginia, this peaceful retreat is surrounded by the natural beauty of Maryland's Eastern Shore, where bald eagles, osprey, herons, ducks, geese, sika deer, and other wildlife are part of everyday life. The charming cottage is filled with warmth and character, offering a welcoming living room with a mantle and pellet stove, a cozy kitchen and dining area, a versatile first-floor bedroom, laundry room with daybed, and a full bath. Upstairs, a spacious bedroom with a half bath and wood stove creates a peaceful, storybook-like retreat. The brick-floored screened porch overlooks St. John's Creek and the private pier, providing the perfect setting for morning coffee, evening cocktails, or simply watching boats and wildlife pass by. Designed for gathering family and friends, the thoughtfully crafted carriage house (guest house/second dwelling) significantly expands the property's versatility. It features a spacious bunk room with six bunk beds, an oversized second-floor bedroom accommodating two queen beds, plus a main level with kitchen, dining area, living room, and full bath. An attached two-car barn-style garage provides additional storage and functionality. Between the cottage and carriage house, the property comfortably sleeps up to 15 overnight guests. Offered fully furnished and completely turnkey, the property is ready to enjoy from day one. Relax around the waterside fire pit, launch kayaks and paddleboards from your private pier, or dine just minutes away at the popular Boats & Hose Restaurant. Due to the property's active vacation rental schedule, showing availability is limited — a comprehensive virtual tour will be available soon, allowing prospective buyers to experience the property while private showings are accommodated around existing guest reservations. Whether you're looking for a private waterfront getaway, a full-time residence, or an investment with established income potential, this property offers the flexibility to do it all. This is a rare opportunity to purchase a turnkey waterfront property with immediate income already in place.

4004 Robinson Neck Rd, Taylors Island

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

$99,900
3 Beds ⋅ 1 Baths
Affordable 3 Bedroom, 1 Bathroom home conveniently located in Toddville and includes the vacant land parcel across the street (Parcel 164). Previously rented as a hunting lodge, good for overnights, a casual retreat or full time living. Located across from Elijah’s General Store and near public boat ramps, Blackwater national wildlife refuge and marinas. Enjoy fishing, crabbing, hunting, biking, and boating.

2703 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$625,000
3 Beds ⋅ 2 Baths
Situated as the last privately owned property on Maple Dam Road before entering Blackwater National Wildlife Refuge, this 10.54± acre offering occupies an exceptional setting surrounded by refuge lands on all sides. The property lies within thousands of acres of permanently protected public ground, providing unmatched privacy, wildlife presence, and long-term landscape preservation in the heart of Dorchester County. Improvements include a 1,718± square-foot residence powered by a PV solar array, backed by an on-demand 22kw generator delivering efficient and sustainable energy. Climate control is handled by six mini-split systems, with an additional in-box unit conveying with the sale, offering flexibility for future expansion or replacement. The home features two gas fireplaces, with one having an option to burn wood, adding both comfort and versatility. A four-person hot tub is included, creating an ideal space to unwind and watch the sunset. A 30’ x 30’ garage with 14-foot ceilings provides ample room for boats, equipment, and sporting gear. in addition to the large garage, a climate-controlled office/workshop is just steps away from the main house. The land itself is highlighted by natural marsh ponds and wetlands, enhancing habitat and contributing to the area’s outstanding waterfowl hunting and well-established Sika deer population. This property offers a unique opportunity to enjoy legitimate hunting and outdoor recreation from a private home site while being fully immersed within one of Maryland’s most iconic conservation landscapes. Whether used as a full-time residence, weekend retreat, or generational sporting property, Maple Dam Road delivers an exceptional blend of access, privacy, and outdoor heritage that is increasingly difficult to find on the Eastern Shore. A BAT System upgrade plan has been developed to bring BAT/BIP System up to standards. Contact for additional information.

3819 Maple Dam Rd, Cambridge

Listing courtesy of The Land Group. Contact: (410) 934-3478
$489,000
3 Beds ⋅ 2 Baths
9 West End Avenue - a perfect blend of sophistication and tranquility. #9 is proudly sited on the corner of West End Avenue and Hambrooks Blvd...just 5 houses from the banks of the mighty Choptank River! Now is the perfect time to host an upstairs porch party with views of the beautiful river. # 9 has been quietly owned by a professional couple from DC for almost 20 years. You can see the subtle city influence in various details of every room, but, more importantly, you can glimpse the wife's artistic attention to minute details throughout this charming haven. Charles Goebel, a highly-respected Easton architect designed the renovations and additions. The work was flawlessly executed by esteemed Cambridge builder Thom Huntington. The renovations included a new Living Room, a glamorous first-floor bathroom, and generously-sized porches on the first floor, covered by a gull-winged roof. The outstanding spacious kitchen features a multitude of light sources, a top-of-the-line propane range with hood, a built-in microwave drawer, and beautiful Carrara marble countertops and backsplash. A pass-through bar area to the dining room provides a great casual seating arrangement in addition to the formal dining room. The upstairs second floor offers 3 bedrooms and a full bath but the most captivating aspect of the 2nd floor is the beautiful balcony off the central hall. The balcony has views of the river and the beautifully landscaped garden. In total, there are 4 outdoor porches and balconies. The back garden is an amazing oasis of specimen plantings and magnificent trees. The well-placed potting shed makes gardening a delight. The front porch's trompe l'oeil floor and sky ceiling were designed and painted by Mike Rosato, a locally acclaimed artist whose work can be found throughout the city and in numerous museums throughout the country. #9 West End's location is ideal for strolling to the Farmers Market or the Cambridge Yacht Club and is just a short walk to all of the downtown restaurants, galleries, and shops. The renaissance in Cambridge is alive and flourishing. Please call Mary for additional details and a tour today!

9 W End Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$59,950
Price Improvement — Beautiful Homesite Near the Water in Ferry Farms Take advantage of a rare opportunity to own this 2.20± acre homesite in the sought-after Ferry Farms community. Located just a short walk from the water and the community pier, this property offers a peaceful, private setting bordered by wooded, community-owned open space. The natural surroundings create a tranquil retreat with a scenic, tree-lined backdrop perfect for relaxing and enjoying the outdoors. Whether you’re planning a full-time residence or a weekend escape, this property offers the ideal setting to build your custom home near the water while still enjoying privacy and the beauty of nature. Buyer Notice: Buyers are encouraged to contact the Maryland Department of the Environment (MDE) and Dorchester County Planning & Zoning to confirm all building requirements, including wetlands or Critical Area considerations, possible restrictions, and connection requirements for the community B.I.P. system. Plat, covenants, and restrictions are available in the document section.

814 Cody Dr Unit #LOT 17, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$125,000
Large lot in northern Dorchester County, well located with easy access to Cambridge and Easton for work and play. Delaware not far for tax free purchases. Wooded with mature pine and hardwood in a rural area of open farmland offering privacy. Lot size is 6.51 acres, of which 4.48 is in a forest conservation area, leaving more than ample room of 2.03 acres for your new home and other improvements. (see plat in Documents). Home site is partially cleared. There are deed restrictions for value protection which are not too burdensome. This is a finished lot ready for home construction, Contact Dorchester County Dept of Planning and zoning for permitting

Gravel Branch Rd, Hurlock

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