easternshoremdfineproperties.com Search Results

$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

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.

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

$685,000

Waterfront Living at Its Finest! Situated on 1.2 acres along the shores of beautiful Todds Bay with sweeping views of the Choptank River, this exceptional waterfront property offers the perfect blend of relaxation and recreation. Enjoy stunning water vistas from the comfort of your sunroom, unwind by the cozy fireplace, or step outside to your private dock complete with a boat lift. Spend your days boating, kayaking, paddle boarding, fishing, or crabbing right from your own pier. The property features both a garage and carport, providing ample space for vehicles, boats, and storage. Whether you're seeking a full-time residence or a weekend retreat, this home embraces the very best of Eastern Shore waterfront living. Conveniently located just minutes from charming historic downtown, you'll enjoy easy access to unique shops, local eateries, waterfront dining, and community events. Experience the spectacular sun rise, endless water activities, and a lifestyle centered around the beauty of the Chesapeake Bay region.

4 Beds ⋅ 3 Baths

Waterfront Living at Its Finest! Situated on 1.2 acres along the shores of beautiful Todds Bay with sweeping views of the Choptank River, this exceptional waterfront property offers the perfect blend of relaxation and recreation. Enjoy stunning water vistas from the comfort of your sunroom, unwind by the cozy fireplace, or step outside to your private dock complete with a boat lift. Spend your days boating, kayaking, paddle boarding, fishing, or crabbing right from your own pier. The property features both a garage and carport, providing ample space for vehicles, boats, and storage. Whether you're seeking a full-time residence or a weekend retreat, this home embraces the very best of Eastern Shore waterfront living. Conveniently located just minutes from charming historic downtown, you'll enjoy easy access to unique shops, local eateries, waterfront dining, and community events. Experience the spectacular sun rise, endless water activities, and a lifestyle centered around the beauty of the Chesapeake Bay region.

1022 River Point Rd, Cambridge

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

$849,900

Trade Traffic for Tides — Your Waterfront Island Escape Awaits! From the moment you cross the bridge onto Hooper's Island, something changes. A sense of peace settles in. Life slows down. The water sets the schedule, neighbors wave as they pass, and the pace becomes simpler, sweeter, and slower—in the very best way. This beautifully remodeled 3-bedroom, 2-full-bath waterfront home is being offered fully furnished and is already an established, highly successful 5-star Airbnb, renting for $430 per night. Whether you're looking for a personal island retreat, an investment property, or the best of both worlds, this home is ready to enjoy from day one. The entire home has been remodeled from the ground up, so nothing in the home is older than 5 years old- appliances, roof, well, mechanicals -you name it!! Imagine looking out your window and seeing crab boats, dolphins playing in the bay, and cruise ships and container vessels making their way across the horizon. A rear wall of floor-to-ceiling glass doors provides panoramic bay views, bringing the water into nearly every room. Cooking becomes relaxing because the views are amazing, even from the kitchen! Wake in the primary suite, open the blinds with a remote control, and take in the water views from the comfort of your bed. Freshly painted and featuring brand-new flooring throughout, the home combines comfortable coastal living with thoughtful modern updates. The crawl space had spray foam insulation, vapor barrier, and a new sump pump installed in 2026. The home is ADA accessible with a ramp to enter from the side, walk-in showers, wrap around Trex decking, and even paved sidewalks with railings leading the whole way to the dock. Smart technology integrated into so many aspects of the property! Access an app to control the thermostat, garage door, RING cameras, and even view the contents of your fridge so you can remember what you need to get at the grocery store! And then there's the waterfront. A private dock, built just two years ago, is ready for your next adventure and includes a 10,000-pound boat lift. Spend your days kayaking, swimming, boating, jet skiing, fishing, or crabbing—or simply sit by the water and watch island life unfold. Search the shoreline for sea glass and seashells, launch the kayak, or cast a line and see what the day brings. On this island, you won't need your car. Leave it parked and explore by foot, bike, or golf cart. Hooper's Island has a general store stocked with everyday essentials, from fishing tackle to ice cream, and Old Salty's, the island's only restaurant, serves wonderful fresh seafood alongside a laid-back tiki bar. Fun fact about Hooper's Island: Before it started as a culinary legend, it all started on this island in 1914 when Augustus E. Phillips opened the A.E. Phillips & Son packing plant. In 1956, faced with a surplus of crabs, Augustus' son and his wife opened a small 'shack' in Ocean City, MD... and we all know how that exploded with popularity! The original processing plant is still part of the company, and when operational, continues to process blue crabs and soft-shell crabs for regional locations.

3 Beds ⋅ 2 Baths

Trade Traffic for Tides — Your Waterfront Island Escape Awaits! From the moment you cross the bridge onto Hooper's Island, something changes. A sense of peace settles in. Life slows down. The water sets the schedule, neighbors wave as they pass, and the pace becomes simpler, sweeter, and slower—in the very best way. This beautifully remodeled 3-bedroom, 2-full-bath waterfront home is being offered fully furnished and is already an established, highly successful 5-star Airbnb, renting for $430 per night. Whether you're looking for a personal island retreat, an investment property, or the best of both worlds, this home is ready to enjoy from day one. The entire home has been remodeled from the ground up, so nothing in the home is older than 5 years old- appliances, roof, well, mechanicals -you name it!! Imagine looking out your window and seeing crab boats, dolphins playing in the bay, and cruise ships and container vessels making their way across the horizon. A rear wall of floor-to-ceiling glass doors provides panoramic bay views, bringing the water into nearly every room. Cooking becomes relaxing because the views are amazing, even from the kitchen! Wake in the primary suite, open the blinds with a remote control, and take in the water views from the comfort of your bed. Freshly painted and featuring brand-new flooring throughout, the home combines comfortable coastal living with thoughtful modern updates. The crawl space had spray foam insulation, vapor barrier, and a new sump pump installed in 2026. The home is ADA accessible with a ramp to enter from the side, walk-in showers, wrap around Trex decking, and even paved sidewalks with railings leading the whole way to the dock. Smart technology integrated into so many aspects of the property! Access an app to control the thermostat, garage door, RING cameras, and even view the contents of your fridge so you can remember what you need to get at the grocery store! And then there's the waterfront. A private dock, built just two years ago, is ready for your next adventure and includes a 10,000-pound boat lift. Spend your days kayaking, swimming, boating, jet skiing, fishing, or crabbing—or simply sit by the water and watch island life unfold. Search the shoreline for sea glass and seashells, launch the kayak, or cast a line and see what the day brings. On this island, you won't need your car. Leave it parked and explore by foot, bike, or golf cart. Hooper's Island has a general store stocked with everyday essentials, from fishing tackle to ice cream, and Old Salty's, the island's only restaurant, serves wonderful fresh seafood alongside a laid-back tiki bar. Fun fact about Hooper's Island: Before it started as a culinary legend, it all started on this island in 1914 when Augustus E. Phillips opened the A.E. Phillips & Son packing plant. In 1956, faced with a surplus of crabs, Augustus' son and his wife opened a small 'shack' in Ocean City, MD... and we all know how that exploded with popularity! The original processing plant is still part of the company, and when operational, continues to process blue crabs and soft-shell crabs for regional locations.

1210 Horse Point Rd, Fishing Creek

Listing courtesy of Contigo Real Estate. Contact: 7172694566

$649,000

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.

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

$424,900

One of a kind 31+ acre farmette with established trails, open fields, ponds and Farm Creek water frontage, offering excellent Sika deer, goose and duck hunting and endless opportunities to enjoy the outdoors. The property includes a well-maintained 3 bedroom, 2 3/4 bath home with a conditioned crawl space, 3 stall barn, fenced pastures, pole barn and shop/shed. The perfect blend of recreation, hobby farming and peaceful country living for the hunter and nature enthusiast alike.

3 Beds ⋅ 3 Baths

One of a kind 31+ acre farmette with established trails, open fields, ponds and Farm Creek water frontage, offering excellent Sika deer, goose and duck hunting and endless opportunities to enjoy the outdoors. The property includes a well-maintained 3 bedroom, 2 3/4 bath home with a conditioned crawl space, 3 stall barn, fenced pastures, pole barn and shop/shed. The perfect blend of recreation, hobby farming and peaceful country living for the hunter and nature enthusiast alike.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$799,900

Experience the natural beauty and tranquility of Maryland's Eastern Shore from this exceptional waterfront retreat in Dorchester County. Tucked away at the end of a private street on Brooks Creek, this remarkable property boasts over 180 degrees of breathtaking water views from its spectacular lot. Designed for boating enthusiasts, the waterfront features approximately 120 feet of pier with multiple boat lifts, a bulk headed shoreline, a private boat ramp, a small sandy beach, and expansive lawn surrounded by mature landscaping. This charming 4-bedroom, 3-bath home has been thoughtfully designed to capture panoramic water views from virtually every room. The updated kitchen features granite countertops, stainless steel appliances, and ample workspace, while hardwood flooring flows throughout the main living areas. The open floor plan seamlessly connects the spacious dining area and living room, creating an inviting setting for everyday living and entertaining. Three generously sized bedrooms are located on the main level. The impressive family room is the heart of the home, showcasing a gas fireplace, built-in bar, and walls of windows that frame the ever-changing waterfront scenery. Upstairs, the private primary suite is a true sanctuary, featuring soaring cathedral ceilings and dramatic floor-to-ceiling windows that provide sweeping panoramic water views from both the sleeping and sitting areas. A second gas fireplace creates a cozy atmosphere, while the luxurious en-suite bath offers a garden tub, walk-in shower, and spacious walk-in closet. Outdoor living is equally exceptional. Relax on the expansive screened porch while enjoying spectacular sunsets and the abundant wildlife and waterfowl that call Brooks Creek home. An oversized concrete patio provides additional space for entertaining, and two storage sheds—including one equipped with two refrigerators—offer excellent convenience for boating, fishing, and gatherings. Dual driveways provide ample parking for multiple vehicles, boats, and trailers. From your private pier, enjoy easy access by boat to Tilghman Island, St. Michaels, and many of the Mid-Shore's most charming waterfront towns, where you'll find renowned restaurants, marinas, boutique shopping, and endless opportunities to experience the best of Eastern Shore living. Whether you're seeking a full-time residence, weekend escape, or the ultimate waterfront lifestyle, this rare Brooks Creek property offers an extraordinary combination of privacy, recreation, and unforgettable views.

4 Beds ⋅ 3 Baths

Experience the natural beauty and tranquility of Maryland's Eastern Shore from this exceptional waterfront retreat in Dorchester County. Tucked away at the end of a private street on Brooks Creek, this remarkable property boasts over 180 degrees of breathtaking water views from its spectacular lot. Designed for boating enthusiasts, the waterfront features approximately 120 feet of pier with multiple boat lifts, a bulk headed shoreline, a private boat ramp, a small sandy beach, and expansive lawn surrounded by mature landscaping. This charming 4-bedroom, 3-bath home has been thoughtfully designed to capture panoramic water views from virtually every room. The updated kitchen features granite countertops, stainless steel appliances, and ample workspace, while hardwood flooring flows throughout the main living areas. The open floor plan seamlessly connects the spacious dining area and living room, creating an inviting setting for everyday living and entertaining. Three generously sized bedrooms are located on the main level. The impressive family room is the heart of the home, showcasing a gas fireplace, built-in bar, and walls of windows that frame the ever-changing waterfront scenery. Upstairs, the private primary suite is a true sanctuary, featuring soaring cathedral ceilings and dramatic floor-to-ceiling windows that provide sweeping panoramic water views from both the sleeping and sitting areas. A second gas fireplace creates a cozy atmosphere, while the luxurious en-suite bath offers a garden tub, walk-in shower, and spacious walk-in closet. Outdoor living is equally exceptional. Relax on the expansive screened porch while enjoying spectacular sunsets and the abundant wildlife and waterfowl that call Brooks Creek home. An oversized concrete patio provides additional space for entertaining, and two storage sheds—including one equipped with two refrigerators—offer excellent convenience for boating, fishing, and gatherings. Dual driveways provide ample parking for multiple vehicles, boats, and trailers. From your private pier, enjoy easy access by boat to Tilghman Island, St. Michaels, and many of the Mid-Shore's most charming waterfront towns, where you'll find renowned restaurants, marinas, boutique shopping, and endless opportunities to experience the best of Eastern Shore living. Whether you're seeking a full-time residence, weekend escape, or the ultimate waterfront lifestyle, this rare Brooks Creek property offers an extraordinary combination of privacy, recreation, and unforgettable views.

803 Seabreeze Rd, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 520-2707

$624,000

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.

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

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.

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

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.

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

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.

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:

$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

$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

$1,399,000

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

6 Beds ⋅ 5 Baths

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

5332 Ragged Point Rd, Cambridge

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

$1,195,000

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

4 Beds ⋅ 4 Baths

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

1661 Town Point Rd, Cambridge

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

$998,500

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

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

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.

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

$650,000

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.

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:

$378,000

102.4 Acres of prime waterfowl hunting. Property is 2 parcels. Parcel 4 is 35 Acres and Parcel 5 is 67.4 Acres. Parcel 5 was subdivided in January of 2026 and was originally 131 Acres.

Griffith Neck Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$675,000

Do you dream of a serene waterfront escape with room for horses, privacy, and the opportunity to create something truly special? Recently PERC APPROVED for a 5-bedroom home, this 10-acre horse farm on Hudson Creek offers exciting new possibilities to renovate the existing residence or build the waterfront home you’ve envisioned. The property is already well equipped for equestrian use with two fenced pastures, a barn, run-in shed, storage shed, and fresh water systems for the horses. Surrounded by wide-open space and limited future development, the setting offers exceptional privacy and peaceful, protected views. Water lovers will appreciate the 100-foot T-shaped pier with over 4 feet of mean low water on protected Hudson Creek, providing easy access to the Chesapeake Bay and some of the area’s best fishing and crabbing. A charming old crab shack near the shoreline offers additional potential with some repairs. An oversized detached brick 4-car garage provides plenty of room for a workshop, hobby equipment, boats, or collectible vehicles. The existing all-brick home is being sold AS IS and features three bedrooms, two-and-a-half baths, a brick fireplace, and attached 2-car garage. With 10 waterfront acres, established equestrian amenities, deep-water access, and the recent 5-bedroom PERC approval, this property presents a rare opportunity to bring your vision to life on Maryland’s Eastern Shore.

5816 Indian Quarter Rd, Cambridge

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

$850,000

Stunning Custom-Built Coastal Home with Private Beach! This one-of-a-kind coastal home represents over three years of meticulous planning and construction, designed for maximum durability, energy efficiency, and minimal maintenance. No detail has been overlooked in this custom build, which showcases a thoughtful blend of modern features and antique charm. Structural Features: Oversized footers with rebar for a solid foundation Extra-deep 12-inch stone driveway with Typar fabric for durability New culvert pipe at the entrance and concrete-filled block walls, tying everything together for added strength and protection. Flood gates at grade level to safeguard against water entry Block-constructed interior stair tower to ensure no water enters the living space Premium framing using Number 1 Select Southern Yellow Pine, with 9-foot walls and 2x12 floor joists for a rock-solid structure. Truss roof system with hurricane clips, blanket insulation, and metal roofing to prevent sweating Garage & Exterior: 12-inch stone base and 6-inch, 5000 PSI concrete garage floor Fully insulated, stainless steel garage doors Tyvek wrap on the exterior, with reflective 3/8” fan-fold insulation for added energy efficiency PVC trim with a hidden plug system for a clean look Cedar panel siding rated for 130 mph winds Low-maintenance, commercial-grade fiberglass decking with a structural steel frame, hot-dip galvanized for durability Aluminum handrails, powder-coated white for a sleek, coastal design Interior Features & Custom Details: Unique antique accents, including a bronze ship bell mounted on an antique column in the stairwell Spanish-American War fireback backsplash and a historic cast-iron fireplace from Washington, DC Early Bombay-style dresser vanity in the master bathroom with a matching mirror, stained to complement the home’s coastal color palette Handrail leading to the basement crafted from a traditional oar to enhance the coastal theme All wood used is top-tier, including number one clear pressure-treated decking and stainless steel screws for long-lasting performance Energy Efficiency & Sustainability: Air-sealed prior to insulation, with spray foam insulation in walls, floors, band boards, and attic (R-30 in floors, R-60 in the attic) HVAC and attic areas also receive spray foam for maximum efficiency Baffles installed at eaves for optimal airflow, reducing energy costs Electric bills averaging just $100 per month Fire sprinkler system with a discreetly located tank and pump for safety Gourmet Kitchen & Bathrooms: Custom oak kitchen cabinets, painted to match the tongue-and-groove ceiling High-end, 36-inch stainless steel gas stove and energy-efficient appliances Premium Fantasy Brown marble countertops (two grades above granite), sourced from a single slab Arabesque tile backsplash to complete the kitchen design All bathrooms feature white subway tile, with a master bath receiving marble accents and a guest bathroom enhanced with green sea glass accents Both bathrooms include rain showerheads and hand showers for easy cleaning Interior Finishes: Nickel gap walls throughout the kitchen, living room, and hallway, and tongue-and-groove ceilings throughout Solid wood doors with frosted glass inserts and crystal knobs for an elegant touch Stained oak stair treads and handrails, complemented by luxury glue-down commercial plank flooring Thoughtful design focused on safety, efficiency, and low maintenance This home was built with care, incorporating over 40 years of experience and a passion for creating a space that is both functional and beautiful. Perfectly designed to withstand the elements and deliver comfort and style, this is a rare opportunity to own a property that blends the best of modern living with historic charm. Contact us today to schedule your private tour and see firsthand the unmatched craftsmanship and attention to detail that went into this extraordinary home! Be sure to visit the drone and virtual tours of the home

2 Beds ⋅ 2 Baths

Stunning Custom-Built Coastal Home with Private Beach! This one-of-a-kind coastal home represents over three years of meticulous planning and construction, designed for maximum durability, energy efficiency, and minimal maintenance. No detail has been overlooked in this custom build, which showcases a thoughtful blend of modern features and antique charm. Structural Features: Oversized footers with rebar for a solid foundation Extra-deep 12-inch stone driveway with Typar fabric for durability New culvert pipe at the entrance and concrete-filled block walls, tying everything together for added strength and protection. Flood gates at grade level to safeguard against water entry Block-constructed interior stair tower to ensure no water enters the living space Premium framing using Number 1 Select Southern Yellow Pine, with 9-foot walls and 2x12 floor joists for a rock-solid structure. Truss roof system with hurricane clips, blanket insulation, and metal roofing to prevent sweating Garage & Exterior: 12-inch stone base and 6-inch, 5000 PSI concrete garage floor Fully insulated, stainless steel garage doors Tyvek wrap on the exterior, with reflective 3/8” fan-fold insulation for added energy efficiency PVC trim with a hidden plug system for a clean look Cedar panel siding rated for 130 mph winds Low-maintenance, commercial-grade fiberglass decking with a structural steel frame, hot-dip galvanized for durability Aluminum handrails, powder-coated white for a sleek, coastal design Interior Features & Custom Details: Unique antique accents, including a bronze ship bell mounted on an antique column in the stairwell Spanish-American War fireback backsplash and a historic cast-iron fireplace from Washington, DC Early Bombay-style dresser vanity in the master bathroom with a matching mirror, stained to complement the home’s coastal color palette Handrail leading to the basement crafted from a traditional oar to enhance the coastal theme All wood used is top-tier, including number one clear pressure-treated decking and stainless steel screws for long-lasting performance Energy Efficiency & Sustainability: Air-sealed prior to insulation, with spray foam insulation in walls, floors, band boards, and attic (R-30 in floors, R-60 in the attic) HVAC and attic areas also receive spray foam for maximum efficiency Baffles installed at eaves for optimal airflow, reducing energy costs Electric bills averaging just $100 per month Fire sprinkler system with a discreetly located tank and pump for safety Gourmet Kitchen & Bathrooms: Custom oak kitchen cabinets, painted to match the tongue-and-groove ceiling High-end, 36-inch stainless steel gas stove and energy-efficient appliances Premium Fantasy Brown marble countertops (two grades above granite), sourced from a single slab Arabesque tile backsplash to complete the kitchen design All bathrooms feature white subway tile, with a master bath receiving marble accents and a guest bathroom enhanced with green sea glass accents Both bathrooms include rain showerheads and hand showers for easy cleaning Interior Finishes: Nickel gap walls throughout the kitchen, living room, and hallway, and tongue-and-groove ceilings throughout Solid wood doors with frosted glass inserts and crystal knobs for an elegant touch Stained oak stair treads and handrails, complemented by luxury glue-down commercial plank flooring Thoughtful design focused on safety, efficiency, and low maintenance This home was built with care, incorporating over 40 years of experience and a passion for creating a space that is both functional and beautiful. Perfectly designed to withstand the elements and deliver comfort and style, this is a rare opportunity to own a property that blends the best of modern living with historic charm. Contact us today to schedule your private tour and see firsthand the unmatched craftsmanship and attention to detail that went into this extraordinary home! Be sure to visit the drone and virtual tours of the home

1826 Hoopersville, Fishing Creek

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011