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Welcome to your private waterfront retreat, where sweeping views of the Little Annemessex River can be enjoyed from nearly every room. Nestled on approximately four and half acres, this spacious four bedroom, three and-a-half bath home offers a rare combination of privacy, comfort, and true Eastern Shore waterfront living. Step inside through the impressive foyer, with a conveniently located powder room nearby, and continue into the main living area featuring soaring vaulted ceilings and beautiful crown molding. Just beyond the living room, a light-filled sunroom showcases expansive windows overlooking the river is an ideal place to unwind while taking in the breathtaking colors of the sunrise and sunset over the water. The main living space flows effortlessly into the gourmet kitchen, complete with custom cabinetry and plenty of room for cooking and entertaining. The first-floor primary suite provides a peaceful retreat with a spacious en-suite bath featuring a walk-in shower, large jetted tub, and double vanities. A separate wing of the home offers two additional bedrooms and a full hallway bath, providing privacy and flexibility for family or guests. Above the oversized two-car garage is a private guest or in-law suite featuring a generously sized bedroom, full bath, and large walk-in closet. The home also offers abundant attic storage with the potential for additional finished space, if desired. Outside, the expansive rear deck creates the perfect setting for family gatherings, outdoor entertaining, or quiet evenings surrounded by nature and spectacular waterfront views. A dock permit has already been approved by the Maryland Department of the Environment, giving the future owner the opportunity to create direct boating access just steps from home. For added peace of mind, the home has already been pre-inspected, allowing buyers to move forward with greater confidence. Whether you are searching for a year-round residence or a peaceful waterfront escape, this exceptional property offers the space, scenery, and lifestyle to enjoy everything the Chesapeake Bay region has to offer. Additional parcel at front of property with separate tax id will also be included with the sale for a final total of 5.356 acres.

4 Beds ⋅ 4 Baths

Welcome to your private waterfront retreat, where sweeping views of the Little Annemessex River can be enjoyed from nearly every room. Nestled on approximately four and half acres, this spacious four bedroom, three and-a-half bath home offers a rare combination of privacy, comfort, and true Eastern Shore waterfront living. Step inside through the impressive foyer, with a conveniently located powder room nearby, and continue into the main living area featuring soaring vaulted ceilings and beautiful crown molding. Just beyond the living room, a light-filled sunroom showcases expansive windows overlooking the river is an ideal place to unwind while taking in the breathtaking colors of the sunrise and sunset over the water. The main living space flows effortlessly into the gourmet kitchen, complete with custom cabinetry and plenty of room for cooking and entertaining. The first-floor primary suite provides a peaceful retreat with a spacious en-suite bath featuring a walk-in shower, large jetted tub, and double vanities. A separate wing of the home offers two additional bedrooms and a full hallway bath, providing privacy and flexibility for family or guests. Above the oversized two-car garage is a private guest or in-law suite featuring a generously sized bedroom, full bath, and large walk-in closet. The home also offers abundant attic storage with the potential for additional finished space, if desired. Outside, the expansive rear deck creates the perfect setting for family gatherings, outdoor entertaining, or quiet evenings surrounded by nature and spectacular waterfront views. A dock permit has already been approved by the Maryland Department of the Environment, giving the future owner the opportunity to create direct boating access just steps from home. For added peace of mind, the home has already been pre-inspected, allowing buyers to move forward with greater confidence. Whether you are searching for a year-round residence or a peaceful waterfront escape, this exceptional property offers the space, scenery, and lifestyle to enjoy everything the Chesapeake Bay region has to offer. Additional parcel at front of property with separate tax id will also be included with the sale for a final total of 5.356 acres.

26128 Byrd Rd, Crisfield

Listing courtesy of Keller Williams Realty. Contact:

$499,000

Rare waterfront penthouse living at Captains Quarters in Crisfield, Maryland. This 4th-floor, 3-bedroom, 3-bath condominium offers approximately 1,753 square feet of one-level living, elevator access, and a premier marina-front setting. The larger floor plan and three full baths provide comfort and flexibility for full-time living, a second home, or hosting family and guests, creating value rarely found in smaller waterfront condos. Expansive outdoor living areas include multiple balconies, wraparound deck space, and a rooftop patio with panoramic views of Tangier Sound, Somers Cove Marina, Daugherty Creek, the harbor, and the surrounding waterfront. From sunrise over Somers Cove to sunset over Tangier Sound, this property delivers more than a view — it offers a daily waterfront experience. Inside, the open living and dining area features cathedral ceilings, Brazilian cherry hardwood flooring, crown molding, a gas fireplace, and direct balcony access. The distinctive two-story turret adds architectural character and natural light, making the dining area a true focal point. The kitchen includes granite countertops, breakfast bar seating, recessed lighting, double sink, wall oven, convection oven, oversized refrigerator, dishwasher, disposal, microwave, stove, and trash compactor. The primary suite offers balcony access, water views, cathedral ceiling, hardwood flooring, attached bath, and large dual closets. Additional bedrooms are generously sized, with one offering attached bath access and balcony access, giving guests privacy and comfort. Interior features also include a slate foyer, built-ins, upgraded countertops, ceiling fans, recessed lighting, window treatments, sound system, and in-unit washer and dryer. Community amenities include common grounds, elevator, extra storage, pier/dock access, reserved parking, and assigned parking. The condo fee includes common area maintenance, exterior building maintenance, insurance, lawn maintenance, sewer, trash, and water. A new roof was installed in October 2025, and condo assessment fees have been paid. Located near Somers Cove Marina, public boat launch access, fishing, kayaking, local dining, ferry activity, Janes Island State Park, the Tawes Museum, and Crisfield’s waterfront district, Unit 402 offers space, views, lifestyle, and long-term coastal appeal. This is not simply another condo — it is a rare marina-front penthouse opportunity on Maryland’s Lower Eastern Shore. Schedule your private tour and experience the view for yourself.

3 Beds ⋅ 3 Baths

Rare waterfront penthouse living at Captains Quarters in Crisfield, Maryland. This 4th-floor, 3-bedroom, 3-bath condominium offers approximately 1,753 square feet of one-level living, elevator access, and a premier marina-front setting. The larger floor plan and three full baths provide comfort and flexibility for full-time living, a second home, or hosting family and guests, creating value rarely found in smaller waterfront condos. Expansive outdoor living areas include multiple balconies, wraparound deck space, and a rooftop patio with panoramic views of Tangier Sound, Somers Cove Marina, Daugherty Creek, the harbor, and the surrounding waterfront. From sunrise over Somers Cove to sunset over Tangier Sound, this property delivers more than a view — it offers a daily waterfront experience. Inside, the open living and dining area features cathedral ceilings, Brazilian cherry hardwood flooring, crown molding, a gas fireplace, and direct balcony access. The distinctive two-story turret adds architectural character and natural light, making the dining area a true focal point. The kitchen includes granite countertops, breakfast bar seating, recessed lighting, double sink, wall oven, convection oven, oversized refrigerator, dishwasher, disposal, microwave, stove, and trash compactor. The primary suite offers balcony access, water views, cathedral ceiling, hardwood flooring, attached bath, and large dual closets. Additional bedrooms are generously sized, with one offering attached bath access and balcony access, giving guests privacy and comfort. Interior features also include a slate foyer, built-ins, upgraded countertops, ceiling fans, recessed lighting, window treatments, sound system, and in-unit washer and dryer. Community amenities include common grounds, elevator, extra storage, pier/dock access, reserved parking, and assigned parking. The condo fee includes common area maintenance, exterior building maintenance, insurance, lawn maintenance, sewer, trash, and water. A new roof was installed in October 2025, and condo assessment fees have been paid. Located near Somers Cove Marina, public boat launch access, fishing, kayaking, local dining, ferry activity, Janes Island State Park, the Tawes Museum, and Crisfield’s waterfront district, Unit 402 offers space, views, lifestyle, and long-term coastal appeal. This is not simply another condo — it is a rare marina-front penthouse opportunity on Maryland’s Lower Eastern Shore. Schedule your private tour and experience the view for yourself.

1 Dock St Unit 402, Crisfield

Listing courtesy of ERA Martin Associates. Contact:

$199,000

Welcome to 5 Potomac Street, a charming home nestled in a quiet neighborhood and ready for its next owner. Step inside to a spacious living room featuring beautiful brick fireplace with a pellet stove insert, creating a warm and inviting focal point. Just off the living room is an enclosed porch the perfect spot to enjoy your morning coffee or unwind at the end of the day. The living room flows into a generously sized dining area and adjoining kitchen. Located at the rear of the home is a convenient utility room with washer and dryer hookups, along with a new electric water heater. The first floor offers two bedrooms with an adjoining full bathroom. Upstairs, you’ll find a spacious third bedroom that could also serve as a flex space, home office, or additional living area, as well as a separate full bathroom featuring a new shower insert. New mini-split HVAC systems provide efficient heating and cooling throughout the home. A new refrigerator will also be installed prior to closing. Turnkey and ready to welcome its new owners, 5 Potomac Street offers comfortable living, flexible space, and plenty of charm!

3 Beds ⋅ 2 Baths

Welcome to 5 Potomac Street, a charming home nestled in a quiet neighborhood and ready for its next owner. Step inside to a spacious living room featuring beautiful brick fireplace with a pellet stove insert, creating a warm and inviting focal point. Just off the living room is an enclosed porch the perfect spot to enjoy your morning coffee or unwind at the end of the day. The living room flows into a generously sized dining area and adjoining kitchen. Located at the rear of the home is a convenient utility room with washer and dryer hookups, along with a new electric water heater. The first floor offers two bedrooms with an adjoining full bathroom. Upstairs, you’ll find a spacious third bedroom that could also serve as a flex space, home office, or additional living area, as well as a separate full bathroom featuring a new shower insert. New mini-split HVAC systems provide efficient heating and cooling throughout the home. A new refrigerator will also be installed prior to closing. Turnkey and ready to welcome its new owners, 5 Potomac Street offers comfortable living, flexible space, and plenty of charm!

5 Potomac St, Crisfield

Listing courtesy of Keller Williams Realty. Contact:

$145,000

Back on market to no fault of seller! Nestled in the charming of Crisfield, this delightful bungalow offers a perfect blend of comfort and functionality. Built in 1940, this home has been lovingly maintained and features a traditional floor plan that invites warmth and togetherness. With 1,312 square feet of finished living space, this residence boasts three cozy bedrooms and a full bathroom, making it an ideal retreat for anyone seeking a peaceful haven. Step inside to discover a welcoming family room that seamlessly connects to the dining room , creating an inviting atmosphere for gatherings and everyday living. The efficiency kitchen is equipped with essential appliances, including a built-in microwave, electric oven/range, refrigerator, and a convenient washer and dryer. The charming brick fireplace serves as a focal point, perfect for cozy evenings spent with loved ones. The interior features carpeting and ceiling fans , ensuring comfort in every season. An entry-level bedroom adds to the home's versatility, making it suitable for guests or as a home office. Outside, the property sits on a generous 0.48-acre lot, offering ample space for outdoor activities and gardening with fenced in yard. The cleared yard is beautifully landscaped, providing a serene backdrop for relaxation or entertaining. The extensive hardscape and gutter system enhance the exterior, ensuring low maintenance and practicality. Parking is a breeze with an asphalt driveway that accommodates up to two vehicles. Crisfield is not just a place to live; it's a community that thrives on connection and convenience. This charming bungalow is more than just a house; it's a place where memories are made and cherished. New roof was put on this year! There is a $1500 carpet allowance for kitchen & hall!!

3 Beds ⋅ 1 Baths

Back on market to no fault of seller! Nestled in the charming of Crisfield, this delightful bungalow offers a perfect blend of comfort and functionality. Built in 1940, this home has been lovingly maintained and features a traditional floor plan that invites warmth and togetherness. With 1,312 square feet of finished living space, this residence boasts three cozy bedrooms and a full bathroom, making it an ideal retreat for anyone seeking a peaceful haven. Step inside to discover a welcoming family room that seamlessly connects to the dining room , creating an inviting atmosphere for gatherings and everyday living. The efficiency kitchen is equipped with essential appliances, including a built-in microwave, electric oven/range, refrigerator, and a convenient washer and dryer. The charming brick fireplace serves as a focal point, perfect for cozy evenings spent with loved ones. The interior features carpeting and ceiling fans , ensuring comfort in every season. An entry-level bedroom adds to the home's versatility, making it suitable for guests or as a home office. Outside, the property sits on a generous 0.48-acre lot, offering ample space for outdoor activities and gardening with fenced in yard. The cleared yard is beautifully landscaped, providing a serene backdrop for relaxation or entertaining. The extensive hardscape and gutter system enhance the exterior, ensuring low maintenance and practicality. Parking is a breeze with an asphalt driveway that accommodates up to two vehicles. Crisfield is not just a place to live; it's a community that thrives on connection and convenience. This charming bungalow is more than just a house; it's a place where memories are made and cherished. New roof was put on this year! There is a $1500 carpet allowance for kitchen & hall!!

31 Wynfall, Crisfield

Listing courtesy of LAIRD & ASSOCIATES. Contact:

$95,000

Welcome to 108 W Chesapeake Avenue in the heart of Crisfield, Maryland, known as the "Crab Capital of the World" and gateway to the beautiful Chesapeake Bay. This charming 3-bedroom, 1.5-bath home offers a blend of historic character and recent updates, making it a great opportunity for homeowners, investors, or those looking for a coastal retreat. Step inside and be greeted by the beautiful original hardwood floors, a spacious foyer, and a stunning solid wood staircase that showcases the home's timeless craftsmanship. The main level features a large living room that flows into an expansive family room, providing plenty of space for gathering and entertaining. Toward the rear of the home, you'll find a generously sized kitchen, dining room, and convenient utility room. Upstairs offers three comfortable bedrooms and a full bathroom. Outside, enjoy relaxing on the screened wraparound front porch, perfect for taking in the coastal breeze without the bugs. The manageable yard includes a fenced area ideal for pets, gardening, or outdoor enjoyment. Located just minutes from Crisfield's waterfront, marina, restaurants, festivals, and ferry service to Smith Island, this home provides easy access to the Eastern Shore lifestyle. Whether you're looking for a primary residence, vacation getaway, or investment property, this home is full of potential. Property is being sold As-Is. Schedule your private showing today!

3 Beds ⋅ 2 Baths

Welcome to 108 W Chesapeake Avenue in the heart of Crisfield, Maryland, known as the "Crab Capital of the World" and gateway to the beautiful Chesapeake Bay. This charming 3-bedroom, 1.5-bath home offers a blend of historic character and recent updates, making it a great opportunity for homeowners, investors, or those looking for a coastal retreat. Step inside and be greeted by the beautiful original hardwood floors, a spacious foyer, and a stunning solid wood staircase that showcases the home's timeless craftsmanship. The main level features a large living room that flows into an expansive family room, providing plenty of space for gathering and entertaining. Toward the rear of the home, you'll find a generously sized kitchen, dining room, and convenient utility room. Upstairs offers three comfortable bedrooms and a full bathroom. Outside, enjoy relaxing on the screened wraparound front porch, perfect for taking in the coastal breeze without the bugs. The manageable yard includes a fenced area ideal for pets, gardening, or outdoor enjoyment. Located just minutes from Crisfield's waterfront, marina, restaurants, festivals, and ferry service to Smith Island, this home provides easy access to the Eastern Shore lifestyle. Whether you're looking for a primary residence, vacation getaway, or investment property, this home is full of potential. Property is being sold As-Is. Schedule your private showing today!

108 W Chesapeake Ave, Crisfield

Listing courtesy of EXP Realty, LLC. Contact:

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