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$549,000

Wake up to breathtaking views of Oyster Bay, sip your morning coffee as the sun rises over the marsh, and end each day watching spectacular sunsets from your private balcony. Perfectly positioned to capture the beauty of Chincoteague Island's coastal landscape, this furnished, turnkey waterfront retreat is ready for you to start enjoying island life from day one. Inside, soaring vaulted ceilings, abundant natural light, and an open-concept living area create an inviting space designed for gathering with family and friends. Expansive windows frame the ever-changing marsh and bay views, while the spacious living and dining areas flow seamlessly onto the large deck and screened porch—ideal for outdoor dining, relaxing with a book, or simply taking in the peaceful surroundings. The thoughtfully designed floor plan offers three bedrooms, including a spacious primary suite with its own private balcony overlooking Oyster Bay—the perfect place to unwind after a day on the water. Multiple outdoor living spaces allow everyone to enjoy the fresh coastal air, from the screened porch to the expansive deck and elevated viewing deck. Designed with water lovers in mind, the home also features an outdoor shower for rinsing off after a day at the beach or boating, generous storage beneath the home for kayaks, paddleboards, bicycles, fishing gear, and all your island toys, plus ample space to entertain inside and out. Whether you're searching for a full-time residence, vacation getaway, or investment opportunity, this move-in-ready Chincoteague retreat offers the perfect combination of comfort, coastal charm, and unforgettable Oyster Bay views. Just bring your suitcase—everything else is already here. Sold furnished and turn key. Currently a vacation rental named Assateague Breezes

3 Beds ⋅ 2 Baths

Wake up to breathtaking views of Oyster Bay, sip your morning coffee as the sun rises over the marsh, and end each day watching spectacular sunsets from your private balcony. Perfectly positioned to capture the beauty of Chincoteague Island's coastal landscape, this furnished, turnkey waterfront retreat is ready for you to start enjoying island life from day one. Inside, soaring vaulted ceilings, abundant natural light, and an open-concept living area create an inviting space designed for gathering with family and friends. Expansive windows frame the ever-changing marsh and bay views, while the spacious living and dining areas flow seamlessly onto the large deck and screened porch—ideal for outdoor dining, relaxing with a book, or simply taking in the peaceful surroundings. The thoughtfully designed floor plan offers three bedrooms, including a spacious primary suite with its own private balcony overlooking Oyster Bay—the perfect place to unwind after a day on the water. Multiple outdoor living spaces allow everyone to enjoy the fresh coastal air, from the screened porch to the expansive deck and elevated viewing deck. Designed with water lovers in mind, the home also features an outdoor shower for rinsing off after a day at the beach or boating, generous storage beneath the home for kayaks, paddleboards, bicycles, fishing gear, and all your island toys, plus ample space to entertain inside and out. Whether you're searching for a full-time residence, vacation getaway, or investment opportunity, this move-in-ready Chincoteague retreat offers the perfect combination of comfort, coastal charm, and unforgettable Oyster Bay views. Just bring your suitcase—everything else is already here. Sold furnished and turn key. Currently a vacation rental named Assateague Breezes

5466 Amrien Circle Dr, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600

$1,749,000

Experience exceptional waterfront living at this stunning Chincoteague Bay retreat, where panoramic bay views, spectacular sunsets, expansive outdoor living spaces, and an impressive private pier create the ultimate Eastern Shore lifestyle. Situated on a private waterfront setting, this remarkable property offers 5 bedrooms, 4.5 baths, over 4,000 square feet of living space, and a floor plan designed to maximize both comfort and breathtaking water views. A welcoming wrap-around porch sets the tone as you arrive, providing the perfect place to relax, entertain, and enjoy the coastal breeze. Inside, walls of windows frame sweeping views of Chincoteague Bay while beautiful hardwood floors, custom wood trim, solid wood doors, and extensive custom cabinetry showcase the home's quality craftsmanship. Throughout the home, thoughtful details reflect the property's coastal setting, including an original hand-painted mural by renowned Chincoteague artist Tracy Taylor featured in one of the guest bedrooms. The first floor offers a spacious family room with fireplace, a separate living room, a flexible office/den space, a full guest bathroom, and generous dining areas designed for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, a pantry, and seamless flow into the dining and living areas, making it ideal for both everyday living and entertaining. Nearly every gathering space is positioned to take advantage of the home's exceptional waterfront setting. The second floor features four bedrooms, including a luxurious waterfront primary suite with a vaulted ceiling, an expansive private balcony overlooking the bay, a massive walk-in closet, and a spa-inspired bath featuring a double vanity, soaking tub, separate tiled shower, and extensive custom cabinetry. Three additional guest bedrooms, a full hall bath, and a conveniently located laundry room complete the second level. The third floor serves as a private retreat featuring the fifth bedroom suite with its own full bath, walk-in closet, private waterfront balcony, and panoramic views across Chincoteague Bay. This level also provides access to substantial attic storage space. The outdoor amenities are truly exceptional. Enjoy multiple waterfront balconies, the expansive wrap-around porch, and a waterfront patio with fire pit overlooking the bay. A substantial private pier extends through the marsh to open water and features multiple docking areas with room for several boats, expansive sunning and swimming platforms, and endless opportunities for boating, fishing, crabbing, kayaking, paddleboarding, and entertaining on the water. From the home, porch, balconies, patio, and pier, enjoy breathtaking sunset views across Chincoteague Bay. Additional features include an attached 2-car garage with extra storage space, extensive attic storage, two storage sheds, and a large parking area for guests, boats, and recreational equipment. Rarely does a property combine this level of privacy, panoramic waterfront views, abundant living space, exceptional boating amenities, and spectacular sunset vistas. This is a truly remarkable opportunity to own one of Chincoteague's premier waterfront properties. Roof was replaced five years ago, first floor HVAC was replaced 2025 with a heat pump w/ propane pack, second floor HVAC was replaced a couple of years ago.

5 Beds ⋅ 5 Baths

Experience exceptional waterfront living at this stunning Chincoteague Bay retreat, where panoramic bay views, spectacular sunsets, expansive outdoor living spaces, and an impressive private pier create the ultimate Eastern Shore lifestyle. Situated on a private waterfront setting, this remarkable property offers 5 bedrooms, 4.5 baths, over 4,000 square feet of living space, and a floor plan designed to maximize both comfort and breathtaking water views. A welcoming wrap-around porch sets the tone as you arrive, providing the perfect place to relax, entertain, and enjoy the coastal breeze. Inside, walls of windows frame sweeping views of Chincoteague Bay while beautiful hardwood floors, custom wood trim, solid wood doors, and extensive custom cabinetry showcase the home's quality craftsmanship. Throughout the home, thoughtful details reflect the property's coastal setting, including an original hand-painted mural by renowned Chincoteague artist Tracy Taylor featured in one of the guest bedrooms. The first floor offers a spacious family room with fireplace, a separate living room, a flexible office/den space, a full guest bathroom, and generous dining areas designed for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, a pantry, and seamless flow into the dining and living areas, making it ideal for both everyday living and entertaining. Nearly every gathering space is positioned to take advantage of the home's exceptional waterfront setting. The second floor features four bedrooms, including a luxurious waterfront primary suite with a vaulted ceiling, an expansive private balcony overlooking the bay, a massive walk-in closet, and a spa-inspired bath featuring a double vanity, soaking tub, separate tiled shower, and extensive custom cabinetry. Three additional guest bedrooms, a full hall bath, and a conveniently located laundry room complete the second level. The third floor serves as a private retreat featuring the fifth bedroom suite with its own full bath, walk-in closet, private waterfront balcony, and panoramic views across Chincoteague Bay. This level also provides access to substantial attic storage space. The outdoor amenities are truly exceptional. Enjoy multiple waterfront balconies, the expansive wrap-around porch, and a waterfront patio with fire pit overlooking the bay. A substantial private pier extends through the marsh to open water and features multiple docking areas with room for several boats, expansive sunning and swimming platforms, and endless opportunities for boating, fishing, crabbing, kayaking, paddleboarding, and entertaining on the water. From the home, porch, balconies, patio, and pier, enjoy breathtaking sunset views across Chincoteague Bay. Additional features include an attached 2-car garage with extra storage space, extensive attic storage, two storage sheds, and a large parking area for guests, boats, and recreational equipment. Rarely does a property combine this level of privacy, panoramic waterfront views, abundant living space, exceptional boating amenities, and spectacular sunset vistas. This is a truly remarkable opportunity to own one of Chincoteague's premier waterfront properties. Roof was replaced five years ago, first floor HVAC was replaced 2025 with a heat pump w/ propane pack, second floor HVAC was replaced a couple of years ago.

5141 Fish Ln, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600

$829,500

NEW ISLAND LISTING! CHINCOTEAGUE COASTAL WATERFRONT at its finest in the sought-after Oyster Bay community. This custom-built waterfront home is perfectly positioned on a canal with breathtaking bay views and unforgettable sunrises over Assateague Island. Enjoy direct water access with your own private dock plus a floating dock ideal for kayaking, paddleboarding, crabbing, boating, and endless days on the water. Designed to embrace the views, the home offers spacious living areas along with large screened porches on both the front and back of the home, allowing you to take in stunning east and west water views along with refreshing coastal breezes. The first-floor primary suite provides convenient one-level living, while upstairs features two generously sized guest bedrooms, a full bath, and an open balcony overlooking the main living area below. Elevated on pilings, the ground level provides additional flexible living space currently used as a guest bedroom, along with an outdoor shower and abundant storage for all your beach and boating essentials. The oversized lot offers ample parking for vehicles, boats, trailers, and guests. Whether you are looking for a full-time waterfront retreat or the perfect coastal getaway, this home captures the best of life between the beach and the bay!

3 Beds ⋅ 2 Baths

NEW ISLAND LISTING! CHINCOTEAGUE COASTAL WATERFRONT at its finest in the sought-after Oyster Bay community. This custom-built waterfront home is perfectly positioned on a canal with breathtaking bay views and unforgettable sunrises over Assateague Island. Enjoy direct water access with your own private dock plus a floating dock ideal for kayaking, paddleboarding, crabbing, boating, and endless days on the water. Designed to embrace the views, the home offers spacious living areas along with large screened porches on both the front and back of the home, allowing you to take in stunning east and west water views along with refreshing coastal breezes. The first-floor primary suite provides convenient one-level living, while upstairs features two generously sized guest bedrooms, a full bath, and an open balcony overlooking the main living area below. Elevated on pilings, the ground level provides additional flexible living space currently used as a guest bedroom, along with an outdoor shower and abundant storage for all your beach and boating essentials. The oversized lot offers ample parking for vehicles, boats, trailers, and guests. Whether you are looking for a full-time waterfront retreat or the perfect coastal getaway, this home captures the best of life between the beach and the bay!

5344 Sunrise Dr, Chincoteague Island

Listing courtesy of Beach Bay Realty. Contact:

$998,000

Located in the sought-after Oyster Bay community on Chincoteague Island, this canal-front home offers sweeping views of the canal and Oyster Bay, creating a peaceful coastal setting from the moment you arrive. Enter through the bright and airy foyer and step into an open, welcoming living space highlighted by high ceilings and luxury vinyl plank flooring throughout. The kitchen is thoughtfully designed with quartz countertops, stainless steel appliances, and a casual bar area, flowing seamlessly into the living and dining spaces. Large windows frame the water views, while direct access to the expansive deck invites indoor-outdoor living. The deck is well-equipped for entertaining, including an exterior propane connection for a grill, making it easy to enjoy meals overlooking the canal. The main level features two bedrooms and a shared guest bathroom, along with a convenient laundry room. A dedicated office is located just off the living space and offers both canal views and direct access to the deck, providing a quiet and inspiring workspace. Upstairs, an open loft adds flexible living space and leads to a fourth bedroom that can easily function as a media room or bonus area. The primary suite is generously sized and opens to a private balcony with beautiful views of the canal and Oyster Bay. The en suite bathroom includes a large jetted tub, a walk-in tiled shower with rainfall showerhead, and ample space to unwind. Below the main living areas, an expansive unfinished basement provides exceptional storage capacity to accommodate virtually any need. Outside, enjoy bulkheaded canal access with a ladder allowing for boating, kayaking, and fishing directly from your property. Ideally located near Chincoteague’s charming shops, dining, and island attractions, with easy access to Assateague Island and its beaches and wildlife. Make this island home yours today!

4 Beds ⋅ 2 Baths

Located in the sought-after Oyster Bay community on Chincoteague Island, this canal-front home offers sweeping views of the canal and Oyster Bay, creating a peaceful coastal setting from the moment you arrive. Enter through the bright and airy foyer and step into an open, welcoming living space highlighted by high ceilings and luxury vinyl plank flooring throughout. The kitchen is thoughtfully designed with quartz countertops, stainless steel appliances, and a casual bar area, flowing seamlessly into the living and dining spaces. Large windows frame the water views, while direct access to the expansive deck invites indoor-outdoor living. The deck is well-equipped for entertaining, including an exterior propane connection for a grill, making it easy to enjoy meals overlooking the canal. The main level features two bedrooms and a shared guest bathroom, along with a convenient laundry room. A dedicated office is located just off the living space and offers both canal views and direct access to the deck, providing a quiet and inspiring workspace. Upstairs, an open loft adds flexible living space and leads to a fourth bedroom that can easily function as a media room or bonus area. The primary suite is generously sized and opens to a private balcony with beautiful views of the canal and Oyster Bay. The en suite bathroom includes a large jetted tub, a walk-in tiled shower with rainfall showerhead, and ample space to unwind. Below the main living areas, an expansive unfinished basement provides exceptional storage capacity to accommodate virtually any need. Outside, enjoy bulkheaded canal access with a ladder allowing for boating, kayaking, and fishing directly from your property. Ideally located near Chincoteague’s charming shops, dining, and island attractions, with easy access to Assateague Island and its beaches and wildlife. Make this island home yours today!

5403 Pearl Dr, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600

$285,000

BRING ALL OFFERS! Tucked away in a peaceful, nature-filled setting on beautiful Chincoteague Island, this charming 2-bedroom, 2-bath duplex offers the perfect blend of privacy, comfort, and island living. Surrounded by mature trees, marsh grasses, and a tranquil pond frequented by local wildlife, this hidden retreat feels worlds away from the everyday. Arrive via the spacious front deck and step inside to a bright, open floor plan designed for easy coastal living. The generous living room flows seamlessly into the dining area and kitchen, creating an inviting space for gathering with family and friends. Warm wood trim, abundant natural light, and a breakfast bar add to the home's welcoming character. French doors lead to a screened porch overlooking the pond and natural marsh landscape, providing the perfect spot to enjoy your morning coffee, unwind with a good book, or watch birds and wildlife in their natural habitat. The expansive front deck offers even more outdoor living space for entertaining, dining, or simply soaking in the peaceful surroundings. Upstairs, the spacious primary bedroom features its own private balcony with elevated views of the pond and surrounding greenery, creating a serene escape at the end of the day. A second generously sized bedroom and full bath provide comfortable accommodations for guests or family. The ground level includes a one-car garage with ample room for storage of beach gear, bicycles, kayaks, fishing equipment, and all the essentials for enjoying the island lifestyle. With multiple decks, a screened porch, beautiful natural views, and a quiet location tucked among the trees, this property offers a rare opportunity to enjoy the peaceful side of Chincoteague Island. Whether you're searching for a primary residence, vacation getaway, or investment property, this island retreat is ready to be enjoyed. Property is being sold As Is.

2 Beds ⋅ 2 Baths

BRING ALL OFFERS! Tucked away in a peaceful, nature-filled setting on beautiful Chincoteague Island, this charming 2-bedroom, 2-bath duplex offers the perfect blend of privacy, comfort, and island living. Surrounded by mature trees, marsh grasses, and a tranquil pond frequented by local wildlife, this hidden retreat feels worlds away from the everyday. Arrive via the spacious front deck and step inside to a bright, open floor plan designed for easy coastal living. The generous living room flows seamlessly into the dining area and kitchen, creating an inviting space for gathering with family and friends. Warm wood trim, abundant natural light, and a breakfast bar add to the home's welcoming character. French doors lead to a screened porch overlooking the pond and natural marsh landscape, providing the perfect spot to enjoy your morning coffee, unwind with a good book, or watch birds and wildlife in their natural habitat. The expansive front deck offers even more outdoor living space for entertaining, dining, or simply soaking in the peaceful surroundings. Upstairs, the spacious primary bedroom features its own private balcony with elevated views of the pond and surrounding greenery, creating a serene escape at the end of the day. A second generously sized bedroom and full bath provide comfortable accommodations for guests or family. The ground level includes a one-car garage with ample room for storage of beach gear, bicycles, kayaks, fishing equipment, and all the essentials for enjoying the island lifestyle. With multiple decks, a screened porch, beautiful natural views, and a quiet location tucked among the trees, this property offers a rare opportunity to enjoy the peaceful side of Chincoteague Island. Whether you're searching for a primary residence, vacation getaway, or investment property, this island retreat is ready to be enjoyed. Property is being sold As Is.

5160 Mallard Pond, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600