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$549,000
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
$1,462,000
4 Beds ⋅ 4 Baths
Waterfront one-of-a-kind on deep water! LOCATION MATTERS! Over 1 acre & 108' of DEEP-WATER FRONTAGE with PIER overlooking Assateague Island, this home offers AMAZING SUNRISES & gorgeous FULL MOONS shining on the water! PANORAMIC VIEWS! SPACIOUS Home for large families & get-togethers. 12X20 PRIVATE DOCK. almost 3,000 SF. Stone foundation. Large Master Ensuite w/ Lg Jacuzzi Tub, Walk-In Closet. Four Season Sunroom, See-Through fireplace. Attached TWO-CAR Attached GARAGE.(Storage over entire garage) Dual-zone heat pumps w/ wifi controls. Hot/Cold Outdoor shower. Home is 6.8' above water level. New Roof, Windows, & 2nd level deck in 2020. Strong VACATION RENTAL welcoming 12 people comfortably. Several OVERSIZED DECKS w/ BREATHTAKING VIEWS. Quiet neighborhood close to the PONIES of Assateague. Near boat ramp. Recent upgrades have been made. A MUST SEE HOME!

6107 Hopkins Ln, Chincoteague Island

Listing courtesy of Beach Bay Realty. Contact:

$489,990
3 Beds ⋅ 3 Baths
The Sea Spray is a lovely 3 bd, 2.5 ba home with plenty of space. The functional and stylish design offers a 1st floor primary bd with an en-suite bathroom. The main level also showcases a kitchen, separate dining room, living room and two porches. The upper level hosts 2 more bd, a full ba and an office space. This beautiful lot on Castaway Drive will not last long. It is the perfect spot to build your dream home in this water front community. Enjoy all that Captain's Cove has to offer. The many amenities include 2 outdoor pools & 1 indoor pool, tennis courts, the community marina & boat ramp, exercise room, the playground & restaurant at the Marina Club. Minutes to the beach! Just a short ride to Ocean City, MD, Chincoteague Island or Assateague Island. The home is to be built & the photos of the model home may include options. Taxes based on land only.

Lot 720 Castaway Dr, Greenbackville

Listing courtesy of Monument Sotheby's International Realty. Contact: (703) 838-9792
$649,000
3 Beds ⋅ 2 Baths
Island Living at Its Finest on South Main Street! Wake up to breathtaking panoramic views of the Chincoteague Channel and end each day with spectacular sunsets from this beautifully renovated water view retreat. Completely remodeled down to the studs, this turnkey 3-bedroom, 2-bath home features new electrical, plumbing, roof, and added Hardie Plank siding . Inside, you’ll find a first-floor bedroom and full bath, an inviting eat-in kitchen with soft-close cabinetry and drawers, plus a separate breakfast nook perfect for morning coffee with a view. The spacious enclosed front porch is the showpiece, offering front-row seats to the water, passing boats, and the world-famous Chincoteague pony swim parade while the ponies run right in front of the home. Outside, enjoy a fenced backyard, outdoor deck, outdoor shower, and a large storage shed for all your beach and boating gear. Offered fully furnished and turnkey, this established vacation rental is ready to continue generating income or become your own waterview escape. A rare opportunity to own a completely renovated home in one of Chincoteague’s most sought-after water view locations!

3238 Main St, Chincoteague Island

Listing courtesy of Beach Bay Realty. Contact:

$419,000
3 Beds ⋅ 2 Baths
Panoramic WATERVIEWS from this charming well maintained coastal home in the quaint waterfront village of Wachapreague, Virginia! Enjoy beautiful water views, refreshing coastal breezes, and the relaxed pace of small-town living from the inviting screened front rocking-chair porch. Inside, you’ll find a welcoming foyer with wood floors, French doors opening to the living room, tall ceilings, a formal dining room, and a spacious kitchen featuring beautiful wood cabinetry, tile backsplash, coffee side bar, dishwasher, and vented range hood. A large enclosed back porch, laundry and a full bath. Upstairs offers three bedrooms with wood flooring and a full bath, including a jetted tub, while several rooms enjoy spectacular water views. Situated on TWO Lots. Additional features include newer replacement tilt windows, dual-zone Trane heat pumps with central heat and air, Large back deck with composite decking, vinyl railings, screened front porch, whole house water softener, storage shed, and a charming historic summer kitchen. Just an easy stroll to the town marina, shops, & public boat ramp and marina, this home offers the perfect blend of historic character and modern comfort. A rare opportunity to own a piece of local history—once part of the renowned Colona family—with open rear water views. A must see home!

8 South St, Wachapreague

Listing courtesy of Beach Bay Realty. Contact:

$485,000
3 Beds ⋅ 2 Baths
Experience the charm of Chincoteague Island from this beautifully updated coastal retreat offering water views of Chincoteague Bay and spectacular sunset skies. Located on historic Main Street and sold fully furnished and turn-key, this thoughtfully renovated 3-bedroom, 2-bath home presents an exceptional opportunity as a primary residence, vacation getaway, or investment property. As you arrive, the welcoming covered front porch invites you to sit back, relax, and enjoy views of the bay just across the street. Inside, you'll discover a bright and spacious open-concept living area featuring luxury vinyl plank flooring, updated lighting, and a seamless flow between the living room, dining area, and beautifully refreshed kitchen. The kitchen offers abundant cabinetry, updated appliances, a custom butcher block island, and access to the rear screened porch and expansive deck, creating the perfect indoor-outdoor entertaining space. The main level also features a full bathroom and multiple outdoor living areas, including both front and rear screened porches and a large rear deck overlooking a private, tree-lined backyard retreat. Upstairs, the spacious primary suite features its own private balcony, while two additional bedrooms and a second full bath provide comfortable accommodations for family and guests. A second front balcony captures beautiful bay views and evening sunsets that make Chincoteague living so special. Over the past several years, the home has undergone extensive improvements, including new HVAC systems for both levels, luxury vinyl plank flooring throughout, renovated bathrooms, updated lighting, a new on-demand LP water heater, new appliances, new exterior doors, balcony improvements, a resurfaced screened porch, paved driveway, laundry room improvements, and numerous additional upgrades throughout the property. Located just moments from Chincoteague's restaurants, shops, fishing, boating, carnival grounds, and the natural beauty of the island, this fully furnished and meticulously maintained coastal home offers the perfect blend of comfort, convenience, and Eastern Shore charm. Whether you're seeking a year-round residence, vacation home, or income-producing rental property, this exceptional Main Street retreat is ready to be enjoyed from day one.

3566 Main St, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600
$630,000
4 Beds ⋅ 3 Baths
Welcome to waterfront living in Captain's Cove Golf & Yacht Club! Perfectly positioned on a canal-front lot with beautiful water views, this thoughtfully designed coastal home offers the ideal blend of comfort, functionality, and Eastern Shore lifestyle. Built in 2021, the elevated construction provides abundant covered parking, storage, and outdoor living space below, while the interior floor plan is designed for easy everyday living and entertaining. Step inside the main level and discover a private primary suite featuring a walk-in closet and en-suite bath, along with two additional bedrooms, a full hall bath, and the convenience of a dedicated laundry room. The spacious screened porch overlooking the canal creates the perfect spot for morning coffee, evening cocktails, or simply enjoying the waterfront setting. Upstairs, the home opens into a bright and expansive living area where oversized windows capture stunning water views throughout the main living spaces. The beautifully appointed kitchen features stainless steel appliances, granite countertops, abundant cabinetry, a large center island with seating, and a generous walk-in pantry. The open dining and living areas flow seamlessly together, creating an inviting space for gatherings large and small. A fourth bedroom and third full bath on this level provide excellent flexibility for guests, a home office, or multi-generational living. Step outside onto the oversized waterfront balcony deck to enjoy panoramic canal and water views. Outside, this property is designed to fully embrace the waterfront lifestyle. Enjoy your private bulkheaded canal frontage with direct water access, a spacious waterside entertaining area, outdoor shower, and a detached storage shed for all your boating, fishing, kayaking, and beach gear. The expansive covered parking and storage area beneath the home offers room for multiple vehicles, golf carts, water toys, and workshop space. Located within the amenity-rich Captain's Cove Golf & Yacht Club community, owners enjoy access to an indoor and outdoor pool, marina, boat ramp, golf course, clubhouse restaurant, fitness center, playgrounds, pickleball courts, and more. Whether you're searching for a full-time residence, vacation getaway, or investment property, this exceptional canal-front home delivers the best of coastal living on Virginia's Eastern Shore.

3272 Salty Way, Greenbackville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600
$1,749,000
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
$535,000
3 Beds ⋅ 2 Baths
You will LOVE the views! Enjoy beautiful views of Chincoteague Bay from this well-maintained coastal home in the desirable Bay Colony community. Situated on a spacious lot, this elevated 3-bedroom, 2-bath home offers the perfect blend of island charm, comfortable living, and outdoor enjoyment. Designed to take advantage of the surrounding scenery, the home features multiple covered porches, balconies, a screened porch, and expansive wraparound decking, providing numerous places to relax, entertain, and enjoy the coastal breezes. Bay views can be enjoyed from multiple areas of the home, creating a true island retreat. Inside, the upper level serves as the heart of the home, featuring an open-concept kitchen, dining area, and family room filled with natural light. The kitchen offers stainless steel appliances, abundant cabinetry, breakfast bar seating, and seamless flow into the living and dining spaces, making it ideal for everyday living and entertaining. Sliding doors lead to the screened porch, creating an inviting extension of the living area. The thoughtfully designed floor plan includes a spacious first-floor primary bedroom with direct access to the covered porch, an additional first-floor guest bedroom and full bath, plus a private upstairs bedroom and full bath with balcony access. A dedicated laundry area adds convenience, while tile flooring throughout the main living areas enhances the home's easy-care coastal appeal. Additional features include vinyl siding, public water, private septic, detached storage shed, enclosed under-house storage, and an outdoor shower—perfect for rinsing off after a day at the beach or on the water. Being sold furnished with appliances included, this move-in-ready property offers a turnkey opportunity as a primary residence, vacation getaway, or investment property. Conveniently located near Chincoteague's shops, restaurants, marinas, wildlife refuge, and Assateague Beach, this is your opportunity to experience the very best of island living with beautiful bay views and easy access to everything the island has to offer.

5061 Bay Colony Ln, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600
$840,000
4 Beds ⋅ 3 Baths
Thoughtfully designed and built with attention to detail, this custom home, located in beautiful Captains Cove, is situated on a corner lot with water views from every room. The perfect marriage of form and function. Watch the sunrise over the Chincoteague bay and set over the canal. This home boasts almost 2,700 square feet of living space with 4 spacious bedrooms and 3 full bathrooms including a massive primary suite, that features a walk in tile shower, large soaking tub, rear deck access, and dual closets. This home was designed for efficiency with dual zone heat pumps, with propane back up, and a cozy pellet stove. Sturdy 2X10 floor joists and Luxury Vinyl Plank flooring add durability and reduce maintenance. The kitchen is equipped with a 6 burner gas stove, double oven, black stainless steel appliances, beautiful quartz counter tops, a decorative tile back splash, ample cabinet space and a large walk-in pantry, making it a chef's delight. The ground level was very well thought-out with 2 remote controlled garage doors, a workshop area, utility room and dual barn doors that open up to a concrete patio with outdoor shower along the canal front, allowing the breezes from the bay to cool things off in the Summer. The ground level offers indoor parking for multiple vehicles while still having plenty of space for your toys, bikes, and golf cart for exploring the amenity rich community that features golf, pickle ball, tennis, indoor pool, fitness room, 2 outdoor pools and the Marina Club Restaurant. This stunner has a variety of outdoor spaces to choose from for entertaining and relaxing. There are 3 open deck areas, each with their own inviting characteristics whether you want to sun, relax in the shade, or lounge with a book. Additionally there is a large screened porch that makes a perfect outdoor dining space without the hassle from uninvited pests. Last but not least, the viny bulkhead is only 5 years old and the 7,000 lb boat lift will keep your boat high and dry reducing costly maintenance and giving you peace of mind. This home is truly a must see. Most furnishings can convey at no additional cost with an acceptable offer. Minimal exclusions will be provided prior to ratification if desired.

3352 Scimitar Way, Greenbackville

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$319,900
3 Beds ⋅ 2 Baths
Seller is Offering $5,000.00 Toward Purchaser's Closing Costs! Experience refined coastal living in the sought after Waterfront Community of Captain’s Cove, where lifestyle and craftsmanship come together. This brand new Ranch style Beracah Home showcases the Buckley model is an elegant single level design offering 3 bedrooms, 2 baths, and nearly 1,400 square feet of beautifully curated living space. Thoughtfully designed with an open concept layout, the home features a seamless flow between the kitchen, dining, and living areas perfect for entertaining or relaxed coastal living. Quality construction is evident throughout, with 2x6 exterior framing, enhanced insulation, and energy efficient systems designed for both comfort and longevity. Positioned within one of the Eastern Shore’s premier resort style communities, residents of Captain’s Cove enjoy access to a golf course, marina, indoor and outdoor pools, fitness center, and an array of recreational amenities. Whether you’re seeking a primary residence, luxury retreat, or investment property, this home offers an exceptional opportunity to enjoy the best of coastal Virginia living.

37348 Doubloon Dr, Greenbackville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 6676612000
$319,900
3 Beds ⋅ 2 Baths
Seller is Offering $5,000.00 Toward Purchaser's Closing Costs! Stylish coastal living meets smart design in this move-in-ready 3-bedroom, 2-bath home offering 1,395 sq ft of thoughtfully planned space. A light-filled, open concept great room flows into the dining area and kitchen, creating a seamless entertaining zone where family meals and weekend gatherings feel effortless. Large windows and neutral, modern finishes create an airy, welcoming backdrop that’s easy to personalize. Kitchen highlights: generous counterspace, abundant cabinetry for organization, and an efficient layout that keeps cooking and cleanup convenient. The adjacent dining area provides direct access to the outdoor area perfect for morning coffee or grilling on warm evenings. Primary suite: a private retreat with generous closet space and a spa-inspired en-suite bath featuring a contemporary vanity and well appointed fixtures. Two additional bedrooms offer flexible options for guests, a home office, or a hobby room. A second full bath is conveniently located for family and visitors. Practical amenities include dedicated laundry space, ample storage throughout, and an attached garage for secure vehicle parking and extra storage. Low maintenance landscaping and a modest yard make upkeep simple while offering outdoor relaxation space. Located in a tranquil neighborhood with easy access to coastal attractions, local services, and commuter routes, this home blends thoughtful finishes with everyday functionality. Schedule a showing today.

37322 Doubloon Dr, Greenbackville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 6676612000
$829,500
3 Beds ⋅ 2 Baths
Waterfront Gem with Pier & Sunset Views! Discover the charm of island living w/ this adorable bayfront cottage, perfectly positioned on two parcels—one featuring the home and the other offering direct waterfront access with a private pier and dock complete with a built-in surround bench, ideal for soaking in breathtaking sunset views over the bay. Full of character & classic coastal charm with modern touches. Original hardwood plank flooring, a beautifully updated kitchen with granite countertops, both first and second-floor bedrooms & baths for flexible living. Wake up to serene bay views from the bedroom’s charming bay windows. Enjoy the outdoors from both front & rear screened porches-Great Coastal Breezes. Secluded & Peaceful setting. Large Shed. Pond in Back. Freshly Painted Home.

5174 Winder Ln, Chincoteague Island

Listing courtesy of Beach Bay Realty. Contact:

$649,000
3 Beds ⋅ 2 Baths
Phenomenally maintained 1.5 story beach cottage. 3BR 2BA with vaulted ceilings. Office/Den/Bonus Room setup on the second floor. 1st Floor Ensuite w/ Walk In Closet & Bath w/ tiled shower. Shiplap walls, SS Appliances. Quartz counters, Butcher block Kitchen Island. Luxury Vinyl Plank Flooring. Ceramic Tile in Baths. Nice Back Porch w/ large outdoor enclosed shower. Detached garage finished w/ epoxy floor. Fantastic Backyard Space w/Stonework & Lighting w/Hot Tub and Privacy Fence. Rennai Tankless Water Heater & Plenty of parking space for vehicles and boats. Located on Chincoteague Island in a great Beach Cottage Community just minutes from Assateague beaches, fishing and coastal living at its finest. Property can be accessed from two streets. A MUST SEE! Sold Unfurnished.

7017 Josephine Ln, Chincoteague Island

Listing courtesy of Beach Bay Realty. Contact:

$2,350,000
8 Beds ⋅ 6 Baths
Along a quiet stretch of Virginia’s Eastern Shore, where the Chesapeake Bay opens wide to endless horizon, lies Thickett Point, a 44.95± acre waterfront estate defined by privacy, scale, and potential. Set along a commanding reach of shoreline, this rare offering captures the essence of coastal living—expansive bay views, estuarian marshland, and a landscape shaped by water, light, and time. With no conservation easement in place, the property offers an uncommon level of freedom and long-term control rarely found among Chesapeake Bay holdings. At the heart of the estate are two distinct waterfront residences—Sunset House and Bayview House—each thoughtfully positioned to embrace the surrounding landscape and water views. Both homes are offered fully furnished, allowing for an immediate, seamless transition for personal use or continued short-term rental operation. Sunset House is oriented to the west, where each evening unfolds in panoramic color across the Bay. Designed with a relaxed coastal aesthetic, it offers an intimate and refined retreat—ideal for quiet escapes and elevated guest experiences. Bayview House reflects the character and charm of the Eastern Shore, with a more traditional design and a larger footprint suited for gatherings, extended stays, and multi-generational living. Together, the homes create a rare and highly functional composition—one that supports both private enjoyment and hospitality-driven income. The property is currently operated as a successful short-term rental, generating average annual income exceeding $100,000, while still allowing for personal use and flexibility. Beyond its current use, Thickett Point offers significant future upside, with identified utility expansion possibilities that present opportunities for further enhancement, additional improvements, or long-term strategic vision. The land itself is as compelling as the residences—nearly 45 acres of shoreline, marsh, and natural wildlife habitat. Owners and guests enjoy private beach access, kayaking along the Bay, hunting, fishing and crabbing just steps from shore, and the ever-changing presence of coastal wildlife across the surrounding marsh. Despite its sense of seclusion, the property is located just minutes from the historic town of Onancock—home to marinas, fine dining, galleries, and ferry access to Tangier Island—offering a seamless blend of privacy and accessibility. Thickett Point is more than a waterfront property—it is a fully furnished, turn-key Chesapeake Bay estate, offering the rare ability to live, host, invest, and create lasting value from day one.

24227 Thicket Point Ln, Onancock

Listing courtesy of The Land Group. Contact: (410) 934-3478
$438,750
3 Beds ⋅ 2 Baths
Wake up to breathtaking, unobstructed views of Chincoteague Bay from this exceptional 3-bedroom, 2-bath canal-front home, where nearly every room captures a stunning waterfront vista. Perfectly positioned with approximately 65 feet of private waterfrontage, this property offers the ideal blend of comfort, coastal charm, and boating lifestyle. The main living level welcomes you with a warm and inviting living room featuring a cozy pellet stove and expansive water views. The adjoining dining area overlooks picturesque Swan Gut, creating the perfect setting for meals with a view. The spacious kitchen offers abundant cabinetry, a breakfast bar, and ample workspace for entertaining family and friends. Also on the main level are a generously sized bedroom and a full bathroom. Sliding glass doors from both the living room and bedroom open onto a large, newly constructed composite deck, providing seamless indoor-outdoor living and the perfect place to enjoy spectacular sunrises, sunsets, and passing wildlife. Upstairs, the waterfront primary bedroom is a true retreat, complete with a private balcony overlooking the bay. A second guest bedroom, loft area ideal for a home office or additional sleeping space, and a second full bathroom complete the upper level. The ground level features an enclosed patio, utility room, and covered concrete parking, offering plenty of storage for your boating and outdoor gear. Whether you're searching for a year-round residence, vacation getaway, or waterfront investment, this remarkable home delivers panoramic water views, direct canal access, and an unbeatable coastal lifestyle in one of the Eastern Shore's most desirable waterfront communities.Located in the amenity-rich Captains Cove community offering golf, pools, waterfront dining, boat launch, fitness center, pickleball, playground, and more.

3402 Starboard St, Greenbackville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 6676612000
$375,000
3 Beds ⋅ 3 Baths
Welcome to this charming coastal-style home located in the sought-after Captain’s Cove Golf & Yacht Club community in Greenbackville, VA. Offering 3 bedrooms, 2.5 baths, and versatile living spaces, this inviting home blends comfort, natural light, and the relaxed lifestyle of Virginia’s Eastern Shore. A welcoming covered front porch sets the tone as you arrive, creating the perfect place to enjoy morning coffee or unwind in the evening. Inside, the spacious living room features soaring vaulted ceilings and beautiful Palladian windows that fill the home with natural light and create an open, airy feel. A cozy gas fireplace adds warmth and character, making the space ideal for both relaxing and entertaining. The kitchen and adjoining dining area provide a functional layout with great flow into the main living space, perfect for everyday living and hosting friends and family. Conveniently located on the main level, the private primary suite offers comfort and ease with its own en-suite bathroom. Upstairs, a loft overlooks the living room and creates additional living space, while two generously sized bedrooms, a full bathroom, and a bonus room provide flexibility for a home office, guest space, hobby room, or playroom. Step outside to the screened-in porch overlooking a peaceful wooded backyard, offering a serene setting for outdoor dining, relaxing, or enjoying nature. An outdoor shower is perfect after a day on the water or exploring nearby beaches, and the attached two-car garage provides ample storage for vehicles, tools, and recreational gear. As a resident of Captain’s Cove, you'll enjoy access to a wide range of amenities, including a waterfront golf course, indoor and outdoor pools, marina with boat launch and slips, waterfront restaurant and tiki bar, fitness center, basketball and pickleball courts, playgrounds, walking paths, and a variety of community activities and events. Ideally located just a short drive from Chincoteague Island and Assateague Island National Seashore, this home offers easy access to beaches, boating, fishing, wildlife refuges, and the famous wild ponies. Whether you're searching for a full-time residence, vacation retreat, or investment property, this home offers an exceptional opportunity to enjoy the best of coastal living on Virginia’s Eastern Shore.

37323 Davey Jones Blvd, Greenbackville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600
$459,000
3 Beds ⋅ 2 Baths
Waterfront living awaits in the amenity-rich Captain’s Cove Golf & Yacht Club! This charming elevated coastal cottage is perfectly situated on a bulkheaded canal-front lot with beautiful water views and direct access for boating, kayaking, paddleboarding, and fishing — offering the ultimate Eastern Shore lifestyle. Inside, the bright and airy open floorplan features luxury vinyl plank flooring throughout and inviting coastal character. The spacious kitchen and dining area flow seamlessly into the expansive family room with soaring cathedral ceilings, abundant natural light, and a cozy propane corner fireplace. Added in 2019, the oversized family room and screened porch significantly expanded the living space while maximizing the home's connection to the waterfront setting. French doors lead to the screened porch overlooking the canal — the perfect spot to enjoy morning coffee, evening sunsets, and refreshing coastal breezes. Outdoor living shines with multiple spaces designed for relaxing and entertaining. Beneath the screened porch, a large covered patio creates an ideal shaded retreat for gatherings, grilling, or unwinding after a day on the water. The level grassy backyard extends to the bulkheaded canal frontage, providing easy access to the water and plenty of room for outdoor enjoyment. The ground level includes a spacious two-car garage plus a finished studio/workspace ideal for a home office, hobby room, workshop, fitness space, or additional storage. The main level offers a flexible bedroom perfect for guests, an office, or den, along with a full bath and oversized laundry room. Upstairs, two generously sized bedrooms feature walk-in closets and share a convenient half bath, creating comfortable accommodations for family and visitors alike. Partially furnished and move-in ready, this property offers an easy transition to waterfront living. The boat is also negotiable, creating a rare turnkey opportunity to immediately begin enjoying life on the water. Captain’s Cove residents enjoy an impressive array of resort-style amenities including a golf course, marina, boat ramp, indoor and outdoor pools, fitness center, restaurant, pickleball, playgrounds, walking trails, and more.

3290 Scimitar Way, Greenbackville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600
$998,000
3 Beds ⋅ 4 Baths
Premier Chincoteague Bay waterfront with private dock, wide open bay views, breathtaking sunsets, and 1.45 acres in sought-after Smuggler’s Cove! This beautifully designed custom home offers exceptional coastal living surrounded by sweeping water views and incredible natural beauty. Inside, the home features vaulted ceilings, abundant natural light, a spacious kitchen, and a large dining space perfect for gathering with family and friends. Comfortable living areas and a cozy gas fireplace create a welcoming place to relax after a day on the water. A private studio/office located in a separate area of the home provides flexible space ideal for working, creating, or potentially transforming into a separate apartment or additional living space. The owner’s suite is a peaceful retreat with its own waterfront deck, two walk-in closets, and a spacious bath. Two additional guest bedrooms and a full bath offer comfortable accommodations for family and visitors. Outdoor living is truly special with a screened porch, open deck, and private dock along Chincoteague Bay—perfect for boating, kayaking, fishing, crabbing, or simply enjoying spectacular sunsets and wide open water views. The expansive property offers privacy and a front-row seat to the island’s incredible wildlife, including migratory birds and the natural beauty that makes nearby Assateague so special. Additional highlights include a large garage with EV charging station and an adjacent ground-level storage space ideal for water gear, tools, or workshop use. Recent roof and HVAC upgrades complete this exceptional waterfront offering. This is more than a home — it’s a lifestyle. Waterfront. Private. Unforgettable.

4443 Shady Ln, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600
$359,000
2 Beds ⋅ 2 Baths
Secluded island charm meets in-town convenience on Chincoteague Island. Tucked away yet just moments from the shops, restaurants, parks, waterfront, and everyday amenities of downtown, this delightful 2-bedroom, 1½-bath Colonial offers the rare combination of privacy, flexibility, and an exceptional location. The welcoming main level features a spacious living room filled with natural light, warm wood flooring, and recessed lighting—ideal for both relaxing and entertaining. The large eat-in kitchen is rich with character, showcasing knotty pine cabinetry and generous space for gatherings. A dedicated office/laundry room adds versatility for remote work, hobbies, or everyday convenience. Upstairs, both bedrooms feature vaulted ceilings with exposed beams, creating architectural interest and a cozy coastal-cottage feel that perfectly complements the island setting. Outside is where this property truly stands out. Set on a double lot, the expansive fenced yard offers endless possibilities for outdoor living, gardening, expansion, or future enhancements. Enjoy evenings on the rear deck or take advantage of the bonus cottage, complete with a screened porch and a flexible entertainment/storage building—ideal as a guest retreat, studio, workshop, or creative space. The owner has completed extensive exterior improvements, enhancing curb appeal and long-term value, allowing the next owner to move in and immediately enjoy the best of island living. Whether you’re searching for a full-time residence, a weekend getaway, or an investment opportunity, this property delivers location, versatility, and character—all just minutes from everything downtown Chincoteague has to offer.

4145 Hur Ln, Chincoteague Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600
$589,500
4 Beds ⋅ 3 Baths
Nestled along a tranquil canal, this lovely 4 bd, 3 ba piling home in Captain’s Cove offers the perfect blend of comfort & coastal charm. Inside the open-concept layout connects the kitchen, dining & living areas, forming the heart of the home & showcasing beautiful water views, ideal for entertaining or relaxing. Two bedrooms & a full bath are located on the 1st floor, while the 2nd floor features 2 more beds & baths, including a spacious primary suite. All bedrooms boast hardwood floors, adding warmth & elegance. Enjoy time outside on one of the two spacious decks. You have direct views of the launch pads at Wallops Island from the front porch! A convenient lift provides easy access from the ground to the first floor. Enjoy the peaceful waterfront lifestyle Captain’s Cove is known for.

3375 Anchor Ct, Greenbackville

Listing courtesy of Monument Sotheby's International Realty. Contact: (703) 838-9792
$285,000
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