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2474 Dry Dock Ct, Greenbackville
$392,990
4 Beds ⋅ 3 Baths
Ruby C Elevation offered by Gemcraft Homes CC LLC New Construction. Two -Story single-family home, 4BR/2.5 BA, 2217 sq ft, 2-car garage, 12 x 12 composite deck. The openness of the first level offers plenty of space for entertaining for the whole family to enjoy. Large open kitchen layout w/plenty of cabinets, kitchen island, granite countertops, deep pantry, SS Appliances. Optional Library, Second level features Owners Suite w/large Walk-in Closet, 4 BR's. and Loft. Pictures may have upgraded features/options not included in base price. Currently Under Construction, expected to be completed November 2026. Call for more information and your private showing. Captains Cove Golf & Waterfront Community amenities offer: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball, Tennis & Pickle-Ball Courts, Playground, Walking & Biking Trails, Picnic Area, Dog Park, Security and so much more. Captains Cove is located on Virginia's Eastern Shore and conveniently located close to major Metropolitan Areas along the East Coast. Within 3 Hours of Baltimore MD/Washington DC/Philadelphia PA, 5 hours from New York, 1 Hour from Ocean City MD, 2 hours from Virginia Beach/Norfolk/Hampton VA and only 20 minutes from the notorious Chincoteague Island VA.

2474 Dry Dock Ct, Greenbackville

Listing courtesy of Hall Realty. Contact:

5190 Pine Tree Way, Chincoteague Island
$515,000
3 Beds ⋅ 2 Baths
Experience the relaxed coastal lifestyle of Chincoteague Island in this beautifully reimagined elevated home, tucked away on a cul-de-sac in the desirable Oyster Bay II community. Completely gutted and renovated approximately three years ago, the home was transformed from the inside out with updated finishes, fixtures, appliances, and furnishings, giving it the fresh, polished feel of a much newer home. Step inside to bright, open living spaces highlighted by soaring vaulted ceilings and abundant natural light. The spacious great room flows seamlessly into the updated kitchen featuring granite countertops, stainless steel appliances, a farmhouse sink, subway tile backsplash, and a large peninsula with bar seating. The adjoining dining area provides a welcoming space for everyday meals and entertaining. The functional floor plan features a private primary suite and two additional bedrooms served by a second full bath. Vaulted ceilings enhance the home's open, airy feel, while thoughtful updates throughout create a cohesive, comfortable interior that's truly ready to enjoy. Outdoor living is just as inviting, with multiple composite decks, a patio, and an enclosed outdoor shower that's perfect for rinsing off after a day at the beach, boating, or fishing. A storage shed provides convenient space for bicycles, fishing gear, beach chairs, and other outdoor essentials. Sold furnished and turnkey, this beautifully updated home delivers the feel of a practically new home in an established Chincoteague location—simply arrive, unpack, and start enjoying island life. Ideal as a primary residence, vacation retreat, or investment property, it's conveniently located just minutes from Chincoteague's beaches, marinas, restaurants, shops, and the Chincoteague National Wildlife Refuge.

5190 Pine Tree Way, Chincoteague Island

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

Wolfridge Ln Unit LOT 119, Horntown
$68,000
It is the first time in the market; located in a serene setting at the end of a quiet cul-de-sac, this 3.52 acres lot offers a private and peaceful setting with minimal through traffic - ideal for families seeking both safety and tranquility. The distinctive shaped layout provides a wide front yard with colorful trees while maximizing backyard space, perfect for outdoor living and added privacy. Additional highlights include; reduced noise, a welcoming neighborhood atmosphere, and convenient access to Spectrum cable TV and electricity already available on-site. Build your dream home in this prestigious waterfront gated community. This beautiful partially The wooded lot is just over 3.52 acres. Amenities include a Community Center with two guest suites and workout room, a large pool with hot tub, new marina with boat ramp, dock and 25 boat slips. Come explore the other side of Chincoteague Bay!

Wolfridge Ln Unit LOT 119, Horntown

Listing courtesy of Keller Williams Realty Delmarva. Contact:

3238 Main St, Chincoteague Island
$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:

1156 Aft Ct, Greenbackville
$341,990
4 Beds ⋅ 3 Baths
The Hamilton offered by Gemcraft Homes at Captains Cove. As you walk into the Hamilton there is a Choice Room that's open to the foyer. Use this space as a formal living room or playroom for the kids. Down the hall is the Great Room. Add an optional fireplace to make an inviting space to gather with the whole family. The Great Room opens up to a classically designed Kitchen. A small Mudroom at the entry to the Garage rounds out this flexible first floor. Following the stairs, to the second floor, you find the Owner's Suite and three additional Bedrooms, all with ample closet space, plus a Laundry Room, centrally located at the end of the hallway for convenience and ease. The Owner's Suite with a spacious bedroom offers a walk-in closet brimming with storage space. Designed to be a private haven, the Owner's Bedroom has an ensuite bath with available options of a Super Bath, with soaking tub and shower, or Venetian-style, with a large glass-enclosed shower with seat. Take the Hamilton design even further with a variety of options, extensions, and upgrades to personalize this dream home. Conditioned crawl space for extra storage. Pictures may have upgraded features. Call today for your private showing. Home is "TO BE BUILT" Captains Cove Golf & Waterfront Community amenities offer: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball & Pickle-ball Courts, Playground, Walking & Biking Trails, Picnic Area, Dog Park, Security and such much more. Call today for your private showing. Captains Cove is located on Virginia's Eastern Shore and conveniently located close to major Metropolitan Areas along the East Coast. Within 3 Hours of Baltimore MD/Washington DC/Philadelphia PA, 5 hours from New York, 1 Hour from Ocean City MD, 2 hours from Virginia Beach/Norfolk/Hampton VA and only 20 minutes from the notorious Chincoteague Island VA.

1156 Aft Ct, Greenbackville

Listing courtesy of Hall Realty. Contact:

8 South St, Wachapreague
$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:

832 Amidship Dr, Greenbackville
$326,990
3 Beds ⋅ 2 Baths
The Emerald Model Elevation "C" offered by Gemcraft Homes. Modern Ranch Style Home. Single level living at its best! Featuring 3 BR/2 full BA & 2 Car garage. The well equipped kitchen is ready for entertaining and cooking comforting meals for family and friends. An open breakfast area and a breakfast bar expand the dining space for entertaining in the centrally located Great Room. A generous owners suit with a walk in closet and private bath with a large shower is located in the rear of the home. Two additional bedrooms are situated to the front of the home off a short alcove hallway with a hall bath. Conditioned crawl space for extra storage. Pictures may have upgraded features. Call today for your private showing. Captains Cove Golf & Waterfront Community amenities offer: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball & Pickle-ball Courts, Playground, Walking & Biking Trails, Picnic Area, Dog Park, Security and such much more. Call today for your private showing. Captains Cove is located on Virginia's Eastern Shore and conveniently located close to major Metropolitan Areas along the East Coast. Within 3 Hours of Baltimore MD/Washington DC/Philadelphia PA, 5 hours from New York, 1 Hour from Ocean City MD, 2 hours from Virginia Beach/Norfolk/Hampton VA and only 20 minutes from the notorious Chincoteague Island VA.

832 Amidship Dr, Greenbackville

Listing courtesy of Hall Realty. Contact:

884 Broadside Dr, Greenbackville
$371,990
3 Beds ⋅ 3 Baths
Frankford Model Elevation A offered by Offered by Gemcraft Homes New Construction. A unique twist on a traditional design that includes 3 bedrooms (optional 4th), 2.5 baths,1979 sq ft.w/2-car garage, two-story, family room, kitchen/breakfast room combination, and separate formal dining room. First floor laundry and first floor owner's suite with walk-in closet Second level offers 2 Additional BR's and full BA overlooking Main Living Area below. Optional Elevations available to add your own personal touch. Pictures may have upgraded features/options not included in base price. Home is "TO BE BUILT". Additional elevations and options are available to design your own customized home with all your personal touches. Call for mare information and your private showing. Captains Cove Golf & Waterfront Community amenities offer: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball & Pickle-Ball Courts, Playground, Walking & Biking Trails, Picnic Area, Dog Park, Security and so much more. Captains Cove is located on Virginia's Eastern Shore and conveniently located close to major Metropolitan Areas along the East Coast. Within 3 Hours of Baltimore MD/Washington DC/Philadelphia PA, 5 hours from New York, 1 Hour from Ocean City MD, 2 hours from Virginia Beach/Norfolk/Hampton VA and only 20 minutes from the notorious Chincoteague Island VA.

884 Broadside Dr, Greenbackville

Listing courtesy of Hall Realty. Contact:

3272 Salty Way, Greenbackville
$620,000
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:

3077 Navigator Dr, Greenbackville
$349,000
3 Beds ⋅ 2 Baths
Custom Built Single-story home located on a Pristine Golf Course in Captains Cove located in Greenbackville VA. Featuring 3 BR, 2 full baths, LVP throughout, separate laundry area, and a 2-car garage, this plan is ideal for low-maintenance living. Step inside to an open floor plan, the great room features tray ceilings and a fireplace that flows seamlessly into the kitchen and dining area. Whether you're hosting holiday meals or enjoying a cozy night in, this open-concept layout brings people together without feeling crowded. The kitchen offers granite countertops, breakfast bar, SS appliances, soft close drawers and a walk-in pantry. The rear foyer connects the garage and mud room, great for kicking off muddy boots after a day on the boat. The primary suite is tucked privately on one side of the home, featuring tray ceiling, large walk-in closet and en suite bath, with double bowl sink, soaking tub and stand-up shower. The other side of the home offers, two secondary bedrooms and a full bath. perfect for guests or a home office setup. Large concrete front porch and oversized rear concrete porch (10x28) perfect for relaxing, entertaining or enjoying the golf course views of the 6th Tee & Fairway. This is one of the largest golf course lots, Every square foot of this design is thoughtfully used, with minimal wasted space. Captains Cove Golf & Waterfront Community is the fastest growing Golf & Waterfront Community on the Eastern Shore of VA, Amenities offered: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball & Pickle-ball Courts, Playground, Picnic Area, Dog Park, Biking & Walking Trails, Security and more. Call for your private showing!

3077 Navigator Dr, Greenbackville

Listing courtesy of Hall Realty. Contact:

5141 Fish Ln, Chincoteague Island
$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:

Lot 26 Holly, Onancock
$359,000
3 Beds ⋅ 2 Baths
The Shelly is an inviting 1,532-square-foot ranch style home that offers thoughtful design and genuine comfort in historic Onancock, Virginia located on a private 0.92-acre lot bordering a serene creek. With three bedrooms and two full bathrooms, the home features a smart layout that places the primary suite on one side for privacy, while the two additional bedrooms sit on the opposite end. At the heart of the home, you'll find an open floor plan where the kitchen, living, and dining areas flow together—perfect for everyday living and gathering with loved ones. Step outside to enjoy both a welcoming front porch and a private back porch, ideal for morning coffee or evening relaxation. The two-car garage adds convenience, while the home's single-level design makes everything easily accessible. Located in the charming, historic town of Onancock, within walking distance to Onancock's charming downtown area where you'll find shops, restaurants, and community events. The property is also near Chesapeake Bay for fun water activities and close to Riverside Shore Memorial Hospital. This property offers small-town character with thoughtful modern living space. Taxes are based on assessed value of land only. To be built & photos of the model home may include options.

Lot 26 Holly, Onancock

Listing courtesy of Monument Sotheby's International Realty. Contact:

2353 Yardarm Dr, Greenbackville
$349,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained and extensively updated ranch home in Captain's Cove Golf & Yacht Club, offering over 1,800 square feet of comfortable one-level living, exceptional outdoor entertaining space, and resort-style amenities. Inside, the spacious living room features hardwood flooring, vaulted ceilings, a gas fireplace, and French doors leading to the expansive rear deck. The oversized kitchen and dining area offer abundant white cabinetry, quartz countertops, stainless steel appliances, updated lighting, and a center island with seating. A bright sunroom provides additional space to relax and enjoy backyard views. The split-bedroom floor plan offers privacy, with a spacious primary suite featuring vaulted ceilings, a walk-in closet, private deck access, and an ensuite bath with dual vanities, jetted soaking tub, and separate shower. Two additional bedrooms and a full bath complete the layout. Outdoor living is a highlight, with a large screened porch, expansive rear deck with grilling area, fenced backyard, and mature privacy landscaping. An attached two-car garage and storage shed provide additional space for vehicles and hobbies. Recent improvements include a brand-new roof, completed shed updates, HVAC replacement, updated kitchen appliances and countertops, luxury vinyl plank flooring, new doors, and more. Additional deck improvements are underway, including replacement of a portion with durable PVC decking to match the existing surface. The home also features whole-house water filtration and reverse osmosis drinking water systems. Located in Captain's Cove, residents enjoy indoor and outdoor pools, a golf course, marina, boat ramp, fitness center, restaurant, pickleball and basketball courts, playgrounds, walking trails, dog park, and more. Whether you're looking for a full-time residence or vacation retreat, this home offers a wonderful opportunity to enjoy the Eastern Shore lifestyle.

2353 Yardarm Dr, Greenbackville

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

2347 Mayflower Dr, Greenbackville
$276,000
3 Beds ⋅ 2 Baths
4/1993 Well maintained 3 bed/2 bath ranch-style home with an open floor plan. The living room features cathedral ceilings, a Quadra Fire cast iron wood burning stove, perfect for nights when you just want to cuddle up with a good book and reduces heating cost. Hardwood floors throughout Main Living Area, Dining Area and Hallway. Kitchen has a breakfast bar, gas stove, & dishwasher and a pantry closet with ample storage space. Primary bedroom has plenty of space with a large walk-in closet, bath with double bowl sinks and walk-in shower. Two additional bedrooms, second full bath and a laundry closet that is conveniently located in the hallway with a dryer on pedestal with drawer complete the layout of the home. Interior of home has been freshly painted. Step outside to the front concrete porch or a back deck with a ramp where you can enjoy the fresh air & peaceful setting. The attached one car garage provides additional storage space. Additional features: Generac Power System, concrete drive and a small shed and two open air firewood sheds to store firewood . Captains Cove Golf & Waterfront Community is the fastest growing Golf & Waterfront Community on the Eastern Shore of VA, Amenities offered: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball & Pickle-ball Courts, Playground, Picnic Area, Dog Park, Biking & Walking Trails, Security and more. Call for your private showing!

2347 Mayflower Dr, Greenbackville

Listing courtesy of Hall Realty. Contact:

3352 Scimitar Way, Greenbackville
$794,000
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:

5344 Sunrise Dr, Chincoteague Island
$829,500
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:

24227 Thicket Point Ln, Onancock
$1,799,000
8 Beds ⋅ 6 Baths
PRICE IMPROVEMENT! 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:

37323 Davey Jones Blvd, Greenbackville
$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:

3238 Amidship Dr, Greenbackville
$344,888
4 Beds ⋅ 3 Baths
Topaz "C" Model offered by Gemcraft Homes New Construction, MOVE-IN READY. Two-Story Single Family home featuring 4BR/2.5 BA, 1,911 sq ft., 2 Car garage. Main level offers an expansive open floor plan great room, kitchen and breakfast nook perfect for entertaining. Choice room on first level would make a great office space/reading room. Second level includes a large owners suite with walk-in closet, 3 additional BR's, hall bath and laundry area. Options available to add your own personal touch. Pictures may have upgraded features. Captains Cove Golf & Waterfront Community amenities offer: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball & Pickle Ball Courts, Playground, Walking & Biking Trails, Picnic Area, Dog Park, Security and such much more. Call today for your private showing. Captains Cove is located on Virginia's Eastern Shore and conveniently located close to major Metropolitan Areas along the East Coast. Within 3 Hours of Baltimore MD/Washington DC/Philadelphia PA, 5 hours from New York, 1 Hour from Ocean City MD, 2 hours from Virginia Beach/Norfolk/Hampton VA and only 20 minutes from the notorious Chincoteague Island VA.

3238 Amidship Dr, Greenbackville

Listing courtesy of Hall Realty. Contact:

4443 Shady Ln, Chincoteague Island
$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:

6498 Church St, Chincoteague Island
$395,000
2 Beds ⋅ 2 Baths
Practically brand new, this beautifully rebuilt rancher on Chincoteague Island offers the perfect blend of modern comfort and coastal charm—just moments from downtown and directly across the street from the beloved Church St Produce, famous for its homemade pies and local favorites. Inspections are available Rebuilt from the studs, this home features all-new roofing, windows, electrical, plumbing, and more—giving you the peace of mind of new construction with the character of an established setting. Situated on three lots, the property offers generous space, privacy, and plenty of parking with a large driveway and carport. Inside, enjoy true one-level living with a bright, open layout. The spacious living room welcomes you with a vaulted ceiling, exposed beams, a cozy fireplace (as is), and a beautifully finished wood planked ceiling that adds warmth and character to the space. Luxury vinyl plank flooring flows throughout the main living areas, while fresh carpet adds comfort to both bedrooms. The large eat-in kitchen provides ample space for gatherings and everyday living. This home features a convenient half bath, a dedicated laundry room for added efficiency, and a spacious full bath designed for comfort. Step outside to enjoy the covered front porch or unwind on the expansive rear deck overlooking the peaceful pond backdrop. A storage shed offers additional room for tools, beach gear, or hobbies. Located close to Chincoteague’s shops, dining, parks, and waterfront attractions, this home delivers the ideal island lifestyle—whether you're seeking a full-time residence, vacation retreat, or investment opportunity. Move-in ready and thoughtfully upgraded, this is a rare chance to own a like-new home in one of the island’s most convenient and charming locations.

6498 Church St, Chincoteague Island

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

4145 Hur Ln, Chincoteague Island
$334,500
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:

25323 Oceanview Ct, Accomac
$995,000
5 Beds ⋅ 5 Baths
Exquisite 5BR/4.5BA waterfront retreat in a gated community! 3,678 SF on 3.8 acres with sweeping ocean, marsh & creek views. Watch sunrises and rocket launches from screened porches and open decks with fireplaces. Private pier w/ boat lift and barrier island boat shuttle. Extended pier & floating dock. Large open floor plan with panoramic vistas. Theater, game room, multiple suites & garage for toys. New Appliances, Full home generator, Furnished & Turn-Key. High Speed Internet! Dues only $800/year. Enjoy the peacefulness of the setting of this well- appointed home. Even the Deer love it here! There is no need to leave when you reach this paradise. Elevator Shaft is built in... It's an absolute must see property!

25323 Oceanview Ct, Accomac

Listing courtesy of Beach Bay Realty. Contact:

5403 Pearl Dr, Chincoteague Island
$950,000
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:

8005 Hickman Farm Rd, Wallops Island
$780,000
3 Beds ⋅ 3 Baths
A rare opportunity to create your ideal equestrian or farm retreat on over 36 acres of scenic Wallops Island land, where open pasture views, privacy, and versatility come together. This under-construction barndominium is designed for those seeking space to live, work, and enjoy a true rural lifestyle—without sacrificing proximity to coastal amenities. The expansive ground level offers over 3,000 square feet of stable space with 18 stalls, along with a convenient half bath—ideal for daily barn use, livestock care, and equipment needs. A finished entry/mudroom provides a practical transition from barn to home before heading upstairs to the living quarters. The upper level features over 2,400 square feet of living space with 3 bedrooms and 2 full bathrooms. A spacious mudroom-style foyer with dual closets easily accommodates boots, gear, and daily essentials. The open-concept kitchen, dining, and living area creates a welcoming hub for everyday living and entertaining, with the living room opening to a large deck overlooking open pastureland bordered by a tree line, offering peaceful views and privacy. Two guest bedrooms share a generous full bath accented with shiplap walls and access to a shared deck, while the primary suite provides a private retreat with a walk-in closet and spacious en-suite bath. Luxury vinyl plank flooring and recessed lighting enhance the modern, comfortable feel throughout. The home is under construction, giving buyers the option to select and complete interior finishes with the seller or purchase the property as-is and finish it to their own vision. The barndominium structure features vertical metal siding and a metal roof, offering long-term ease of ownership. Conveniently located near Wallops Flight Facility, Assateague Island beaches, and the shops and dining of Chincoteague Island, this property offers an exceptional blend of acreage, flexibility, and lifestyle—perfect for equestrian enthusiasts, farmers, or anyone seeking space to create something truly special.

8005 Hickman Farm Rd, Wallops Island

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

18286 Woodland Ave, Parksley
$225,000
3 Beds ⋅ 1 Baths
Charming, inviting, and full of character, this beautifully renovated one-story home is tucked away on a large wooded lot along a quiet rural street in Parksley. From the moment you step inside, you’ll appreciate the extensive top-to-bottom renovation, freshly painted interiors, and thoughtful updates that complement the home’s original charm. Arched doorways and built-in bookcases in the living room add architectural interest and personality, creating warm and welcoming spaces throughout. The bright, sunny kitchen is a standout, offering an impressive amount of space. Crisp white finishes give the room a fresh, airy feel, while breakfast bar seating provides the perfect spot for casual meals or morning coffee. New LVP flooring, new stainless steel appliances, and plenty of room to cook, gather, and entertain make this kitchen both attractive and functional. Just off the living room, a ceramic-tiled sunroom offers wonderful flexibility and can easily serve as a third bedroom, guest room, home office, or relaxing retreat. Filled with natural light and overlooking the wooded surroundings, this versatile space adds valuable living options to the home. From the sunroom, step outside onto the deck overlooking the peaceful backyard , a lovely setting for outdoor dining, entertaining, or unwinding at the end of the day. The home features two generously sized bedrooms with neutral paint, including a spacious main bedroom with the added convenience of double walk-in closets. A full hall bath completes the living space. Additional features include an attached one-car garage for convenient parking and storage, recessed lighting, as well as a large detached outbuilding with electric—an ideal setup for a workshop, hobby space, studio, or additional storage. Set on a generous wooded lot, this move-in-ready property offers the peaceful feel of country living while being nestled along a quiet Parksley street. With its extensive renovations, flexible one-level layout, inviting indoor and outdoor spaces, and abundance of charm, this delightful property offers a wonderful combination of comfort, character, and peaceful Eastern Shore living.

18286 Woodland Ave, Parksley

Listing courtesy of Northrop Realty. Contact:

26355 Mount Nebo Rd, Onancock
$799,000
3 Beds ⋅ 2 Baths
106-acre estate that perfectly blends rural tranquility with waterfront luxury. This charming 3-bedroom, 2-bathroom home offers the best of both worlds with productive farmland mixed with mature timber, creating a landscape that's as beautiful as it is functional. Offering an impressive 1,700 feet of pristine water frontage, where morning coffee tastes better and evening sunsets paint the sky in colors that no artist could replicate. This waterfront access transforms everyday living into a vacation-like experience. Inside, you'll find a thoughtfully designed home, wood burning fireplace, and a screen porch. 900 feet of perennial streams with vegetated buffer,7acres of marsh, 48.7acres of prime ag soils, 49.65acres of forest land, within Chesapeake Bay preservation area.

26355 Mount Nebo Rd, Onancock

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

3375 Anchor Ct, Greenbackville
$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:

2497 Dry Dock Ct, Greenbackville
$404,888
3 Beds ⋅ 2 Baths
Sussex Model Elevation "C" w/2'side extensions offered by Gemcraft Homes New Construction, MOVE -IN READY. One of Gemcraft Homes newest and most popular house plan design.. The Sussex boasts single level living at its best! Featuring 3 bedrooms and 2 full baths, 1980 sq ft., 2 car garage. Home offers an open concept floor plan with an airy great room that adjoins the dining area and kitchen. Features include:granite countertops, 42" cabinets, Deluxe Kitchen Island, 9' Ceilings, SS Appliances & 60" Simplifire Allusion Slim Electric Fireplace located in the Great Room. The owner's suite includes an abundance of space with two walk-in closets and private bath. Pictures may have upgraded features. For a little relaxation a screen porch has been added to this home. Captains Cove Golf & Waterfront Community amenities offer: 9 Hole Pristine Golf Course, 3 Pools (2 Outdoor/1 Indoor), Fitness Center, Boat Ramp, Basketball & Pickle-ball Courts, Playground, Walking & Biking Trails, Security and more Call for your private showing today.

2497 Dry Dock Ct, Greenbackville

Listing courtesy of Hall Realty. Contact:

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