358 houses for sale in Vineyard Highlands

Stylish, thoughtfully designed ranch style home built in 2014 is bright and sunny. Tucked away in a private tranquil setting just a stroll to downtown, harbor, beaches, ferries, library, restaurants and shops, the home features solar panels, large living room with separate dining area, kitchen with stainless steel appliances, 3 bedrooms, 2 full baths with tiled floors, and laundry room. Completing the home is a large rear deck, irrigation system, and a walkout basement that would make a great bonus room, family room or home office. Parking in driveway, plus second parking area off cul-de-sac. Perfect for year-round or summer vacation/rental home

RECENTLY COMPLETED and in a league of its own in Falmouth Heights. Nothing to renovate. Nothing to compromise. Everything to love about this exceptional water-view home, just steps from Falmouth Harbor and Falmouth Heights Beach. Pristine and thoughtfully renovated, this three-bedroom, two-and-a-half-bath residence blends timeless Cape Cod character with exceptional craftsmanship and sophisticated finishes. Wide-plank, 6.5-inch French oak hardwood flooring flows throughout, while the beautifully designed kitchen features leathered quartz countertops, a custom farmhouse sink, and custom cabinetry with convenient pull-out shelving. The buyer will also have the opportunity to select the LG refrigerator configuration that best suits their preferences. After a day at the beach, rinse off in the inviting outdoor shower, gather around the gas fireplace, or unwind during a relaxed summer evening in one of Falmouth Heights' most desirable neighborhoods. Additional amenities include oil heat, ai

424 and 426 Grand Ave are 2 separately deeded homes with beautiful views of Falmouth Harbor and Vineyard Sound being sold as a package or individually. They share a driveway and a deck. They each have 2 beds, 1 bath on their main levels and each have 1 bed 1 bath in their walk out lower levels. This is an amazing opportunity for family, friends, or investors to buy a property in an area that rarely comes up for sale. All info is combined and property specific numbers are available at request. Enjoy fireworks, road race, restaurants, ferry service to Martha's Vineyard, farmers markets, concerts, etc from this legacy location. Step inside this beautifully maintained property and unplug. Experience a real Cape Cod lifestyle this Summer!

LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES. Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history. Set on an oversized lot just two parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous accommodations for family, friends, and guests. From the EXPANSIVE ROOFTOP entertainment deck, enjoy sweeping 180-degree water views of Vineyard Haven Harbor - a spectacular vantage point for watching ferries and sailboats glide by at sunset. Originally built in 1859 by noted whaling captain Shaw Norris, this classic Greek Revival residence seamlessly blends historic character with modern luxury. Extensive renovations - including a new roof, siding, trim, and all-new mechanical systems - have transformed the property into a home that lives like new construction while preserving its architectural i

Waterfront Estate with Deep-Water Dock and Private Beach. Experience an exceptional Martha's Vineyard waterfront lifestyle at this rare Lagoon Pond offering, ideally located just minutes from Vineyard Haven's vibrant harbor, restaurants and shops. The property features a private deep-water dock-ideal for the avid boater-along with its own sandy beach for effortless access to the water. The refined residence was completely renovated in 2022, with interiors by Nicole Hogarty Designs. Filled with natural light and expansive water views, the home is complemented by beautifully landscaped grounds and mature specimen trees, creating a private setting for outdoor living and entertaining. Amenities include a professional-grade bocce court, cold plunge, large hot tub, and classic Island outdoor shower. A separate, stylish party barn provides a versatile setting for everything from intimate gatherings to summer celebrations. Offering an uncommon combination of privacy, waterfront access, boating

Located in Oak Bluffs' desirable East Chop neighborhood, this 10,000+/- sq. ft. R2-zoned property offers an exceptional opportunity to renovate or build new (subject to applicable approvals). The existing two-bedroom, one-bath home is being sold as is. The level lot features a spacious yard and is ideally located just 0.9 miles from the East Chop Lighthouse, 1.3 miles from the East Chop Beach Club, and only minutes from downtown Oak Bluffs, the harbor, beaches, ferries, restaurants, and shops. The property is currently served by a failed cesspool and will require installation of a Title 5-compliant septic system. Buyers are encouraged to perform their own due diligence regarding zoning, permitting, redevelopment potential, and septic requirements

Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking. 33 Lagoon Pond Road is a newly constructed, thoughtfully designed three bedroom, three bathroom home where luxury meets sophisticated coastal charm. Featuring an open floor plan, a designer kitchen with quartz countertops, custom tile bathrooms, and seamless indoor-outdoor living, the home enjoys water views from the living room, bedrooms, and inviting front porch. A private backyard, spacious rear deck, and attached two car garage provide both privacy and convenience, while the property's impressive rental history adds outstanding investment appeal. Complementing the main residence is 29 Lagoo

Located in Falmouth Heights, less than two-tenths of a mile from Falmouth Heights Beach, this well-built three-bedroom home offers an exceptional opportunity in one of Falmouth's most desirable seaside neighborhoods. Set on a generous corner lot outside the flood zone, the property offers added space and privacy while remaining close to the beach, Falmouth Harbor, and downtown Falmouth. Built in 1983, the home offers the advantages of more modern construction, including a poured concrete foundation and full basement. The flexible floor plan features two bedrooms on the first floor and a third bedroom upstairs. Recent improvements include a newer roof and fresh interior paint throughout, creating a clean canvas for new owners to make it their own. The spacious yard offers room for outdoor living, gardening, and recreation. Enjoy easy access to seaside dining, the Heights ballfield, and the summer traditions that make Falmouth Heights so special. Whether it's a morning walk to the beach,

Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and entertaining. The kitchen overlooks the dining area, an intimate sitting area, and a versatile game and reading area beyond. The spacious TV and family room features custom built-in bookcases and French doors that open onto a bluestone patio and the pool area beyond. A generous screened porch provides additional living space. Completing the first floor is a large guest bedroom with an ensuite bath, along with a powder room, pantry, mudroom, and laundry room. Upstairs, the gracious primary suite features vaulted ceilings, a sitting area, and a luxurious bath with a soaking tub. There are two additional gu

Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming two-bedroom oceanfront cottage on East Chop. Set on approximately.21 acres of waterfront property with more than 50 feet of shoreline, this special retreat offers a rare opportunity to own a true piece of the island's coastline. Positioned directly on the water, the cottage captures the beauty of the ever-changing ocean from sunrise through sunset. Inside, the cozy two-bedroom cottage offers an inviting island escape with an intimate connection to its spectacular surroundings. Step outside and experience the salt air, gentle sea breezes, and the unmistakable magic of waterfront living. Whether you're enjoying your morning coffee while watching the boats pass, gathering with family and friends, or simply listening to the waves from your own waterfront property, this is a place designed to create lasting Martha's Vineyard memories. A rare East Chop opportunity-over 50 feet of oceanfront.21 acres of wa

Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitchen. The first floor features a primary bedroom, a full bath with laundry, and a separate mudroom/back entry. Recent updates include a new kitchen with new appliances, new baths, fresh interior and exterior paint, new lighting, and new flooring and carpet throughout

Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable lot. For 35 years, home of Susan Branch, the illustrious self-taught illustrator and author of New York Times best-seller Martha's Vineyard, Isle of Dreams, this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,468 s.f. of indoor space including the summer kitchen (now pantry/laundry) on more than a half acre in town with wood floors throughout and cheerful eastern sunlight mornings and western afternoon sunlight with evening skies. With period paneling, crown molding, and 9' ceilings, the floor plan includes front hall entry with lovely curved staircase, front parlor-studi

Historic Water View Elegance Meets Modern Luxury in Vineyard Haven: Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary living. There are 5 total bedrooms, 2 on the first floor and 3 on the second floor. There are 2 en suite bedrooms, 1 on the first floor and 1 on the second floor. In addition, there are 4 full bathrooms (3 newly renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central air conditioning, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining and summer barbecues. And a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly po

Directly across from the iconic Heights Beach, sits this beautifully appointed Cape style residence offering the quintessential Falmouth coastal lifestyle. Perfectly positioned to capture sparkling water views and cooling ocean breezes, the home enjoys a front-row seat to one of Cape Cod's most beloved beaches, known for its expansive sandy shoreline, Vineyard Sound vistas, and vibrant summer atmosphere. Inside, sun-filled living spaces are designed for comfort and gathering, while classic architectural details create a timeless coastal retreat. Expansive windows frame water views, and the inviting ocean view porch is the perfect place to enjoy morning coffee, afternoon sea breezes, or spectacular evening sunsets. Just moments from Falmouth Village, the Island Queen ferry to Martha's Vineyard, restaurants, shops, and the finish line of the renowned Falmouth Road Race, this exceptional property places the very best of Cape Cod at your doorstep. Enjoy the celebrated 4th of July fireworks

Welcome to your Vineyard dream home in the highly sought-after West Chop neighborhood. This exceptional brand-new construction offers 6 bedrooms, 6 full baths, and 1 half bath, thoughtfully designed with timeless coastal elegance and modern luxury. Filled with natural light, the home's bright and airy interior showcases impeccable craftsmanship, spacious living areas, and a gourmet chef's kitchen featuring premium high-end appliances, custom cabinetry, and an oversized island perfect for entertaining. An inviting home office provides a quiet space to work remotely, while the expansive bonus room with a wet bar offers the ideal setting for gatherings, game nights, or relaxing with family and friends. Designed for seamless indoor-outdoor living, a sun deck overlooks the stunning pool and beautifully landscaped grounds, creating a private retreat for summer enjoyment. The property is set on just under an acre and framed by mature trees, offering both privacy and tranquility. From select v

Rare downtown Vineyard Haven compound offering! A unique opportunity to own two separate properties offered together just moments from the ferry, harbor, restaurants, and shops. 33 Lagoon Pond Road is a newly built 3BR/3BA home featuring an open floor plan, designer kitchen with quartz countertops, custom tile baths, water views, private backyard, spacious deck, attached two-car garage, and strong rental history. Complementing 33 Lagoon Pond Road, is 29 Lagoon Pond Road originally built in 1950 and beautifully renovated in 2020. This 2BR/1BA cottage with a private patio and outdoor shower, is ideal for guests, extended family, employee housing, or additional rental income. A rare highlight is the oversized rear parking lot accommodating approximately 10 vehicles-an exceptional amenity in downtown Vineyard Haven. Whether you're seeking a family compound, investment property, or luxury in-town retreat with unmatched flexibility and income potential, this one-of-a-kind offering is not to

Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just.3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations. Home is being sold 'as is'. Septic is a functioning cesspool but it will need to be upgraded. Basic engineering is being completed and a septic plan is being drawn up. It will be the Buyer's responsibility to have the plan approved and complete the installation as part of the overall

Location, location, location: This 1999 home with all the comforts of the 21st Century is nestled on a landscaped lot within mellow surroundings. And yet. it's located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation hardly gets better. The 3BR/2.5BA house features a deep wraparound farmer's porch, Brazilian cherry floors, an open and flexible layout, recent kitchen and bath updates, a generous 2nd floor bonus room and an attached single-car garage. The poured basement stands ready for your finishing whims. Kick back in your sunny backyard or on your shady porch with the distant peek of Nantucket Sound. Songbirds will serenade you from towering maples and oaks. Pinkletinks will chime in from Farm Pond. It's no wonder that this abode has been loved - by vacation tenants as well as the owner. Note: This property lies within the jurisdiction of the Cottage City Historic District and Copeland District of the Town of

'The Doll House' is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering swimming, kayaking, and paddleboarding from your backyard. The main house features a welcoming sun porch, living room with a stone fireplace, light-filled primary bedroom with water views, and an updated kitchen and dining area with brick floors and a built-in window seat. French doors open to a spacious lawn and a charming former boathouse converted into a unique dining pavilion. Additional highlights include a rooftop deck with panoramic water views, guest cottage, outdoor shower, garage with office, and garden shed. A quintessential Martha's Vineyard waterfront esc

Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back deck. The second floor has a huge front-to-back primary bedroom, a large landing, full bathroom and two guest bedrooms. Although the property is in need of updates, it will be well worth the effort. There is a ton of potential here. Being offer as is

Live the quintessential Cape Cod life in this meticulously maintained cottage or make all the changes you want as this location supports any upgrades. Views from every window, access to all the activities Falmouth Heights and Falmouth Harbor have to offer. Year round, seasonal, owner occupied or investment. your options are endless. Purchase this property separately or buy it with 424 Grand Ave as a package

Three houses from the beach. Two cottages. Endless Cape Cod memories waiting to happen. This distinctive property offers a 2-bedroom, 1-bath main cottage plus a separate seasonal 1-bedroom, 1-bath cottage—an incredibly versatile setup for family, friends, and summertime guests. Imagine waking up to the coastal breeze, walking to the beach in minutes, spending the afternoon in the sand, and ending the day relaxing at your own Cape Cod retreat. The separate cottage gives everyone a little more space while preserving the easygoing charm that makes summers in Falmouth so special. Whether you're searching for your own weekend escape or a place where family traditions can continue for years to come, the combination of location and two separate buildings makes this property a rare find. The beach is practically your backyard—now it's time to make it yours. Property is not on sewer. Septic system installed in 2014. Documents attached to listing or available. Photo renderings have been digitall

Recently completed & in a league of its own! Falmouth Heights water-view living, just steps from Falmouth Harbor and Falmouth Heights Beach. Pristine and thoughtfully renovated, this three-bedroom, two-and-a-half-bath home pairs timeless Cape Cod character with exceptional craftsmanship and high-end finishes. Wide-plank, 6.5-inch French oak hardwood flooring flows throughout, while the beautifully appointed kitchen features leathered quartz countertops, a custom farmhouse sink, custom cabinetry with convenient pull-out shelving, and the rare opportunity for the buyer to select the LG refrigerator that best suits their style. Gather around the gas fireplace after a day at the beach, or settle in for an effortless summer evening in one of Falmouth Heights’ most desirable neighborhoods. Additional features include first-floor oil heat, second-floor hydro-air heating, mini-split comfort, underground irrigation. Best of all, you can park the car and embrace the neighborhood on foot. Stroll

Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom tile bathrooms and seamless living both indoors and out. Enjoy water views from the living room, bedrooms and the inviting front porch, perfect for relaxing or entertaining, while the private backyard and spacious back deck provide the privacy many desire. The two-car garage provides a rare in-town convenience, for both parking and storage of your island car and beach gear. The property also boasts impressive rental history, look no further for your next in town purchase. An exceptional, well-rounded offering!

House & Apartment Near Lagoon! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This clean, bright, move-in-ready property features a 3 BR, 1 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset the mortgage. The main house, featuring a wonderful sunroom, an efficient kitchen, and a comfortable living room anchored by a beautiful stone fireplace, has been emptied and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout. Situated on a spacious corner lot, and located a short distance to down town and public Lagoon access, this property is a super value. Seller will credit the buyer the cost of a brand new septic system at closing

Recently completed & in a league of its own! Falmouth Heights water-view living, just steps from Falmouth Harbor and Falmouth Heights Beach. Pristine and thoughtfully renovated, this three-bedroom, two-and-a-half-bath home pairs timeless Cape Cod character with exceptional craftsmanship and high-end finishes. Wide-plank, 6.5-inch French oak hardwood flooring flows throughout, while the beautifully appointed kitchen features leathered quartz countertops, a custom farmhouse sink, custom cabinetry with convenient pull-out shelving, and the rare opportunity for the buyer to select the LG refrigerator that best suits their style. Gather around the gas fireplace after a day at the beach, or settle in for an effortless summer evening in one of Falmouth Heights’ most desirable neighborhoods. Additional features include first-floor oil heat, second-floor hydro-air heating, mini-split comfort, underground irrigation. Best of all, you can park the car and embrace the neighborhood on foot. Stroll

Spectacular water views from nearly every room! Breathtaking sunrises and sunsets overlooking Vineyard Sound, Bristol and Falmouth Heights Beaches, and Little Pond. This home offers one of the finest vantage points in town for enjoying the Fourth of July fireworks. Offered for the first time in over 100 years, this exceptional property combines timeless character with comfortable living. Rebuilt in 1992, two properties were combined and the structure was raised 14 ft. Providing for a garage and basement. The convenience of one floor living is provided with an elevator, first-floor bedroom suite, and first floor laundry. Multiple living spaces are provided for entertaining family and friends. The sun-filled sunroom is the perfect place to start your morning. Additional features include a two-car garage, wrap-around deck, and a private yard ideal for summer enjoyment. Mechanicals on first and second floors. New 2000-gallon septic tank installed in 2026. Passing Title V in hand

Rarely does an opportunity like this come along - two cottages just three houses from the beach! Relax and take in the coastal surroundings, feel the ocean breezes, and enjoy the extraordinary convenience of having the beach just steps from your door. Set in one of the most sought-after settings for enjoying the Falmouth coastal lifestyle, this property includes a 2-bedroom, 1-bath Cape Cod cottage and a separate seasonal 1-bedroom, 1-bath cottage. The second cottage adds an exceptional layer of flexibility for family and friends, guests, or simply creating a private summer retreat. Whether your dream is a classic Cape Cod getaway, a place for generations to gather, or a special property near the water, this offering deserves a close look. The time has come for new owners to create their own Cape Cod memories. Property is not on sewer. Septic system installed in 2014. Documents attached to listing or available

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage. Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water beyond. The interior feels open, calm, and intentional, with spaces that flow naturally toward the outdoors and keep the focus where it belongs. Outside, the landscape opens gently toward the water. A private beach path sits immediately adjacent to the Vineyard Haven Yacht Club, offering sailing, tennis, dock access, and a cafe just steps away, an uncommon amenity pairing in such a peaceful, natural setting. Whether enjoyed as a personal escape or leveraged as an income-producing property, the home's strong rental history reflects its wide appeal. A rare opportunity to own directly on Vineyard Have