358 houses for sale in Vineyard Highlands

East Chop with Water View! The perfect size vacation house or year round living, with all the bells and whistles, water views and located in the most desired neighborhood on East Chop! Designed by Hutker Architects, built with high quality craftsmanship by J.G. Early and landscape design by Dan Gordon Landscape Architects. This recently completed cozy 2BR/2.5 BA with solar panels providing remarkable results in energy efficiency and cost savings, includes an electric car charging station in the garage with the option to move to either side, landscaped yard and is conveniently located near the East Chop beach club, tennis courts and yacht club, downtown, the harbor, ferries, restaurants and shops. With construction completed in 2024 the property is virtually new. This comfortable year-round home includes an open floor plan with living room, a propane log fireplace, kitchen with countertop seating, a classic dining booth, a mudroom with washer and dryer, and powder room on the 1st floor.

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet. The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis. The lower level consists of a finished bonus room, laundry, and a fu

Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired decor throughout, and comfortable spaces designed for relaxed Vineyard living and entertaining. A first-floor bedroom provides added flexibility, while the enclosed 120-square-foot sun porch creates a wonderful extension of the living space. Outdoor living shines with a newer mahogany outdoor shower, bluestone patio and beautifully designed walkway, all surrounded by a private setting. An unfinished basement provides approximately 720 square feet of additional space for storage and future possibilities. Walk or bike to Jetty Beach and the East Chop Lighthouse, enjoy the nearby East Chop Beach Club, or stroll to Oak Bluffs Harbor, downtown restaurants and shops. With a proven rental history and a desirable East Ch

Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home's original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs

This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor includes a private guest bedroom with its own bath, while the second floor offers two additional guest bedrooms and a generous primary suite with access to a large deck. These rooms share two well-appointed bathrooms. With dual road access, thoughtfully landscaped grounds, and a versatile garage space, this home provides both comfort and flexibility in a prime location

Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home's original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet. The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis. The lower level consists of a finished bonus room, laundry, and a fu

East Chop with Water View! The perfect size vacation house or year round living, with all the bells and whistles, water views and located in the most desired neighborhood on East Chop! Designed by Hutker Architects, built with high quality craftsmanship by J.G. Early and landscape design by Dan Gordon Landscape Architects. This recently completed cozy 2BR/2.5 BA with solar panels providing remarkable results in energy efficiency and cost savings, includes an electric car charging station in the garage with the option to move to either side, landscaped yard and is conveniently located near the East Chop beach club, tennis courts and yacht club, downtown, the harbor, ferries, restaurants and shops. With construction completed in 2024 the property is virtually new. This comfortable year-round home includes an open floor plan with living room, a propane log fireplace, kitchen with countertop seating, a classic dining booth, a mudroom with washer and dryer, and powder room on the 1st floor.

Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home's original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs

This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor includes a private guest bedroom with its own bath, while the second floor offers two additional guest bedrooms and a generous primary suite with access to a large deck. These rooms share two well-appointed bathrooms. With dual road access, thoughtfully landscaped grounds, and a versatile garage space, this home provides both comfort and flexibility in a prime location

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet. The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis. The lower level consists of a finished bonus room, laundry, and a fu

Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired decor throughout, and comfortable spaces designed for relaxed Vineyard living and entertaining. A first-floor bedroom provides added flexibility, while the enclosed 120-square-foot sun porch creates a wonderful extension of the living space. Outdoor living shines with a newer mahogany outdoor shower, bluestone patio and beautifully designed walkway, all surrounded by a private setting. An unfinished basement provides approximately 720 square feet of additional space for storage and future possibilities. Walk or bike to Jetty Beach and the East Chop Lighthouse, enjoy the nearby East Chop Beach Club, or stroll to Oak Bluffs Harbor, downtown restaurants and shops. With a proven rental history and a desirable East Ch

East Chop with Water View! The perfect size vacation house or year round living, with all the bells and whistles, water views and located in the most desired neighborhood on East Chop! Designed by Hutker Architects, built with high quality craftsmanship by J.G. Early and landscape design by Dan Gordon Landscape Architects. This recently completed cozy 2BR/2.5 BA with solar panels providing remarkable results in energy efficiency and cost savings, includes an electric car charging station in the garage with the option to move to either side, landscaped yard and is conveniently located near the East Chop beach club, tennis courts and yacht club, downtown, the harbor, ferries, restaurants and shops. With construction completed in 2024 the property is virtually new. This comfortable year-round home includes an open floor plan with living room, a propane log fireplace, kitchen with countertop seating, a classic dining booth, a mudroom with washer and dryer, and powder room on the 1st floor.

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

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Here is your opportunity to own a charming Cape close to beaches, the bike path and plenty of dining and shopping options. This home features wide plank wood floors on the first level and a full unfinished basement for storage and potential additional living space. Second level has two spacious bedrooms with cathedral ceilings and ample natural light. Rooftop widow's walk provides panoramic views. 3 bedroom septic has passed Title 5 inspection. This home is being offered as-is

An extraordinary opportunity to own one of the Cape's most distinctive waterfront properties, this exceptional 5.3-acre estate parcel combines remarkable natural beauty, complete privacy, and an unparalleled coastal setting. At its heart is a beautifully renovated four-bedroom beach cottage, thoughtfully updated with modern amenities while preserving the character and intimacy of a classic seaside retreat. From virtually every room, expansive water views create a seamless connection to the surrounding landscape. The property's exceptional topography and scale are among its defining features. A meandering private path descends naturally through the expansive grounds, leading to approximately 450 feet of private sandy beachfront, an extraordinary stretch of shoreline offering a rare sense of seclusion and direct access to the water. Set within a conservation-minded private enclave, the property enjoys an atmosphere of discretion and exclusivity. Its distinguished setting is further enhan

Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous.35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend of privacy, convenience, and classic island living. The comfortable single-level layout features three bedrooms and one-and-a-half baths, offering plenty of space for family, guests, or a relaxing Martha's Vineyard getaway. Step outside onto the sunny deck, an ideal spot for morning coffee, outdoor dining, or unwinding after a day at the beach. The lovely, spacious yard provides plenty of room for outdoor enjoyment, while the storage shed is perfect for beach equipment, bicycles, gardening tools, and seasonal belongings. Set on a quiet cul-de-sac with a desirable.35-acre lot, this home combines the tranquility of a residential setting with the convenience of being close to Oak Bluffs beaches

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

Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property. Located just 0.8 miles from downtown Oak Bluffs, the home offers convenient access to beaches, restaurants, shops, ferries, and the harbor, while enjoying the privacy of a quiet residential neighborhood. Over the past decade, the property has benefited from extensive improvements, including a four-bedroom septic system, energy-efficient mini-split heating and air conditioning, updated windows, renovated bathrooms, irrigation, an outdoor shower, and countless additional upgrades that reflect exceptional pride of ownership. Fully booked for the 2026 summer season, the property provides immediate rental income from day one while offering exceptional flexibility for future personal use or continued investment. The property is

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. 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!

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

Tucked away in a private, beautifully landscaped setting, this charming Vineyard farmhouse offers a wonderful blend of privacy, space, and in-town convenience. Just moments from town, the ferry, and shopping, the four-bedroom, three-bath home sits on a spacious 30,000-square-foot lot with a five-bedroom septic system. Inside, sun-filled spaces, warm wood floors, built-ins, and a welcoming layout create an easy, comfortable feel. The first floor includes a private bedroom with en suite bath, while upstairs offers three additional bedrooms, two full baths, and laundry. The spacious living room opens to an enormous screened porch and back deck overlooking the beautifully landscaped yard-perfect for morning coffee, summer gatherings, and long Vineyard evenings. A truly special place to make lasting memories

Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living space plus 700+ square feet of newly finished recreation space above the two-car garage, with a private entrance and second-floor deck. The inviting first floor features a spacious kitchen with center island and abundant counter space, an adjacent dining room with wood stove, and glass doors opening to a wood deck and bluestone patio. Multiple sitting areas, a living room with gas fireplace, and private office provide flexible spaces for relaxing and working. Upstairs, two guest bedrooms share an updated bath, while the spacious primary suite features a walk-in closet and light-filled bath with soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bath add comfort. Additional amenities include a two-car garage and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this versatile home offers an ideal setting for relaxed island

Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a patio overlooking the water. The kitchen with casual dining area connects to a screened porch, creating easy indoor-outdoor living. A heated Gunite pool and expansive yard enhance the tranquil setting. Additional features include a first floor bedroom, detached garage, full basement, and a newly installed Title V septic system designed for SIX bedrooms

This cared for contemporary is located in a mature neighborhood abutting Sheriff's Meadow. It has a three bedroom, one bath reverse floor-plan design that captures ample natural light from a serene park-like setting. Hardwoods and ceramic tile flooring, A/C mini-split heat-pumps, a rear balcony deck, outdoor shower, and a delightful terraced patio compliment this new opportunity. *Seller is offering a closing credit of up to $50,000.00 toward the required nitrogen septic system upgrade

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

Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property. Located just 0.8 miles from downtown Oak Bluffs, the home offers convenient access to beaches, restaurants, shops, ferries, and the harbor, while enjoying the privacy of a quiet residential neighborhood. Over the past decade, the property has benefited from extensive improvements, including a four-bedroom septic system, energy-efficient mini-split heating and air conditioning, updated windows, renovated bathrooms, irrigation, an outdoor shower, and countless additional upgrades that reflect exceptional pride of ownership. Fully booked for the 2026 summer season, the property provides immediate rental income from day one while offering exceptional flexibility for future personal use or continued investment. The property is

Two complete homes on one acre in Edgartown's Smith Hollow neighborhood - a rare find. Set at the end of a paved cul-de-sac, the property gives each house its own septic system, its own landscaped yard, and enough separation for real privacy.The main house has four bedrooms and two baths, along with a basement and a drive-under garage. The guest house features three bedrooms, two baths, a full basement, and laundry. With a solid rental history already in place, this is a chance to get two houses for the price of one

Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a patio overlooking the water. The kitchen with casual dining area connects to a screened porch, creating easy indoor-outdoor living. A heated Gunite pool and expansive yard enhance the tranquil setting. Additional features include a first floor bedroom, detached garage, full basement, and a newly installed Title V septic system designed for SIX bedrooms