143 houses for sale in East Chop

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

WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilit

Easy Edgartown living awaits in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout that works beautifully for everyday life, entertaining, or relaxed seasonal stays. The private primary suite includes its own bath, while two additional bedrooms share a full bathroom, creating a practical and comfortable floor plan. A full basement provides excellent storage and added flexibility, with room for bikes, beach gear, tools, or future possibilities. Step outside to enjoy the deck, fenced yard, and quintessential outdoor shower - the perfect Vineyard touch after a day at the beach. With the bus stop conveniently located at the end of the street, getting around the island is simple and stress-free. Just minutes from downtown Edgartown, bike paths, restaurants, shops, and some of the island's most loved bea

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,

Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown's historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana-an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location

27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with seating for four. The kitchen sports Bosch appliances, an island with a built in drawer microwave, quartz countertops and an easy layout for cooking and entertaining. The kitchen then opens to a separate dining room. A half bath off the living room and a first floor primary bedroom with a luxurious private bath completes the first floor. The second floor offers a second living room and two guest bedrooms, each with their own bath. The plot is large enough to support a future pool, and a detached garage. Come and enjoy! The pictures are of a similar home that was built

Set within the historic fabric of Edgartown Village, 14 Thayer Street is a property of uncommon scale and quiet distinction. Occupying a 0.62-acre parcel, rare for this in-town setting, the grounds offer a sense of space and privacy just moments from the harbor and village center. The residence is attributed to Frederick Baylies Jr the builder of the Whaling Church, and reflects the enduring architectural traditions that define Edgartown. With five bedrooms and five baths across more than 3,100 square feet, the home is both comfortable and unpretentious, suited to long summer stays and informal gatherings. Mature landscaping and open lawn frame the house, lending a sense of seclusion that is increasingly difficult to find within the village. Properties of this scale and provenance seldom come to market, offering a measured opportunity to steward a piece of Edgartown's architectural legacy

This year-round home, situated less than half a mile from Lambert's Cove Beach, boasts fine craftsmanship and character in a peaceful, wooded environment. Inside, the open living room features wide plank floors, cathedral ceilings with beams, and a central brick fireplace that connects seamlessly to the updated kitchen

Fantastic location near Falmouth Heights Beach, Falmouth Harbor, Island Queen, Main Street restaurants and shopping. 3 bedrooms and 2 full baths. Living room, family room, kitchen with dining area. Full bath on both first and second floor. Roof 2022. Hot water tank 2024. Freshly painted interior. This location is ideal for ease of getting on and off the Cape and then enjoying all the things that make Falmouth such a special Cape Cod town

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows seamlessly throughout the home. Offering 10 well-appointed rooms, the residence features six bedrooms, four full bathrooms, and two powder rooms. The gourmet kitchen opens to the spacious living and dining areas, creating an inviting gathering space that extends through French doors to a generous bluestone patio. The beautifully landscaped yard is highlighted by a private, thoughtfully sited swimming pool, providing a peaceful outdoor retreat perfect for relaxing or entertaining

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

ENJOY THE SEA BREEZES AND SPECTACULAR VIEWS. Wake up to the ever-changing beauty of Vineyard Sound, watch the ferries cross in the distance toward Woods Hole, and end the day with sunset views stretching down the Lagoon. Designed to celebrate its extraordinary setting, this 4-bedroom, 2.5-bath home offers a rare lifestyle defined by light, water, and effortless indoor-outdoor living. With commanding views from nearly every room, the home invites you to slow down and take in the scenery from every angle. Two levels of covered decks overlook Vineyard Sound, while two additional levels of decks face the Lagoon, creating multiple outdoor spaces for morning coffee, afternoon reading, summer entertaining, or quiet evenings under the stars. The first level offers three comfortable bedrooms, a spacious family room, a full bath with laundry, and generous storage - ideal for hosting family and friends after a day at the beach, on the boat, or exploring the Island. Upstairs, the sun-filled open l

Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown's historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house with full kitchen, and a two-car carriage house with additional living quarters. The property features a private backyard oasis with a 16' x 32' saltwater pool, spa, and pool cabana-an exceptional outdoor setting in Edgartown Village. With furnishings and window treatments included, the home is ready for immediate enjoyment. 114 North Water Street represents a turnkey Edgartown Village estate offering the scale, amenities, and setting that are seldom available in this iconic location

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

Nestled in the sought-after seaside neighborhood of Menauhant, this fully renovated Cape Cod-style home blends classic coastal charm with modern comfort. Set on half an acre, the property offers privacy while being just a short walk down a path to the sandy shores of Menauhant Beach. The home features 4 bedrooms and 4.5 bathrooms, including three en-suite bedrooms for added comfort and privacy. Enjoy ocean and marsh views from the living room, kitchen, and dining area-perfect for entertaining or relaxing after a day at the beach. Thoughtful renovations and high-end finishes enhance the home's elegant yet relaxed coastal feel. Enjoy the spacious yard for outdoor gatherings or quiet evenings in the sea breeze. Ideally located just a scenic coastal drive to the restaurants, shops, and nightlife of Main Street in Falmouth, this home offers the perfect balance of tranquility and convenience-ideal as a year-round residence or Cape Cod getaway. Listing Agent is related to Seller

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

Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle

The Pinkletink Could be Yours! This unspoiled 1950's cottage is named for the Island's tiny frogs who sing the announcement of spring. The location is sublime, just 5 blocks from Inkwell Beach and only a few more to the top of Circuit Avenue, while feeling miles away in this quiet location near Farm Pond. Cherished by its owners for decades, the cottage has been lovingly maintained while keeping its authentic island charm intact

WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilit

Falmouth heights rare find! Total renovation; must see. With views of Falmouth Harbor, it's not just a home, but a front-row seat to all that Falmouth has to offer. Walk from your front door to beaches, restaurants, Falmouth Harbor, shopping, or a stroll to the Island Queen for a day at the Vineyard. This beautiful, totally renovated dream home offers high-end modern amenities that pair perfectly with classic seaside charm. A complete transformation with extraordinary detail and finish work. Grand fireplaced family room w/ 7' oak floors which opens to an ultra-high-end kitchen with a spacious dining area and a slider to a fenced yard. Second-floor cathedral primary retreat with sumptuous bath, waterfall shower, and deck offering harbor views—two additional bedrooms with ultra bath & second-floor deck access. Head over to the kite field for 4th of July fireworks; the Falmouth Road Race steps from your door. This is a Cape Cod experience that most people dream of, and few experience!

3 houses from the beach can be your new getaway! Enjoy relaxing views from your 2 bedroom Cape Cod cottage and a separate 1 bedroom 1 bath building for guests or family. The time has come to make way for new memories and fun! Feel the sand in your toes and smell the ocean breezes. This property is NOT on sewer. 2014 Septic installation. Documents Attached to Listing or available

Less than 0.5 mile to Falmouth Heights Beach—this is the kind of Falmouth Heights location that rarely becomes available and doesn’t last. Sidewalk-lined streets lead to the shoreline, with Falmouth Harbor, the Island Queen ferry, and Main Street just 1.5 miles away. Beach days, boat rides, dinner out, and morning coffee—everything that defines summer on Cape Cod is right here, without compromise. Set on a. 24-acre lot, this 3-bedroom, 1.5-bath Cape offers. 1,404 sq ft with a flexible layout, including a main-level bedroom and bath that adds everyday convenience. Beautifully maintained with timeless charm, the home offers immediate comfort along with opportunity for future customization. Out back, the fenced yard is designed for summer living with an outdoor shower, retractable awning for shade, and a firepit area perfect for easy evenings after the beach. A proven coastal location with strong rental appeal, immediate enjoyment, and long-term upside—opportunities like this don’t wait

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!

3 bedroom house + 1 bedroom apartment! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 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 your mortgage. The main house features a stunning solarium or sunroom, a cheerful efficient kitchen, and a sweet living room anchored by a beautiful stone fireplace. The main house has been emptied out 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, radiating a clean and bright atmosphere. Situated on a spacious lot, the site is large enough to support a 4-bedroom septic system; a design is currently being finalized by Sourati Engineering (buyer to be financially responsible for the upgrade). Other features include oak floors, two decks for outdoor enjoyment, a vintage ga

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