371 houses for sale in East Chop

Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system

Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system

Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with a fireplace, a sun-filled sunroom, and a wraparound covered porch designed to take in the spectacular surroundings. The main house offers five bedrooms and three-and-a-half baths, while a detached two-car garage includes a private one-bedroom apartment above, ideal for guests or extended family. Nearly every room captures sweeping views of Vineyard Sound, where passing boats, ever-changing seascapes, and unforgettable sunsets create a remarkable backdrop. The beautifully landscaped grounds feature expansive lawns stretching to the edge of the bluffs, providing both privacy and dramatic scenery. Completing this rare offering are private steps to the shoreline, a deep-water pier, and a privat

'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

Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with a fireplace, a sun-filled sunroom, and a wraparound covered porch designed to take in the spectacular surroundings. The main house offers five bedrooms and three-and-a-half baths, while a detached two-car garage includes a private one-bedroom apartment above, ideal for guests or extended family. Nearly every room captures sweeping views of Vineyard Sound, where passing boats, ever-changing seascapes, and unforgettable sunsets create a remarkable backdrop. The beautifully landscaped grounds feature expansive lawns stretching to the edge of the bluffs, providing both privacy and dramatic scenery. Completing this rare offering are private steps to the shoreline, a deep-water pier, and a privat

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

'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

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

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.

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

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

An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galleries, and restaurants of downtown Edgartown. Expansive lawns, mature landscaping, and a substantial swimming pool create a setting more often associated with properties well beyond the Village center, offering remarkable space for outdoor living, entertaining, and generations of summer gatherings. At the heart of the property is a distinguished five-bedroom, five-bath residence encompassing more than 3,100 square feet. Rich in authentic Vineyard character, the home is attributed to Frederick Baylies Jr builder of Edgartown's iconic Old Whaling Church, lending architectural significance to an already exceptional property. Yet it is the combination of land, location, and lifestyle that truly di

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

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

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