422 properties for sale in 02557

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style. First showings 7/12/26

Wonderful opportunity to secure a piece of the Vineyard at a great price. This home allows you access to Lambert's Cove Beach as well as access down the paths and dirt road to Long Point Reservation, a mere 15-minute bike ride away. With a contemporary flair, this home needs some work and is ideal for someone looking to build sweat equity or create community or workforce housing. The interior exudes a hybrid post and beam feel with a lot of wood and high ceilings in the main room. A bedroom and loft upstairs share a bath, and the loft can easily be closed off from below. Downstairs the house is built as a slab with oak floors and there are 2 sunrooms used for passive solar gain that have tons of light and brickwork and with modification could be bedrooms. The Livingroom has a beefy woodstove to supplement the Kerosene monitor and Mini split. This home could easily have solar and be self-sufficient. Built on 1.4 spacious acres of flat land with a large deck off the back, this fixer-uppe

Wonderful opportunity to secure a piece of the Vineyard at a great price. This home allows you access to Lambert's Cove Beach as well as access down the paths and dirt road to Long Point Reservation, a mere 15-minute bike ride away. With a contemporary flair, this home needs some work and is ideal for someone looking to build sweat equity or create community or workforce housing. The interior exudes a hybrid post and beam feel with a lot of wood and high ceilings in the main room. A bedroom and loft upstairs share a bath, and the loft can easily be closed off from below. Downstairs the house is built as a slab with oak floors and there are 2 sunrooms used for passive solar gain that have tons of light and brickwork and with modification could be bedrooms. The Livingroom has a beefy woodstove to supplement the Kerosene monitor and Mini split. This home could easily have solar and be self-sufficient. Built on 1.4 spacious acres of flat land with a large deck off the back, this fixer-uppe

This traditionally styled residence offers exceptional quality and craftsmanship in a coveted Edgartown location, situated on a corner lot just blocks from downtown and the harborfront. Thoughtfully designed for both elegant entertaining and relaxed island living, the home features beautifully proportioned interiors that flow seamlessly from one space to the next. The inviting front foyer opens to a gracious living room with fireplace and French doors leading to a deep, covered porch complete with its own fireplace. The 1st floor continues to a private den with fireplace, while the dining room and spacious kitchen/family room complete the main living spaces. Abundant windows and French doors throughout the 1st floor provide an effortless connection to the covered porch and the beautifully landscaped grounds. The 2nd floor offers 4 well-appointed bedrooms and 3 full baths providing comfortable accommodations, with most bedrooms offering access to private 2nd-floor decks. The finished lo

Set in a private community, Sweetened Water Farm offers the pastoral charm of Martha's Vineyard's rural up-island, just minutes from the energy of downtown Edgartown. Residents share access to the association's horse barn and common pastures, ideal for keeping horses or other livestock, adding to the farm's authentic agrarian character. This custom-built home is a true Vineyard gem, crafted over time by local artisans and set against sweeping pastoral views. The main house currently offers 3 bedrooms and 2 bathrooms, with the potential to expand to 6 bedrooms, as approved by the Edgartown Board of Health and Building Department. Inside, the home tells its own story: African mahogany millwork in the library, massive fieldstone fireplaces, and a Jotul wood stove. Built to the same exacting standard, the barn and garage include a custom wood-fired sauna and a two-room office on the second floor

This mixed use building is zoned for residential and commercial use. It is extremely well built with an emphasis on non-toxic materials throughout. High ceilings on all three levels. There are radiant floors mixed with forced hot air/AC. The building offers a variety of uses for a new owner. The existing spaces are very versatile and would be ideal for any service oriented business given the multiple office spaces and a large open room for perhaps physical therapy or treatment space. There is a galley kitchen and two full baths on the main floor as well as three offices (one could be considered a first-floor bedroom), and a large open room with doors out to the parking area. Upstairs, there is a two-bedroom apartment with a full bath, a full kitchen with wood cabinets, and a living room with a fireplace. In addition to the finished apartment, there is a separate space framed and insulated with generous square footage to easily expand the living space or bedroom capacity in the second-f

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the

Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from the updated kitchen into a living room centered around a classic brick fireplace. Skylights bring in additional sunlight, while sliding doors open to expansive new south-facing decks-perfect for outdoor dining, entertaining, and relaxing after a day at the beach. The third floor provides a second living area, bedroom, and private half bath. A full basement offers ample storage and potential for additional finished living space. The detached two-car garage includes a private one-bedroom apartment above with its own wraparound deck. A bonus room with a half bath on the garage's main level is ideal for an office. A c

Privately nestled amid sweeping gardens and lush natural landscaping, this 3-bedroom, 3-bath home offers the perfect blend of timeless design and refined contemporary living. Thoughtfully curated interiors feature an open-concept living area, a large kitchen with Viking cooktop, Fisher and Paykel dishwasher and quartz countertops, inviting dining spaces, and comfortable gathering rooms filled with natural light. French doors open to a brick patio with fireplace, surrounded by mature gardens, creating seamless indoor-outdoor living ideal for entertaining or quiet relaxation. With beautifully designed indoor and outdoor spaces in the heart of Katama, this property is a true Vineyard sanctuary

A beautiful pastoral, private family compound in West Tisbury, on 7.5 glorious acres of meadow comprised of two parcels, offers a rare opportunity. Elias Lane is a quiet country road tucked behind Misty Meadows and just minutes from West Tisbury village. The property features a lovingly maintained 4 BDR main house with a well appointed kitchen, recent sun porch addition an elegant Lew French stone fireplace. The primary bedroom is on the first floor and all the bedrooms feature peaceful meadow views. The 2 BDR post and beam barn guest house has a deck and plenty of separate storage space. There is a private tennis court and large heated swimming pool. The additional parcel is 40 Elias Lane, flat and buildable land. Build another home or sell the subdivided second lot in the future - there are so many possibilities

Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure - a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together. Set on a generous.26-acre R10 parcel, this three-bedroom home offers the warmth and craftsmanship of an earlier era, with original architectural details, beautiful wood floors, classic moldings, built-ins, a fireplace, and sun-filled rooms framed by garden views. Thoughtfully cared for over the years, the home retains the authentic charm and easy elegance that make historic Vineyard cottages so beloved. The heart of the home is its connection to nature. Oversized windows invite the gardens inside, filling the living spaces with natural light and views of established plantings, stone pathways, and quiet outdoor sitting areas. Whether enjoying morning coffee overlooking the gardens, gathering by the firepl

Experience the timeless beauty of Martha's Vineyard from this luxurious waterfront retreat where the landscape feels so effortlessly connected to daily life. This property embodies understated luxury and timeless design, featuring a meticulously crafted stone residence and guest house. The setting overlooking Edgartown Great Pond has a sandy pond beach and deeded access to the pristine Atlantic Ocean Beach. Ospreys and redtail hawks soar overhead in this naturalized setting that is only 13 minutes to Edgartown village or the MV airport, yet a world away. This is a rare combination of privacy and proximity. An opportunity to own one of the Vineyard's most distinctive properties. The home was thoughtfully designed to embrace its exceptional surroundings; the residence is filled with natural light and enjoys beautiful water views. Custom floor to ceiling sliding doors invite the outside in. Spacious interiors flow easily to inviting outdoor living spaces, enhanced by a swimming pool, walk

Privately nestled amid sweeping gardens and lush natural landscaping, this 3-bedroom, 3-bath home offers the perfect blend of timeless design and refined contemporary living. Thoughtfully curated interiors feature an open-concept living area, a large kitchen with Viking cooktop, Fisher and Paykel dishwasher and quartz countertops, inviting dining spaces, and comfortable gathering rooms filled with natural light. French doors open to a brick patio with fireplace, surrounded by mature gardens, creating seamless indoor-outdoor living ideal for entertaining or quiet relaxation. With beautifully designed indoor and outdoor spaces in the heart of Katama, this property is a true Vineyard sanctuary

Fantastic opportunity for a great locationb and a spacious custom designed home! This house is well sited to offer maximum privacy in the lush area of Long View, a short bike ride to Lambert's Cove beach. It's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the outdoors. A sunny dining area with French doors connects you to the deck and back yard. The large spacious eat in kitchen has a wood stove and comfortable siting area and also a deck off of it that walks out to a brick barbeque, where you can chef up some great meals in the afternoon sun. Upstairs on one side is a huge ensuite primary bedroom with a walk out to a small deck on one side. There are 3 additional comfortably sized bedrooms with a shared bathroom also on the 2nd floor. A huge 1st floor laundry room could be converted into a bedro

Just 9/10 of a mile from Lambert's Cove Beach, this beautifully renovated tri-level home offers over 4,000 square feet of thoughtfully designed living space with six bedrooms and six bathrooms. Expanded and extensively updated in 2023, the home provides exceptional flexibility for entertaining and accommodating family and guests. A spa-like backyard features an inviting in-ground pool and hot tub with a waterfall, surrounded by patios, classic stone walls, mature landscaping, and vibrant blue hydrangeas, offering a private, tranquil island retreat. The top-level features an expansive sun deck with water views of Vineyard Sound, creating the perfect setting for relaxing or enjoying spectacular sunsets. Inside, generous living spaces span three levels, complemented by a beautiful gym overlooking the outdoor stone terraces and patios. A detached one-car garage includes unfinished space above, presenting an excellent opportunity for a future home office, studio, or recreation room. Ideally

Lambert's Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms and 3 bathrooms in Main and 2 bedrooms and 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor and granite counters with stainless steel appliances and gas 4 burner cooktop and double wall oven. Dining area with lots of natural light and 2 sliding glass doors lead out to the deck and patio. Off the pantry hallway, is a full bathroom (with glass block tiled shower), open Livingroom area with cathedral ceiling, with wide pine floors, home office. A slider leads to a covered porch and back deck. Au pair suite bedroom with loft and separate full 3/4 bathroom-with glass slide to deck and outdoor shower and own entrance. Another large bedroom is located just off the living room. The back of the house is wrapped with a 30x20

A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you will find two large bedrooms, a full bathroom with walk-in shower and plenty of attic storage. Set on a picturesque two-acre parcel, the property also features a detached 384-square-foot studio, which sits privately from the main house, with a private parking area, yard, and septic system, it presents wonderful possibilities for hosting family and friends or creating a private artist's studio or home office. Ideally located just minutes from Nip 'n Tuck Farm, Up-Island Cronig's Market, Conroy's Apothecary, and Main St. in Vineyard Haven. As a W. Tisbury resident, you'll also enjoy access to the

Great Location Cape Cod style year round home well maintained on a private dead end road close to Tashmoo Landing. New roof 2025, new windows, basement insulation replaced. A solid well built home ready for new owners to enjoy! Open concept kitchen to dining room. Three bedrooms and one full one half bath. Additional living area with full clean dry basement adds 768 SF with egress walkout door and large windows letting in natural light. The house has propane monitors, mini splits for cooling/heating as well as window A/C units on the second floor with backup electric baseboard. The property is in the Tashmoo Watershed and will need an enhanced system per the Town installed by the buyer. This is a fantastic area just minutes to Tashmoo landing, tennis, pickleball, boating, fishing, kayak storage, kayaking, Mink Meadows Golf, Tashmoo Town Beach, Tisbury school, Downtown Main Street and the year round Ferry Terminal

This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design, fosters positive and sustained interaction and relationships among people and the natural environment. The entrance to the home leads across enormous granite steppingstones bridging over expansive reflection ponds with two waterfalls cascading to a lower-level pond. The entry way welcomes one to open and dramatic living spaces with 10 ft ceilings and large expanses of glass facing Vineyard Sound and the surrounding landscape. In the main residence, each of the five-bedroom suites have unique features and connect with the beauty of the outdoors. The lower level of the residence offers amazing, ey

Great Location Cape Cod style year round home well maintained on a private dead end road close to Tashmoo Landing. New roof 2025, new windows, basement insulation replaced. A solid well built home ready for new owners to enjoy! Open concept kitchen to dining room. Three bedrooms and one full one half bath. Additional living area with full clean dry basement adds 768 SF with egress walkout door and large windows letting in natural light. The house has propane monitors, mini splits for cooling/heating as well as window A/C units on the second floor with backup electric baseboard. The property is in the Tashmoo Watershed and will need an enhanced system per the Town installed by the buyer. This is a fantastic area just minutes to Tashmoo landing, tennis, pickleball, boating, fishing, kayak storage, kayaking, Mink Meadows Golf, Tashmoo Town Beach, Tisbury school, Downtown Main Street and the year round Ferry Terminal

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

This mixed use building is zoned for residential and commercial use. It is extremely well built with an emphasis on non-toxic materials throughout. High ceilings on all three levels. There are radiant floors mixed with forced hot air/AC. The building offers a variety of uses for a new owner. The existing spaces are very versatile and would be ideal for any service oriented business given the multiple office spaces and a large open room for perhaps physical therapy or treatment space. There is a galley kitchen and two full baths on the main floor as well as three offices (one could be considered a first-floor bedroom), and a large open room with doors out to the parking area. Upstairs, there is a two-bedroom apartment with a full bath, a full kitchen with wood cabinets, and a living room with a fireplace. In addition to the finished apartment, there is a separate space framed and insulated with generous square footage to easily expand the living space or bedroom capacity in the second-f

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residence-an architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking t

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

Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living. The three-bedroom main residence is complemented by a separate two-bedroom guest house, creating a flexible and highly desirable arrangement for extended family, guests, or income potential. The layout lends itself effortlessly to both everyday living and entertaining, with each structure offering its own sense of space and privacy. A substantial garage adds meaningful utility, ideal for storage, a workshop, or accommodating island vehicles, an increasingly valuable feature in this location. The grounds offer ample room for outdoor living and future expansion, allowing the next owner to tailor the property to their vision. Surrounded

Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living. The three-bedroom main residence is complemented by a separate two-bedroom guest house, creating a flexible and highly desirable arrangement for extended family, guests, or income potential. The layout lends itself effortlessly to both everyday living and entertaining, with each structure offering its own sense of space and privacy. A substantial garage adds meaningful utility, ideal for storage, a workshop, or accommodating island vehicles, an increasingly valuable feature in this location. The grounds offer ample room for outdoor living and future expansion, allowing the next owner to tailor the property to their vision. Surrounded

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residence-an architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking t

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

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with strong rental history!