96 houses for sale in Menemsha

Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the surrounding natural landscape. In addition there is a one bedroom one bath guest cottage. The property features extensive parking and serene, tree-lined privacy back from the main road, serving as a peaceful getaway, investment property or year-round island home. Bring your personal updates and creative touch or begin anew and make this classic Chilmark estate your very own island legacy

Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved plans are attached. 47 Quenames Lot 1-B is also available

Bright and Airy Black Point Retreat with Deeded Beach Lot to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach. Thoughtfully designed, the home has a welcoming entry that opens into a light-filled open floor plan that flows seamlessly onto a screened porch and expansive sun deck, creating an ideal setting for indoor-outdoor living and entertaining. The upper level features a serene primary suite with peeks at the water and a private bath. The lower level offers a second bedroom, full bath, and additional living space. The unique layout provides comfort and privacy for family and guests. A substantial detached garage is complemented with a finished guest suite on the second floor with a bedroom and full bath,

Bright and Airy Black Point Retreat with Deeded Beach Lot to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach. Thoughtfully designed, the home has a welcoming entry that opens into a light-filled open floor plan that flows seamlessly onto a screened porch and expansive sun deck, creating an ideal setting for indoor-outdoor living and entertaining. The upper level features a serene primary suite with peeks at the water and a private bath. The lower level offers a second bedroom, full bath, and additional living space. The unique layout provides comfort and privacy for family and guests. A substantial detached garage is complemented with a finished guest suite on the second floor with a bedroom and full bath,

Beautifully designed and built Post and Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and til

Beautifully designed and built Post and Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and til

Abels Hill opportunity! Coastal living at its finest in this contemporary Abels Hill retreat, where south-facing ocean views and exceptional amenities define the lifestyle. Situated within one of Chilmark's most sought-after communities, the property enjoys exclusive access to the Atlantic Ocean, Chilmark Pond, and private association tennis courts. The property features a beautifully designed main house and a detached guest suite, offering five bedrooms and three full baths. Inside, the light-filled interior showcases soaring vaulted ceilings and a desirable south-facing orientation, filling the home with natural sunlight throughout the day. A true chef's kitchen serves as the heart of the home, thoughtfully designed for both everyday living and effortless entertaining. Step outside to the expansive wraparound deck, where sweeping ocean views provide the perfect setting for morning coffee, al fresco dining, or unforgettable sunsets. Combining modern design, privacy, and premier access

Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevation and enjoys views of its small kettle pond, winter waterviews and the Sanctuary. There's also a sweet detached 1-br studio with bathroom. Its 5.45 acres offers open and sunny grassy lawns, mature trees and a small pond. The contemporary style home has open beamed ceilings, shiplap wood walls, two fireplaces, wood floors, and a spacious deck off the kitchen living area. The primary bedroom suite includes a separate sitting area, built-in bookshelves, and a private balcony

Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevation and enjoys views of its small kettle pond, winter waterviews and the Sanctuary. There's also a sweet detached 1-br studio with bathroom. Its 5.45 acres offers open and sunny grassy lawns, mature trees and a small pond. The contemporary style home has open beamed ceilings, shiplap wood walls, two fireplaces, wood floors, and a spacious deck off the kitchen living area. The primary bedroom suite includes a separate sitting area, built-in bookshelves, and a private balcony

This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows and a slider that leads out to a spacious deck. There is a second floor primary with ensuite bath, walk-in closet and private deck. Large family room with skylights and built-ins. There are two first floor bedrooms that share a bath, full basement, wood floors, a whole house generator and Oil FHW heat and new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens and plantings. There are also beautiful fruit trees; peach, pear and app

Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha's Vineyard-perfect as a primary residence, vacation home, or long-term investment in one of the island's most desireable natural settings

Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved plans are attached. 47 Quenames Lot 1-B is also available

Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard - a property that has brought multiple families together over generations of summers. For those seeking an authentic connection to the Vineyard's natural beauty and storied past, this is a rare and remarkable find

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite.

New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet kitchen, adjacent butler's pantry and vast open living area with wood burning fireplace, mellow wood floors and breathtaking views out every window. Four large bedrooms, three bathrooms plus a powder room. Primary suite bathroom features an independent tub and steam shower. Fully heated, insulated and air conditioned this home is four season living. Walking paths to pond access for kayaking, swimming and boating and association tennis court. This property is protected by a Trustees of Reservation Deed of Conservation Easement

Sited on 3.94 acres in the North Tabor Farm subdivision, this flexible 3-4 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and the heated, saltwater, 50x25x12 in-ground Pebble-Tek pool and pool house. There is an eat in kitchen with ample cabinetry and leathered granite countertops. Doors open onto the rear deck for outdoor entertaining. A guest bedroom, full bath, laundry and hallway lined with built in shelves are found on this level. Two dedicated office spaces-one on each level-provide exceptional flexibility. The upper office offers a vaulted ceiling with exposed beams, wide plank flooring, large windows, and sliding glass doors and sleeping loft. The lower office includes cork flooring, built in bookcases, large wi

Magical waterfront Quitsa pond cottage with private dock will change your life living on the water. Every day is special when you have an intimate relationship with Quitsa Pond. Calm, safe and breathtaking, adventure is out the doorstep and the sunsets. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates the simplistic beauty of this property. A rare and unique inspirational built-in art installation by Andy Goldsworthy adorns the northeastern wall of the living room. A fireplace created with slate roof tiles unlike any other is built into the southwest wall. Custom Will Parry windows and doors throughout with giant floor to ceiling glass doors that slide wide to join the inside and outside of the home bringing the natural beauty of the area into the house. Step outside and onto your private dock with power and water where you can keep 3 boats,

Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of some art and a few other items and has everything you need to enjoy your summers in Chilmark as you plan for your future. The property has a 4-bedroom septic system. Broker has ownership interest. TENANTS IN PLACE; 48 HOURS ADVANCE NOTICE FOR SHOWINGS PLEASE

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite.

A wonderfully private, peaceful aerie in Chilmark on 3 acres (with a Guest House), featuring a spacious, high, secluded, wrap-around Deck off of the Living Room and Dining Room. The house is built into the side of a hill which allows more light and 2 areas to be considered ground level. There is a soaring cathedral ceiling with cross beams, tying the room together with its almost 2- story, large, stone fireplace, in a warm caramel - colored glow. Ample flagstone terrace off of the glass - enclosed, light - filled dining room and a stone wall, sloped, grassy hillside out back, with lots of lawn on the front and sides. 4 Bedroom House and 3 Bedroom Guest Cottage. 7 Bedrooms total one 2-season bedroom is detached, with a 7 bedroom Septic = 2 Septic Systems. To reach the Lower Level private apartment (sans kitchen) in the Main House, head down the stairs from hall off of the living room. The lower level living quarters has its own, separate, ground floor entrance including a small Flagston

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming living room, anchored by a pristine Vermont Castings wood stove, opens seamlessly to a covered porch and spacious deck-perfect for morning coffee or evening gatherings. The spacious first-floor primary suite provides a private retreat with two en-suite baths and two walk-in closets. Upstairs, you'll find two bedrooms with beautiful wood floors, built-in drawers, and cabinets that add both charm and functionality to the rooms. These bedrooms share a hall bath, making the second floor an ideal space for family or guests. A generous bonus room above the garage offers flexible space for a home office,

Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevation and enjoys views of its small kettle pond, winter waterviews and the Sanctuary. There's also a sweet detached 1-br studio with bathroom. Its 5.45 acres offers open and sunny grassy lawns, mature trees and a small pond. The contemporary style home has open beamed ceilings, shiplap wood walls, two fireplaces, wood floors, and a spacious deck off the kitchen living area. The primary bedroom suite includes a separate sitting area, built-in bookshelves, and a private balcony

Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large deck and the rolling lawn. Come see this property to truly appreciate it

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite.

Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the primary bedroom. The expansive screened porch effectively doubles the living room, offering an enchanting area for relaxation or gatherings. Tucked just beyond the main house is a versatile barn with its own half bath, currently set up as a rec room and gym, great for guests and entertaining. There are three outdoor showers, full insulation and mini-splits throughout for heat and A/C. The yard is expansive and private, with room to dream-gardens, a pool, or just wide-open space to roam. Best part of all, ownership at Black Point Beach is included, so you can easily bike, stroll or drive down the qui

Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom home sits on one lot with two detached studios alongside. Close to nature, this seasonal home (April through October) was built in 1973 and evokes an earlier and simpler time. Use as is, build anew or significantly expand and/or modify the existing dwelling. There is a second abutting buildable lot with many options as well. Enjoyed as a summer retreat by one family for three generations, this is the only private home on Black Point Pond. Walking into the generous, inviting wood panelled living room, the eye is drawn to the large windows opening to expansive views. Rolling meadows, pond, and endless sea and sky. this blend of fields and water stretching into the horizon is the property's

Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark's coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly pastoral sensibility. A classic barn, two run-in horse stalls, a fenced field, and a coop support equestrian pursuits or a small gentleman's farm-an increasingly uncommon offering in Chilmark at this price point. The open acreage invites outdoor living, from summer entertaining and gardening to quiet enjoyment of the surrounding landscape and privacy. Inside, the home balances antique charm with thoughtful updates. Four bedrooms and three full baths include two main-level bedrooms and two second-floor en-suite guest rooms, creating a comfortable and flexible layout for hosting family and friends.

Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom home sits on one lot with two detached studios alongside. Close to nature, this seasonal home (April through October) was built in 1973 and evokes an earlier and simpler time. Use as is, build anew or significantly expand and/or modify the existing dwelling. There is a second abutting buildable lot with many options as well. Enjoyed as a summer retreat by one family for three generations, this is the only private home on Black Point Pond. Walking into the generous, inviting wood panelled living room, the eye is drawn to the large windows opening to expansive views. Rolling meadows, pond, and endless sea and sky. this blend of fields and water stretching into the horizon is the property's

Stylized Private Waterfront Retreat close to town perched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes throughout. From the moment you arrive, you're greeted by a graceful balance of architecture that blends with the landscape and affords contemporary touches. Vaulted ceilings, exposed beams, and hardwood floors create a warm, welcoming atmosphere, while expansive windows invite natural light and frame views of the water and extensive gardens. Off of the kitchen is a generous screened in porch which serves as an additional living space with views to the Tisbury Great Pond and manicured lawn. This is a sweet connector space to the primary bedroom wing which includes a private deck, spacious bathroom and walk-in clos

This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows and a slider that leads out to a spacious deck. There is a second floor primary with ensuite bath, walk-in closet and private deck. Large family room with skylights and built-ins. There are two first floor bedrooms that share a bath, full basement, wood floors, a whole house generator and Oil FHW heat and new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens and plantings. There are also beautiful fruit trees; peach, pear and app