Tucked away on more than two acres along a private dirt road, this extensively updated post-and-beam home offers exceptional space and privacy in a peaceful Aquinnah setting. The property is surrounded by woodlands, open fields, streams, and ancient stone walls and is located approximately one mile from Aquinnah’s resident beaches. The four-bedroom, three-and-a-half-bath home offers generous living space across three levels. Designed with gathering and entertaining in mind, the main level features a spacious kitchen with abundant counter and cooking space, a formal dining room, a fireplaced living room, and an additional living and entertainment area. Sliding doors open to an expansive deck spanning the back of the home—an inviting setting for outdoor dining, relaxing, and enjoying evening sunsets. A large outdoor shower completes the Vineyard experience. Upstairs, the oversized primary bedroom includes an adjoining room ideal for a home office, fitness area, or quiet retreat. Two additional bedrooms, a full bath, and a spacious bonus room provide flexibility for family and guests. The lower level offers a separate guest area with a sitting room, the home’s fourth bedroom, a full bath, and its own exterior entrance. An extra-deep two-car garage is located beneath the home and is accessible from both inside and outside, with additional space at the rear for a workshop or storage. A country-style shed and adjoining concrete patio create another outdoor gathering area, ideal for a fire pit and enjoying the property’s natural surroundings. The current owners have completed an extensive range of renovations, upgrades, and improvements—far too many to list here. Please inquire for the complete list. Conveniently located near the Aquinnah Public Library, Gay Head Lighthouse, the Aquinnah Cliffs, beaches, shops, and restaurants, this spacious up-Island retreat offers room to gather, entertain, and enjoy the beauty of Aquinnah. Excellent rental history—details provided upon request.
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.
Courtesy: Studio Realty LLC
508-687-2699
Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
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. Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses. 2 miles to Lucy Vincent beach
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.
Beautifully designed and built Post & 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 tile.
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.
Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.
Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.
There is a town at the end of Martha's Vineyard. The road narrows, the houses thin, and the light changes. This is Aquinnah; the westernmost town, clay cliffs, a lighthouse, and one of the smallest year-round populations on the Vineyard. Compound-scale offerings rarely come to market here. 19 Locust Lane is one of them. Nearly 17 acres high above Vineyard Sound, with open water views to the Elizabeth Islands. A custom Dutch Colonial main residence and separate guest house, both built in 2005. Cedar shake. Stone walls. Built to belong to the landscape, not compete with it. Inside: over 6,000 square feet across six bedrooms. Wide-plank floors, an open-plan dining room, and a gourmet kitchen with a Tuscan oven. At its center, a great room with cathedral ceiling, cedar trusses, and a floor-to-ceiling stone fireplace, facing the ridgeline and water beyond. Room to host, with the flexibility of two living spaces. Aquinnah has kept its character. This is the place that lets you stay there.
A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.
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 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows & a slider that leads out to a spacious deck. Second floor primary w/ensuite bath, walk-in closet & private deck. Large family room with skylights & built-ins. Two first floor bedrooms w/full bath, basement, wood floors, a whole house generator, Oil FHW heat & new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens & plantings. Beautiful fruit trees, a garage & shed. The property is gated and entirely enclosed with deer fencing.
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.
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.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access. The beautifully manicured path, leads from the house to the dock, where you can launch across the pond to your own private South Shore beach lot, included in this sale. Of course the new owner also has access to iconic Lucy Vincent and Squibnocket beaches. The property is surrounded by over seven acres of abutting conservation land. The grounds are meticulously designed, with mature landscaping and gardens that feel both timeless and intentional. This is more than a residence. It's the key to embracing the Chilmark lifestyle defined by privacy, water access, and understated elegance.
Courtesy: Sandpiper Realty Inc
508-627-3737
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.
Perched on 2.7 acres in one of Aquinnah’s most stunning settings, this coastal retreat captures sweeping views over the Atlantic and Noman’s Land. The main level offers an open living/dining/kitchen wrapped in windows and opening to a wraparound mahogany deck—ideal for sunrise coffee and sunset dinners. A Viking-equipped kitchen and a spacious ocean-facing primary suite complete this floor. The lower level includes two bedrooms, a large flex room with walkout stone patio, plus a full bath, laundry, and storage. Beautiful grounds feature custom stonework, garden beds, and multiple outdoor seating areas. A two-level workshop/studio with plumbing, electricity, and a wood stove offers excellent potential, including a future ADU with permitting. Directly across the street, the new Squibnocket Pond Reservation provides trail access to a pristine shoreline. Move-in-ready, private, and perfectly sited—this is Aquinnah at its best.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm--a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the island's premier luxury builders. Inspired by traditional New England farmhouse architecture, the exterior features cedar shingles, multiple gables, and timeless charm. At the heart of the home is a stunning chef's kitchen with soapstone countertops, a custom farm sink, high-end appliances, and a walk-in pantry. Two living rooms flank the kitchen, while the first-floor primary suite occupies the sunny southern end of the house offering luxurious comfort and ocean views. Four additional bedrooms and a two-car garage sit in a separate wing. Outdoors, the organic landscaping showcases historic stone walls, colorful gardens, and a manicured lawn, all complemented by nearly 3 acres of fenced pasture. This is more than a home, it's a lifestyle. Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farma 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the island's premier luxury builders. Inspired by traditional New England farmhouse architecture, the exterior features cedar shingles, multiple gables, and timeless charm. At the heart of the home is a stunning chef's kitchen with soapstone countertops, a custom farm sink, high-end appliances, and a walk-in pantry. Two living rooms flank the kitchen, while the first-floor primary suite occupies the sunny southern end of the house offering luxurious comfort and ocean views. Four additional bedrooms and a two-car garage sit in a separate wing. Smart features include Nest thermostats and a HEOS sound system. Outdoors, the organic landscaping showcases historic stone walls, colorful gardens, and a manicured lawn, all complemented by nearly 3 acres of fenced pasture. Enjoy outdoor living from the expansive back deck or the screened porch with stone fireplace, both perfect for stargazing or enjoying the breathtaking Atlantic Ocean views. Squibnocket Farm ownership includes exclusive access to scenic trails, pond launches, and a private beach with some of the Martha's Vineyard's most pristine dunes and shoreline. This is more than a home, it's a lifestyle.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
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. Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses. 2 miles to Lucy Vincent beach
Chilmark is located in Massachusetts. Chilmark, Massachusetts 02535has a population of 1,460. Chilmark 02535 is less family-centric than the surrounding county with 11.15% of the households containing married families with children. The county average for households married with children is 27.66%.
The median household income in Chilmark, Massachusetts 02535 is $104,716. The median household income for the surrounding county is $77,392 compared to the national median of $69,021. The median age of people living in Chilmark 02535 is 53.5 years.
The average high temperature in July is 80.1 degrees, with an average low temperature in January of 22.6 degrees. The average rainfall is approximately 47.3 inches per year, with 30.1 inches of snow per year.
