Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit! Surrounded by ancient stone walls on three sides and mature trees, the land has stunning sunset skies, lovely pastoral views, and potential second-floor water views to the Vineyard Sound. The sounds of nature, and the beloved distant Menemsha bell buoy will quietly become a part of each day. A walking path takes you to Menemsha's historic harbor and beach in just 10 minutes for waterfront dining, local fish markets, boutique shopping, art galleries, and the timeless charm of village life. Chilmark residents' access to nearby Lucy Vincent, Squibnocket, and Menemsha beaches invites days of swimming and sunset walks along the shore. The Seller has surveyed and staked the property lines and building envelope, a partially installed 6 bedroom septic, and has architectural plans from well-known and respected MV-based Sullivan and Associates.

This quiet and lovely four-and-a-half-acre lot in Chilmark is READY TO BUILD. The land has a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation, NHESP has been completed and there are no restrictions on the lot, there's a septic design and the well has been installed. This means so many outstanding possibilities for a future Buyer to build their dream home on this special piece of land. Peaceful and private location right next door to the 184 acres of conservation land at Waskosim's Rock Reservation, with miles of walking trails. An accessory dwelling is also possible. The lot is part of the Old Farm Road Association tennis allowing a future owner use of the community tennis courts, just across Old Farm Road. Enjoy access to the ocean beaches of Lucy Vincent, and Squibnocket. Architectural plans by Peter Breese for a 4-bedroom home and 2 car garage - current owner is willing to share with a Buyer. NOTE: Larger septic and home possible.

Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of arrival, while the property itself is adorned with beautiful glacial rock formations that add texture and distinction to the landscape. Surrounded by 23 acres of protected land to the southeast, including Roaring Brook Ravine and across Tabor House and along Middle Line for an additional 45+ acres of MV Land Bank ensuring privacy and an unspoiled natural backdrop. Preliminary engineering has been completed and the well is being installed by the Seller. The septic design, plan and installation is the responsibility of the buyer. Substantial infrastructure work has been completed through clearing and road installation. A special offering where nature and opportunity converge. **abutting 3.4 acre parcel with Guest House is also for sale, please inquire**

Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway leads to the kitchen. Double sliding doors and circular windows provide the space with natural light, creating an open, airy atmosphere throughout. The layout features two guest bedrooms — one off the living area and one off the kitchen — sharing a full bathroom with a shower/tub combo. The primary bedroom, situated just beyond the kitchen, enjoys its own full bathroom and a private exterior door to the deck. A laundry/utility room next to the primary bedrooms provides access to an outdoor shower— a beloved Martha's Vineyard staple. Near the laundry room is a staircase leading to a bonus room upstairs. A large two room shed with a loft to store your beach/fishing gear or to use as a workshop rounds out the property. Whether you're searching for a summer retreat or a forever home, this is a rare opportunity to plant roots in Chilmark. Property offered "AS IS".

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 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 survey is attached. 47 Quenames Lot 1-C is also available.

Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort and ease for seasonal and year-round living. The land offers room to grow, with exciting expansion possibilities subject to town approvals. Whether you envision a quiet island retreat, an investment opportunity, or a future compound, this Chilmark gem offers endless possibilities and timeless Vineyard appeal. **abutting 4.28 acre parcel is also for sale, please inquire***

This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected conservation land of Menemsha Hills, the property enjoys a natural buffer along with direct access to scenic walking trails and some of Chilmark’s most iconic views. Ideally located just a short distance from Menemsha and Chilmark Center, it offers both seclusion and accessibility. Homeowners will also have access to Lucy Vinecent and Squibnocket beaches as Chilmark property owners. With an established rental history and full winterization for year-round use, this home is well-suited for both personal enjoyment and income generation. For those seeking a foothold in one of Martha’s Vineyard’s most desirable towns, this is a compelling opportunity not to be missed. Available to show on weekends with 24 hours notice.

Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, 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 desirable natural settings.

Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spacious deck. The first-floor primary suite offers two en-suite baths and two walk-in closets, while two second floor bedrooms boast wood floors, built-ins, and a shared hall bath. A bonus room above the garage provides additional space for a home office, workout space, or studio. The private backyard, outdoor shower, garage, basement, and generator complete this exceptional property. A separate studio with an open floor plan, bath, and loft, separate from the main house, adds further versatility. Close to Lucy Vincent Beach, the center of Chilmark, and all West Tisbury has to offer, this property is ideal as a year-round home, seasonal retreat, or investment.

A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on the island today. The parcel directly abuts the nearly 80 acres of conservation land at the Martha’s Vineyard Land Bank Peaked Hill Reservation. This unique adjacency significantly enhances the sense of scale while ensuring that the surrounding landscape remains protected and preserved. Buyer is responsible for due diligence including engineering, utilities and permitting. Some wetlands are present. This is a rare chance to secure substantial acreage in Chilmark with historic character, enduring privacy, and direct connection to preserved conservation land — an ideal setting for a legacy Vineyard property.

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. 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.

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. Living spaces are warm and inviting, with a masonry double fireplace, preserved period details, and an updated kitchen and baths. Recent improvements include HVAC, windows, insulation, and a five-bedroom septic system, offering flexibility for future expansion and barn renovation. Located steps from West Tisbury village, Alleys General Store, the library, the Yoga Barn, the Grange Hall and nearby conservation trails, the setting combines convenience with the privacy and natural beauty that define Chilmark. A distinctive Vineyard offering with uncommon versatility—equally suited as a summer retreat, year-round residence, or small-scale farmstead.

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 apple! The property is gated and entirely enclosed with deer fencing. There is also a storage shed and a detached garage. Easy access to Menemsha, Chilmark Store and Chilmark Beaches. Outdoor surveillance system on premises, audio and video.

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.

Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in place, buyer responsible for new septic system. Fire destroyed house in 2020. See old and new views in document attached.

Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home. A must-see to appreciate all the special touches throughout the Main House, Guest Camp, and Garage.

This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience — just minutes from Lucy Vincent and Squibnocket beaches, and the historic fishing village of Menemsha. Engineering for wells and home sites is complete and utilities are on site. Architectural plans by Morgan Studio for a multi-home compound with a swimming pool and accessory structures are available for review upon request.

This Chilmark home is one-of-a-kind - a warm, charming hideaway set on 4.4 spectacular acres just off North Road. At the top of a shady driveway you are met by stone walls so typical of Chilmark from a bygone era. You enter a courtyard through cedar gates where you find beautifully tended flower beds. The porch is the ideal location for you to enjoy the private, peaceful courtyard. Immediately upon entering the home you captivated by the warm ambience. The main living spaces and primary bedroom suite all showcase views of a sweeping meadow punctuated by granite boulders and stately oaks. In addition to the primary bedroom suite and additional sleeping spaces on the main level, there is a large finished lower level with private entrance - ideal for accommodating your guests. Back upstairs and across the courtyard, there is an unfinished structure with screened porch begging to be converted into a bunkhouse for the kids, if not a studio or office. There are two garage spaces for cars or boats. Visitors are encouraged to walk the grounds and enjoy the private nooks and crannies of this magical piece of land. The property is less than 2 miles to Menemsha Village and Beach, 1 mile to the north shore beach at Great Rock Bight, and a 3-mile drive to parking at Lucy Vincent Beach.

Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace, dining area overlooking the pool and yard, air conditioning, and cable television and internet and a distant peek at the ocean. The home sleeps 8 comfortably, with two ensuite bedrooms (king and queen), an additional queen room, and a twin room perfect for guests or little ones. Outdoors you will find an inground, 4-foot-deep heated pool including pool side furniture, umbrellas, hammock, outdoor shower, and a gas barbecue. Step across the road to the Land Bank’s Fulling Mill Preserve and theOcean View Farm Preserve with stunning Atlantic views and 20+ acres of walking trails. As a Chilmark resident you will enjoy the beautiful beaches of Lucy Vincent and Squibnocket. This property has a strong rental history with rates ranging to $13,000 weekly. Easy to show, please call listing broker.

A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx.

Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you can enjoy swimming and watching beautiful sunsets. There is also a 1 car garage with a work space.

This 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 tiled baths, incredible workmanship throughout with an eye for style. warmth and comfort. There is also a generous laundry room with wash sink. The fully finished walkout basement includes a great room, finished utility room with a dog bath, workshop and a full bath with shower. Beautifully landscaped grounds with multiple perennial beds , vegetable gardens and surrounding stone retaining walls. Privately sited on 4.80 acres and potential for a guest house with proper town permitting after 5 years.

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, one up to 30 feet long. Walk down your boat ramp into the warm waters of the pond for a swim, kayak or paddleboard adventure. A custom staircase influenced by Frank LLoyd Wright has built-in book cases and metal work by artisan Whit Hanschka which brings you to the upper floor where there are 3 bedrooms and 2 baths. 2 of the bedrooms open out onto a small deck overlooking the pond and all have views of the water. This home is cozy with radiant floor heat under the tile floor and AC for the hot steamy summer nights. This house is one of a kind.

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 quiet dirt road for daily visits to the ocean! Approved eight-bedroom septic plan included.

STYLISH CHILMARK RETREAT WITH SWEEPING WATER VIEWS, PRIVATE BEACH, TENNIS, AND WALKING TRAILS. Set within the coveted Spring Point community, this beautifully renovated island retreat captures an unmistakable sense of place, where sweeping water views, natural beauty, and effortless indoor-outdoor living define the experience. Thoughtfully updated in 2022 under the direction of a talented architect/design-build team, the home blends relaxed coastal sophistication with warm, organic finishes, including driftwood-colored hardwood floors, a striking stone fireplace with a rough-hewn wood beam mantel, a sleek cook’s kitchen, custom-tiled bathrooms with distinctive design panache, and an integrated Sonos® sound system. Designed to embrace its spectacular setting, every room is framed by large windows and sliding glass doors that open to private decks with water views, creating a seamless connection to the outdoors. A spacious screened porch at the front of the house serves as the perfect gathering hub for morning coffee, quiet afternoons, summer dining, or easy entertaining. Surrounding the home, a handsome paver parking court and gorgeous, meticulously landscaped grounds enhance the property’s serene, retreat-like feel, while a charming gazebo offers a picturesque spot for relaxing, quiet meditation, or simply taking in the Island setting. The fully finished walk-out lower level offers flexible bonus living space, ideal for guests, recreation, media, or future expansion potential. Set within Spring Point’s 68 acres of common land, community amenities include three miles of ancient walking trails traversing old stone walls, two tennis courts, and Beck’s Beach, a three-quarter-mile stretch of private shoreline known for magnificent sunsets and views extending from the Elizabeth Islands all the way to the Gay Head Lighthouse. Located moments from Menemsha, Great Rock Bight, the Chilmark Flea Market, and other Up-Island favorites, this special Spring Point property offers a rare combination of privacy, natural beauty, community amenities, and timeless Vineyard appeal.

Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network. The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper level includes an open-concept kitchen, dining, and living area, along with a private primary suite and dedicated office space. There is a large open deck and a screened porch in this level, as well as a deck off the primary bedroom suite. Thoughtfully designed for both everyday living and entertaining, the home includes amenities such as air conditioning, whole-house generator, integrated sound system, outdoor lighting, and more. Outside, the grounds are equally impressive, featuring a tennis court, landscaped gardens with a water feature, and a large open meadow spanning several acres, all surrounded by mature woodland for exceptional privacy. No neighboring homes are visible from the property. There is ample room to add a swimming pool, and the parcel may offer subdivision opportunities. Ownership also includes rights to Brickyard Beach.

This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views of open pastures, ancient stone walls, woodlands, and the Atlantic beyond. The four-bedroom residence features an open-concept layout that seamlessly connects indoor living spaces to a full-length deck—perfect for entertaining or simply soaking in the peaceful surroundings. Recent updates include new kitchen appliances and a high-efficiency heat pump system with central air conditioning. A true highlight of this property is the land itself. There is an extensive network of trails winding throughout the property, leading through meadows and forest, past streams, a large pond and striking glacial erratics. This property has an extraordinary sense of place and feels like a private piece of up-island history—rich in character, natural beauty, and possibility. Six-bedroom septic installed. Abutting 3.9-acre building parcel available.

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 square feet of gracious living space. The sunny, light-filled main house showcases an open kitchen and living area anchored by a striking central fireplace—ideal for both everyday year-round living and entertaining. An expanded primary suite wing includes a spacious primary bedroom, full bath, bright office, half bath, and dedicated laundry. A second-story space offers flexibility as an art studio, office, or media room. A classic three-season living room invites relaxed enjoyment of the surrounding landscape, including distant winter waterviews. Well-suited for compound living, the property is perfect for the equestrian and includes a guest house, horse barn, fenced pastureland, garage, and an old boat shed—providing exceptional flexibility for family, guests, and a wide range of outdoor pursuits. Deeded access to Chilmark Pond and South Shore Beach offers a rare opportunity to enjoy swimming, kayaking, and some of the Island’s most beautiful and unspoiled coastline. This property has a seven-bedroom septic, full solar, and abuts acres of conservation land. Ideally located in the heart of Chilmark, the property is just minutes from Alley’s Store, Lucy Vincent Beach, Chilmark Tavern, Beetlebung Farm, the Chilmark Store, and more—perfectly capturing the essence of the Chilmark lifestyle and the very best of Vineyard living.

Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by acclaimed architects Jane & Christian Langmuir, this exceptional home is nestled on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace warmth, natural light, and its surrounding environment, the three-bedroom residence seamlessly blends natural elements with contemporary architectural details. The dramatic great room is anchored by a striking fireplace with a glacial stone hearth. The open kitchen is complemented by custom-crafted cabinetry and top-tier appliances. The primary suite includes two separate office spaces and a media space, a walk-in closet, and a spa-inspired bathroom. A private guest suite offers a full bath with a soaking tub, providing comfort and privacy for visitors. The third bedroom is currently configured as a gym and wellness space, complete with a sauna. The lower level includes an attached two-car garage. Designed with sustainability and ease of ownership in mind, the property features owned solar panels, an electric vehicle charging station, and a six-bedroom septic system, offering flexibility for future expansion. The striking entrance is highlighted by a beautiful stone patio and tranquil water feature. Surrounded by iconic stone walls, mature trees, the property offers a rare connection to the natural beauty of the Island. Residents of Seven Gates Farm enjoy access to 3 private beaches on Vineyard Sound, two docks, two tennis courts, and more than 1,000 acres of protected land—including vast open fields, woodlands, ponds and miles of walking trails. This is an extraordinary blend of privacy, community, and stewardship. A boat mooring can be transferred with the property. 2% fee paid to Seven Gates Farm at Closing. MV Land Bank fee is additional.

Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark—an offering not to be missed.

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.

Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn and 16' x 40' swimming pool. This thoughtfully designed post and beam main home was featured in Country Home magazine, and showcases wide-plank satin-finished oak flooring, soaring ceilings, custom cable rail staircases, and a striking double sided propane fireplace that anchors the living spaces. A screened porch extends the living area outdoors, offering both dining and lounge areas centered around another beautiful wood burning fireplace. A finished lower level adds additional square footage with a TV area plus pool and ping pong and a large utility space for laundry and storage. Outdoors, the elegance continues with climbing roses, classic stone walls, and a sweeping lawn that leads to the swimming pool and a traditional two car barn. Above the barn, a charming one-bedroom, one-bath suite provides a private retreat for guests. It's rare to find a home like this in Chilmark, combining a superior quality finished home with scale and style. All in a versatile setting - convenient to down-island while enjoying access to Chilmark’s coveted beaches and amenities.

Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a short walk to the Menemsha harbor, beach, boutique galleries, and fresh seafood restaurants—from the daily catch from local fish markets to the fine dining of the Home Port. To the Southeast, watch Menemsha Pond ebb and flow around sandy islands with 120 degrees of unobstructed view. To the Northwest, elevated rooms look out over the sunset on Menemsha Harbor. A secluded lawn is partially shaded by healthy blue spruce and bordered by an ancient stone wall. The dock traverses the estuary into a private cove opening. The property has a permit to extend the dock access from the property to 64’. This is a significant dock that can accommodate a power boat, sailboat, and multiple kayaks and paddleboards. Docks are no longer permitted on Menemsha Pond, making this an incredible opportunity for a waterfront house and guest house with a dock. This is a secure environment surrounded by water on three sides. The home is well built with quality hardwood floors, doors, and trim. The wood-burning fireplace has custom-built cabinetry and trim. Both the house and guest house are flooded with natural light due to the southern orientation. The property is set up for year-round water through the Menemsha Water Company, and a new 5-bedroom Title-5 compliant septic is installed. Unique remodeling and expansion ideas included in photos have been designed by Sullivan and Associates. The potential here is exciting compared with other waterfront island properties due to the existing height, large attic with views, and a lower walkout level with tremendous natural light, which together allow for valuable future living square footage. You are welcome to continue the legacy of this extraordinary real estate.

Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by Heikki Soikkeli, the house is light filled with 140 windows so every room has windows on 3 of the 4 sides. The house has 3 self contained bedroom wings and a stunning Lew French fireplace and chimney. The property sits on a private 48 ft elevated 425 ft setback site in the highly desirable Spring Point community -- 48 homeowners on 330 acres with 90 acres of common land, 2 tennis courts and 5 miles of quiet paths and pretty well maintained country dirt roads -- with the finest north shore bluff path along a 1 mile stunning private sandy beach abutting the dreamy Great Rock Bight Beach Cove next to the 200 acre Menemsha Hills Reservation. The house is a short walk on a grassy canopied path to the beach. The living room, primary bedroom and kitchen have grand water views.

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.

Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist’s studio, and a detached garage with an additional bedroom above — creating the ideal retreat for extended family, guests, or creative living. Expansive water views are showcased throughout the property, with inviting indoor and outdoor spaces designed to capture the natural beauty of the shoreline. Whether enjoying morning coffee overlooking the water, entertaining on warm summer evenings, or taking a short stroll to the private dock on Chilmark Pond, or boating over to the private sandy Atlantic Ocean beach,every aspect of this property embraces relaxed year-round coastal living. A truly unique offering, this compound presents an extraordinary opportunity to own a multi-generational retreat in an idyllic setting close to Chilmark town center as well as the conveniences of West Tisbury. The owners have plans for a pool and pool cabana if a new owner would like to pursue this, plan in documents attached to the listing.

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 & 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 & association tennis court. This property is protected by a Trustees of Reservation Deed of Conservation Easement.

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. 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.

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with 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 seasonal home sits on one lot with two detached studios alongside. Close to nature, this home was built in 1973 and evokes an earlier and simpler time. Enjoyed as a seasonal retreat by one family for three generations, this is the only private home on Black Point Pond. A short walking path leads from the house to a kayak rack on the pond. Paddle and explore Black Point Pond or walk, bike, kayak or drive to nearby Black Point Beach. These three lots (6 acres, 6 acres and 34 acres) are being offered together for the first time in over fifty years. Two of the lots (Lots 1 and 2) are buildable while the third lot (the Meadow Lot) provides view protection for lots 1 and 2 and frontage on beautiful Black Point Pond. A Black Point Beach lot is also included as part of this offering and will give a new owner membership in the private Black Point Beach Association. This is a rare opportunity to purchase an estate-sized parcel on Chilmark's south shore with enormous privacy, stunning views, private pond frontage, two buildable lots and access to one of the most spectacular beaches on Martha's Vineyard.

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 backyard. Gazing out from the two-story shingled home it's easy to imagine the legacy of this land, the family that grazed their sheep and for generations tended the land, and the more recent history over the last 50 years of family backyard cookouts, children catching crabs in the nearby creek and bike rides down the dirt road to idyllic Black Point Beach where expansive stretches of white sand run between Black Point Pond and the Atlantic Ocean. A short walking path leads from the house to a kayak rack on the pond. Paddle and explore the pond or walk, bike, kayak or drive to nearby Black Point Beach. These three lots (6 acres, 6 acres and 34 acres) are being offered together for the first time in over fifty years. Two of the lots (Lots 1 and 2) are buildable while the third lot (the Meadow Lot) provides view protection for lots 1 and 2 and frontage on beautiful Black Point Pond. A Black Point Beach lot is also included as part of this offering and will give a new owner membership in the Black Point Beach Association. This is a rare opportunity to purchase an estate-sized parcel on Chilmark's south shore with enormous privacy, stunning views, private pond frontage, two buildable lots and access to one of the most spectacular beaches on Martha's Vineyard.

Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive winds through scenic farmland and open fields, running along the edge of Quenames Cove before arriving at your own white sand beach and the Atlantic Ocean. The setting is defined by open land and natural surroundings, creating a sense of space, privacy, and uninterrupted views. The compound consists of five thoughtfully crafted structures. The original 1842 Farmhouse has been meticulously restored and fully modernized, preserving its original character while introducing thoughtful updates, modern systems, and high-quality finishes. A detached structure offers flexible space for a gym or additional accommodations, while the Guest House and Bunk House retain their Vineyard charm, each benefiting from substantial upgrades. A newly constructed garage/barn with lofted storage is discreetly positioned nearby, complementing the functionality of the estate. The property offers both immediate livability and long-term significance. It represents far more than a residence, it is a generational holding defined by land, scale, and irreplaceability. Large, contiguous oceanfront parcels of this caliber are rarely brought to market, particularly in Chilmark, making this a truly one-of-a-kind offering. For those seeking exceptional privacy, scale, and enduring value, this estate stands as one of the most compelling oceanfront opportunities, not only on Martha’s Vineyard, but among coastal properties worldwide.

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, and outdoor shower. Set just beyond, the pool house is designed as a private wellness retreat, featuring a heated indoor pool, spa, sauna, steam room, and cold plunge, all surrounded by retractable walls of glass that seamlessly blend indoor and outdoor living. The first floor also includes a full bath, kitchenette, laundry area, and spacious enclosed porch. The second level offers a luxurious guest suite complete with a bedroom, living room, spa-inspired bath with dual showers and soaking tub, and two private balconies overlooking the pond. The estate also includes an impressive barn-style entertainment pavilion with a professionally designed fitness center featuring floor-to-ceiling windows and scenic pond views. Adjacent is a sprawling recreation lounge designed for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage ideal for luxury vehicles, boating equipment, and recreational storage. Completing the compound are a private tennis court, hilltop writer’s cottage with panoramic water views, and a charming boathouse by the dock for waterfront gear. An unparalleled modern waterfront retreat in one of Martha’s Vineyard’s most exclusive settings.