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$2,200,000
2 Beds 2 Baths 22604013 MLS
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom main house is complemented by a spacious two-bedroom, one-bathroom guest studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. Future expansion to 12 bedrooms is possible with a septic upgrade, although the current system meets all regulations. Enjoy effortless access to Lambert's Cove Beach, 7a Foods, North Tisbury Farm, State Road Restaurant, and all the iconic West Tisbury landmarks.

99 Oak Lane, West Tisbury

$2,200,000
4 Beds 3 Baths 73564420 MLS
This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet of living space. A gunite swimming pool, gardens, expansive lawn areas, outdoor shower, and one-car garage complete the setting. Renovated in 2013 and equipped with central air conditioning, the property feels wonderfully secluded while remaining centrally located for convenient access to both up and down Island destinations. Future expansion to 12 bedrooms is possible with a septic upgrade, although the current system meets all regulations. Enjoy effortless access to Lambert’s Cove Beach, 7a Foods, North Tisbury Farm, State Road Restaurant, and all the iconic West Tisbury landmarks.

99 Oak Lane, West Tisbury

$1,350,000
2 Beds 2 Baths 22604010 MLS
Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings. A generous south-facing living room is filled with natural light and offers peaceful views of the surrounding landscape. The kitchen provides an opportunity to create a space tailored to your vision. Off the kitchen is a large dinning area with a beautiful custom cabinet. The primary suite includes a sitting area and sunroom, while a second bedroom off the front entry features a half bath and access to the outdoor shower. Although the home is currently configured as a two-bedroom residence, it is served by an existing four-bedroom Title V septic system. This property presents an exceptional opportunity for buyers looking to renovate and make a home their own. Heating is provided by a mini-split systems. The expansive outdoor living areas blend seamlessly with the natural surroundings. The house is being sold in as-is condition.

29 Scotchmans Lane, West Tisbury

$1,600,000
4 Beds 3 Baths 22603890 MLS
A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you will find two large bedrooms, a full bathroom with walk-in shower and plenty of attic storage. Set on a picturesque two-acre parcel, the property also features a detached 384-square-foot studio, offering exceptional flexibility. Set back and private from the main house, it is independent and private with its own parking area, yard, and septic system, it presents wonderful possibilities for hosting family and friends or creating a private artist's studio or home office. Ideally located just minutes from Nip 'n Tuck Farm, Up-Island Cronig's Market, Conroy's Apothecary, and Main Street in Vineyard Haven. As a West Tisbury resident, you'll also enjoy access to the coveted Lambert's Cove Beach with a resident permit, one of Martha's Vineyard's most treasured shoreline beaches. *Estate Rules Apply

150 Field View Lane, West Tisbury

$4,125,000
7 Beds 5 Baths 22603630 MLS
An Inspirational Oasis -- Nestled along the gentle slopes of Indian Hill, this secluded three-dwelling compound offers more than three acres of exceptional privacy where rural tranquility meets effortless island living. Centered around a heated saltwater pool, the main house, studio barn, and guest house provide 4,464 square feet of living space surrounded by wildflower meadows, perennial gardens, mature trees, and sweeping lawns. The sun-filled main house features a timeless stone fireplace, inviting living and dining spaces, and a thoughtfully designed kitchen, all oriented toward picturesque garden views. The Studio Barn offers exceptional flexibility for creative pursuits, wellness, guests, or multigenerational living. The two-story Guest House includes three bedrooms, one-and-a-half baths, and a loft-style living area. Together, the property offers seven bedrooms, four-and-a-half baths, and remarkable versatility. Owners enjoy access to Lambert's Cove Beach, Long Point Beach & Wildlife Refuge, nearby farm stands, village amenities, trails, bike paths, and Cedar Tree Neck Sanctuary. Three Dwellings. One Property. Endless Possibilities.

31 Josiah Sachem Way, West Tisbury

$3,600,000
5 Beds 3 Baths 22602483 MLS
Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a patio overlooking the water. The kitchen with casual dining area connects to a screened porch, creating easy indoor-outdoor living. A heated Gunite pool and expansive yard enhance the tranquil setting. Additional features include a first floor bedroom, detached garage, full basement, and a newly installed Title V septic system designed for SIX bedrooms.

20 James Pond Way, West Tisbury

$1,800,000
4 Beds 3 Baths 22602088 MLS
House & Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard perfect for kids and dogs. The yard also encompasses a sweet vegetable garden, a storage shed, and outdoor shower. Inside is open with natural light from windows and skylights. The kitchen flows to the dining area which flows to the living room anchored by a wood stove. Also on this level is the primary BR, and a full BA with soaking tub and separate shower. The loft upstairs offers versatile space for reading, television, or spillover guests. Downstairs on ground level is another full BA, 2 BRS and a light-filled office with exterior access. Other main house features are a new furnace and mini splits for additional heat and air conditioning. LAST BUT NOT LEAST, and adding tremendous value, is a beautiful, spacious 1BR, 1BA year-round guesthouse with central air, a full eat-in kitchen, a gas fireplace in the living room, a bonus attic room, and a deck for bird watching while listening to the distant rhythm of the Atlantic!

188 Vineyard Meadow Farms Road, West Tisbury

$1,225,000
3 Beds 2 Baths 73548242 MLS
Year-round living in the desirable Island Farms Road neighborhood of West Tisbury. This well-built three-bedroom, two-bath home offers a comfortable layout with a first-floor primary bedroom. While ready for your personal updates, it provides a solid foundation to create your forever home. The open kitchen and living area offer a welcoming space for everyday living while the screened porch extends the living area outdoors—perfect for summer dining or simply relaxing in the peaceful surroundings. Mature landscaping, cultivated over many years, creates a private and tranquil setting. Additional amenities include an outdoor shower and garden shed. Ideally located just minutes from Lambert's Cove Beach, the Up-Island Market, bank, pharmacy, garden centers, North Tisbury Farm Market, and State Road Restaurant, this property offers convenient access to many of the Island's favorite destinations and everyday essentials.

52 Oak Knoll, West Tisbury

$3,495,000
4 Beds 4 Baths 73544561 MLS
This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home offices, this residence offers perfect versatility for modern living—whether you require a quiet library or a remote workspace. Step outside onto the welcoming farmer’s porch to take in the beautifully manicured grounds, complete with lush perennial gardens supported by an irrigation system. The backyard serves as a true resort-style retreat, complete with an expansive in-ground pool and a hot tub spa as well as an enclosed outdoor shower. A cobblestone-lined circular driveway leads to ample guest parking and an attached two-bay garage. Combined with a full, versatile basement, this property is a rare find for the discerning buyer. Ideally situated just one mile from Up-Island Cronig's and local conveniences, you are also moments away from Cedar Tree Neck and the private town beauty of Lambert’s Cove Beach. Your sanctuary awaits. $3,495,000.

64 Christiantown, West Tisbury

$1,200,000
73540072 MLS
Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted with mature cedar trees and expansive sky views. With proper permitting, a main house, guest house, and accessory structures may be possible. A carefully crafted building envelope has been established to protect the property's pastoral character and scenic vistas in perpetuity, preserving the timeless appeal of this exceptional parcel. A rare opportunity to create your own private haven in one of West Tisbury's most cherished locations.

23 Onkokemmy Road, West Tisbury

$3,099,000
3 Beds 4 Baths 73539028 MLS
This custom-built Martha’s Vineyard residence blends timeless elegance with contemporary luxury, offering exclusive access to Lambert’s Cove Beach.At its heart is a chef’s kitchen with bespoke cabinetry, honed Carrara marble, Wolf and Sub-Zero appliances, Miele dishwasher, and Hudson Valley lighting. An adjacent custom bar features Dolomite Italian granite, ideal for entertaining.The home boasts refined finishes, including wide-plank heart pine floors, three Rumford fireplaces, a powder room with Durango tile, and a primary bath retreat with Carrara marble and a freestanding soaking tub.Outdoor living is elevated by a mahogany-screened porch with a reclaimed granite hearth, alongside a mahogany-enclosed outdoor shower with Connecticut granite. Additional features include a reverse osmosis water filtration system and a three-bay garage with expansion potential. A rare Vineyard offering combining exceptional craftsmanship and coastal charm.

53 Stoney Hill Rd, West Tisbury

$1,140,000
4 Beds 2 Baths 73533704 MLS
4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the home was designed with quality craftsmanship, natural light, and efficient living in mind. The expansive open living, kitchen, and dining area creates an inviting gathering space, anchored by warm cherry cabinetry, a wood stove, and oversized windows that bring the outdoors in. An atrium addition fills the home with sunlight and offers a tranquil indoor retreat year-round. Eco-conscious features include composting toilets and a greenhouse addition, supporting a more sustainable and self-sufficient lifestyle.

4 Rock Pond Road, West Tisbury

$1,800,000
4 Beds 3 Baths 73504132 MLS
House & Guesthouse near Long Point Beach! The Island's coveted south shore is minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard perfect for kids and dogs. The yard also encompasses a sweet garden, storage shed, and outdoor shower. Inside is open with natural light from windows and skylights. The kitchen flows to the dining area and living room anchored by a wood stove. On this level is the primary BR, and full BA with soaking tub and separate shower. The loft upstairs offers versatile space for reading, television, or spillover guests. Downstairs on ground level is a full BA, 2 BRS and a light-filled office. Other main house features are a new furnace and mini splits for AC. LAST BUT NOT LEAST adding tremendous value is a beautiful, spacious 1BR ADU with AC, gas fireplace, and deck for bird watching while listening to the distant rhythm of the Atlantic!

188 Vineyard Meadow Farms Rd, West Tisbury

$1,575,000
73495787 MLS
Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no existing home can replicate. A naturally flat building envelope crowns the hilltop while the land rolls into a pastoral landscape below. Private without being remote — minutes from Lambert's Cove Beach, West Tisbury village centers, and scenic trails. Architectural plans for a 4-bedroom, 4.5-bath residence & detached garage by Vineyard architect Sullivan & Associates are included. Well installed. Power on-site. Site Plan Review & 6-bedroom Septic Plan approvals in hand. This isn't a compromise. It's everything you wanted, waiting to be built. Very private setting Showing by Appt. only. No DriveBys.

26 Flint Hill Road, West Tisbury

$1,499,000
3 Beds 2 Baths 73493424 MLS
Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen with a center island, and sliding doors that open to a spacious back deck—ideal for outdoor entertaining. The first floor includes a bedroom and a full bathroom, while the second floor offers two large bedrooms and a shared full bathroom. A full-height, dry basement provides excellent storage and potential for future expansion. The landscaped grounds create a picturesque environment, making it a perfect option for year-round living or rental investment.

111 Charles Neck Way, West Tisbury

$7,500,000
5 Beds 7 Baths 73486301 MLS
Nestled within Seven Gates Farm, one of Martha’s Vineyard’s most storied and scenic communities, this 26.5-acre estate features a beautifully renovated farmhouse blending modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property also includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench overlooking Vineyard Sound and the Elizabeth Islands. Located just steps from Gray’s Beach and dock, this is among the most picturesque settings in Seven Gates Farm. The community includes 45 homesites across 1,600 acres, with 1,000 acres of protected conservation land, open fields, woodlands, ponds, and miles of trails. Residents enjoy exclusive access to 1.5 miles of private beach, two piers, and tennis courts. An extraordinary opportunity to be part of a community dedicated to preserving the island’s natural beauty.

85 North Reservoir Road, West Tisbury

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