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$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, cabana 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

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$2,999,000
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. Easy expansion is possible with a 5 BR SEPTIC ALREADY IN PLACE! A rare Vineyard offering combining exceptional craftsmanship and coastal charm.

53 Stoney Hill Rd, West Tisbury

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

$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

Listing courtesy of Listing Agent: Patricia Lyman from Listing Office: Compass.

$1,760,000
4 Beds 3 Baths 73504132 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, find an open floor plan with natural light streaming in from windows and skylights. The kitchen flows to the dining area, which flows to the spacious living room anchored by a wood-burning stove for cozy ambience. Also on this level is the primary bedroom with two closets, and a large full bathroom with a soaking tub and separate tiled shower. The larger, open loft upstairs offers versatile living space perfect for reading, television, or spillover guests. Downstairs on ground level is another full bathroom and two bedrooms plus a light-filled home office with a convenient exterior access. Other features for the main house are a new furnace and 4 mini splits for air conditioning. LAST BUT NOT LEAST, adding tremendous value is a beautiful, spacious year-round guesthouse with every detail curated for comfort and style; central air and heat, a living room with a gas fireplace, a full eat-in kitchen, a bedroom with two closets, a full bathroom, a bonus attic room, and a deck perfect for bird watching while listening to the distant rhythm of the Atlantic! This property is not to be missed! Note: At closing Seller will credit Buyer for 4-bedroom septic system upgrade. See design by VLSE in documents.

188 Vineyard Meadow Farms Rd, West Tisbury

Listing courtesy of Listing Agent: Idalyn Macchia Gilstad from Listing Office: Wallace & Co. Sotheby's International Realty.

$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

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..

$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

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

$8,500
3 Beds 2 Baths 73121761 MLS
THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary bedroom has it's own en-suite bathroom, guest share a full bath. Many nice details throughout. There is also a large full basement/game room with Ping Pong table, exercise area and plenty of room for play. The basement exits to outside. Less than a mile to beautiful Lambert's Cove Beach and West Tisbury Center and conservation trails.

29 Bea Lane Wt160 Unit 1, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$11,800
4 Beds 4 Baths 73121597 MLS
THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and updated kitchen with a sunny breakfast nook and banquet. Large living area with television on the lower level as well as a powder room. Upstairs are four large bedrooms, two with high ceilings and private ensuites, one a half bath and the other a full primary suite with shower and luxurious soaking tub overlooking the beautiful private back yard. There is one more shared bath with both tub and shower upstairs. While away your days on the tire swing out back or venture into town to enjoy all the island has to offer such as restaurants, public events, live music, and shopping .

46 Buttonwood Farm Rd W T111 Unit 1, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$14,500
5 Beds 6 Baths 72844763 MLS
THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions adding a base note to the property. Harmonious blending of house and land is reminiscent of English gardens. Truly an exceptional property.Updated bathrooms on the main floor. Renovated master suites. This refined property is located in West Tisbury on the Seven Gates Farm Association offering shared tennis courts (within walking distance), miles of walking trails, several miles of private North Shore beaches, pastoral and picturesque landscapes.

76 School House Lane Wt101, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$38,000
4 Beds 4 Baths 72845499 MLS
THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular drip coffee maker, a Keuring machine, a French press, and a grinder for beans. The open dining and family room have access to a central fireplace. The view from these rooms is amazing and overlooks the pool area. There are four good sized bedrooms. The master is on the first floor with a reading nook, office and adjoining decks. The two upstairs bedrooms in the main house are accessed by a spiral staircase and share a bath. Over the garage is a private living area which with beds, a mini kitchen and full bath.

17 Otis Bassett Rd Wt152, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$3,000
4 Beds 3 Baths 72845445 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large Master bedroom and private bath. The master also has sliding glass doors which lead out to a nice deck with table and chairs. Also downstairs is a cozy bedroom with a trundle bed and a half bath. Adjacent to the indoor/outdoor dining area is the beautifully renovated kitchen with stainless steel appliances and ample cooking amenities. PLEASE NOTE THAT THE ONLY ACCESS TO UPSTAIRS IS VIA AN OPEN SPIRAL STAIRCASE AS PICTURED.

41 Oak Lane Wt147, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$17,600
4 Beds 4 Baths 72844737 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living area upstairs and the bedrooms downstairs, this home is perfect for hosting family and friends or enjoying quiet time on the deck. Its location is perfectly nestled in the woods yet is close to popular Lambert's Cove Beach. PLEASE NOTE THE ONLY ACCESS TO THE LOWER LEVEL BEDROOMS IS VIA AN OPEN SPIRAL STAIRCASE.

40 Summer Circle Wt128, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$8,000
1 Beds 1 Baths 72844885 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a ceiling fan. The living area has a ceiling fan and stays cool with the help of some nearby trees providing shade. Inside, enjoy all the comforts of home. Outside, explore Seth's Pond on a paddle board or kayak. Lambert's Cove, the expansive white-sand beach is only .3 of a mile away and offers swimming, sunbathing and picnicking. Perfect place for a family to enjoy the entire summer.

10 James Pond Way Wt133, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$12,000
3 Beds 1 Baths 72844862 MLS
Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with bathtub and shower. There is also an enclosed outdoor shower. The two bedrooms with queen beds each have an A/C unit as does the living and dining area.This country home sits close to Black Water Pond and a small cranberry pond, in a spot with easy access to the Land Bank walking trails. You'll also be just three miles inland of Vineyard Haven, the picturesque port town where the ferry from the mainland docks. NO USE OF FIREPLACE UNLESS GIVEN WRITTEN PERMISSION. NO FENCE IN YARD, POND NEARBY. SUV, JEEP or similar vehicle recommended for bumpy road.

76 Ben Chase Rd Wt136, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$30,000
5 Beds 4 Baths 72844834 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself to congregating with the family or having room to spread out. A beautifully landscaped yard and patio allow for quiet relaxing with expansive summer living space! Very close to Lambert's Cove Beach, local farm stands, restaurants, and West Tisbury Village. Ideal for family reunions and special events.

37 Sachem Circle Wt129, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$17,600
4 Beds 4 Baths 72844916 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living area upstairs and the bedrooms downstairs, this home is perfect for hosting family and friends or enjoying quiet time on the deck. Its location is perfectly nestled in the woods yet is close to popular Lambert's Cove Beach. PLEASE NOTE THE ONLY ACCESS TO THE LOWER LEVEL BEDROOMS IS VIA AN OPEN SPIRAL STAIRCASE.

40 Summer Circle Wt128, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$50,000
4 Beds 3 Baths 72844878 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom. Open living dining area. Small but functional galley kitchen. The glassed-in breezeway offers comfortable wicker furniture to relax in while reading and looking at the gardens. The cottage, attached to the breezeway, is a family great room with plasma TV, Internet access, game table area, studio kitchen: and a bathroom with Jacuzzi tub and steam generator glass shower. A boardwalk leads you to a hot tub with a table surround to use for lunch. Nearby is a hot/cold shower.

29 Naushon Rd Wt142, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$19,000
6 Beds 7 Baths 72952014 MLS
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the beautiful South shore of the Island and then come home to relax and unwind in the hot tub overlooking the pond, and cozy up near the stunning outdoor fireplace. This amazing home boasts 5 bedrooms all with en-suite full bathrooms in the main house, and a guest house with 1 bedroom with a full bathroom. 3 outdoor showers, hot tub, rooftop deck overlooking your private pond, entertainment room, play room for kids and a full gym. Come and stay in this meticulously maintained luxury home for a vacation to remember!

40 Sweet William Way Wt155, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$18,000
3 Beds 3 Baths 72845474 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short distance to the private beach. Inside the house you will find new appliances in the kitchen area. The house has central air to enjoy, but maybe the ocean breezes might be enough. If you are looking for a wonderful Vineyard Experience, this is the house for you!Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. I

71 Bartmus Luce Road Wt154, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$46,000
6 Beds 5 Baths 72854118 MLS
THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin bed. Laundry room is on the main level as well. Up stairs you will find two master suites both with King beds. The third bedroom has two twins and the fourth bedroom has a queen. The 3rd and 4th bedrooms share a full bathroom at the end of the hall. In additional to the abundant living and outdoor space is a finished lower level complete with pool and foosball table. The lower level has a full bathroom, kitchen, living area with stove, bedroom with a queen, and separate entrance.The finishing touch is a lovely heated pool with large deck, mature plantings, and sweeping views of the pasture.

99 Pond Road Wt104, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$4,800
3 Beds 3 Baths 73007853 MLS
THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech groves. The 2-story, impeccably maintained 3500 square foot home has a flavoring of the original Vineyard. The first floor offers an open living room, an open fully-equipped kitchen, a dining area that seats 6, a full bathroom, and a separate office for quiet privacy. Upstairs, there are three bedrooms, including a primary bedroom suite. There is also a sitting area/library and full bathroom.

165 Christiantown Rd Wt157, West Tisbury

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

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