Just 7 miles off the southern coast of Cape Cod. Remember the movie JAWS ? The 6 island towns are Oak Bluffs, Edgartown, Vineyard Haven, West Tisbury, Chilmark, Aquinnah. Oak Bluffs is most well known for its gingerbread cottages, open harbor, and its vibrant town along busy Circuit Avenue. Oak Bluffs enjoys a reputation as one of the more active night-life towns on the island. Oak Bluffs also includes the East Chop peninsula, Lagoon Heights and Harthaven. Edgartown, which includes Chappaquiddick Island and Katama. Edgartown is noted for its rich whaling tradition, and is the island's largest town by population and area. Vineyard Haven is the main village in Tisbury, and includes the West Chop peninsula. It is the island's primary port of entry for people and cargo, supplemented by the seasonal port in Oak Bluffs. West Tisbury is the island's agricultural center, and hosts the well known Martha's Vineyard Agricultural Fair each year. Chilmark, including the fishing village of Menemsha & Coast Guard Station. Chilmark has remained rural and features the island's hilliest terrain. Aquinnah, formerly Gay Head, is home to the Wampanoag Indian tribe, beautiful clay cliffs and quiet natural serenity.

 

 

$2,678,000
4 Beds ⋅ 4 Baths ⋅ 22604054 MLS
Due to ongoing construction, the property may pose safety risks. Entry is at your own risk, and access is permitted only when accompanied by a licensed real estate agent. The agent of the buyer must be present at all buyer-client showings, inspections, and walkthroughs unless otherwise agreed to in advance by the listing agent.

31 Temahigan Avenue, Oak Bluffs
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 73565263 MLS
Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and entertaining. The kitchen overlooks the dining area, an intimate sitting area, and a versatile game and reading area beyond. The spacious TV and family room features custom built-in bookcases and French doors that open onto a bluestone patio and the pool area beyond. A generous screened porch provides additional living space. Completing the first floor is a large guest bedroom with an ensuite bath, along with a powder room, pantry, mudroom, and laundry room. Upstairs, the gracious primary suite features vaulted ceilings, a sitting area, and a luxurious bath with a soaking tub. There are two additional guest bedrooms, each with an ensuite bath. A private sun deck overlooks the pool and beautifully landscaped grounds, offering a wonderful spot to relax and enjoy distant water views. A dedicated office with water views toward Woods Hole and the Elizabeth Islands provides an inspiring setting for work or quiet retreat. Above the garage, a separate one-bedroom apartment offers a full kitchen, bath, and laundry, with convenient interior and exterior access. The living space in the apartment is currently being used as the sixth bedroom. Outside, the property transforms into a private oasis. The upper garden patio features an inviting sofa seating, while a stone staircase leads down to the heated 20' x 40' pool with spa. The expansive pool terrace is furnished with comfortable loungers and the pool cabana provides additional seating and a welcome retreat from the sun, all surrounded by lush, mature plantings. Other amenities include a gym, two enclosed outside showers and a pool powder room. With its exceptional privacy, generous living spaces, water views, pool and cabana, guest accommodations, this stunning property is truly one of the Grand Dames of West Chop.

59 Hagerty Drive, Tisbury
$2,850,000
6 Beds ⋅ 1 Baths ⋅ 22604053 MLS
Two side by side cottages built in 1945 Directly Pondfront on Sengekontacket with 180 degree views over the pond out to the Causeway, State Beach, Nantucket Sound and beyond.

49 The Boulevard, Edgartown
$3,650,000
73565039 MLS
Set in the heart of Katama, this exceptional 5.5-acre building lot offers a rare opportunity to create a private island retreat surrounded by nature and conservation land. The property is bordered by 87 acres of Sheriffs Meadow conservation land and an additional 75 acres of town-owned land, providing an extraordinary sense of privacy and protected open space. Located in a well-established Katama neighborhood, the property captures the essence of the island lifestyle, with the sights, sounds, and salt air of the Atlantic Ocean close by. Just minutes from South Beach and Wilson’s Landing, easily enjoy swimming, boating, fishing, and long summer days by the water. A remarkable opportunity to build in one of the Vineyard’s most coveted settings, with expansive protected land and the beauty of Katama all around.

8 Turkeyland Cove Road, Edgartown
$4,725,000
3 Beds ⋅ 5 Baths ⋅ 73564664 MLS
Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home’s comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist’s dream, overlooking the pool and offering a versatile space for creative pursuits, hobbies, or use as a pool cabana.

149 Litchfield Road, Edgartown
$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
$2,995,000
4 Beds ⋅ 2 Baths ⋅ 22604007 MLS
WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock.

27 Beach Road, Oak Bluffs
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 73564299 MLS
Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

9 Codman Spring Road, Edgartown
$1,895,000
3 Beds ⋅ 2 Baths ⋅ 22603999 MLS
Rarely does such a unique, waterfront location become available. With amazing, 180+ degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the tranquil feel and the cooling shade trees will make you forget that you are still so close to town and ferry. The property is hugged by the Lagoon on one side and Vineyard Haven Harbor across the street on the other. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private water access, is a year-round home with breathtaking, expansive views up and across the lagoon. The upper level has a spacious deck overlooking the gardens and sweeping views of the lagoon. The waterside patio has beautiful perennial gardens. A canopy of mature shade trees keeps the property cool. Enjoy meals al fresco in the shade while enjoying the water views. There are many creative details throughout. The sellers have been actively making improvements to increase the commercial usage. Soon the be an art gallery, the commercial building is currently used as an artist's studio. Built with SIPS construction, this building is energy efficient and wind resistant. Property is connected to the town sewer and town water. Please note: This property is being sold "as is". Buyer is responsible for completing the necessary due diligence with the town and an engineer about this unique property that offers a plethora of opportunities.

129 Beach Road, Tisbury
$3,875,000
5 Baths ⋅ 73564126 MLS
EXCEPTIONAL MIXED-USE INVESTMENT AND OWNER-OCCUPANT OPPORTUNITY JUST MINUTES FROM HISTORIC EDGARTOWN ON BEAUTIFUL MARTHA'S VINEYARD! This meticulously maintained 6,712 SF property offers three commercial units plus a residential apartment with an additional side attic future expansion potential to add an additional apartment. Commercial spaces include a dental practice with finished lower level (full bath, kitchenette, living area & bedroom, and storage room), a Pilates studio with reception area, two studios & half bath, and a commercial catering kitchen with a full basement prep/expansion kitchen and half bath. The spacious 1+ bedroom condo features open-concept living, kitchen, bonus room (area with built in couch/bed) & full bath. Unfinished attic includes architectural plans for a second residential apartment - enhancing future value and income potential. Ideal for medical, dental, restaurant, wellness, professional offices, retail, creative studios or investors. Property has town water and sewer - a great bonus. Ample on-site parking, flexible layout, and an outstanding Edgartown location just outside the Historic District.

258 Edgartown-Vineyard Haven Rd, Edgartown
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