Chilmark, MA Houses for Sale

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  /38

  $3,795,000

  $400K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,426 Sq Ft

  96 Hammett Ln, Chilmark, MA 02535

  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

  Brenda Galligan Karen M. Overtoom R.E.

  96 Hammett Ln, Chilmark, MA 02535
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  /32

  $5,200,000

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft

  49 Gosnolds Way, Chilmark, MA 02535

  Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  49 Gosnolds Way, Chilmark, MA 02535
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  /28

  $1,289,000

  $110K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,996 Sq Ft

  29 Scotchmans Ln, Vineyard Haven, MA 02568

  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 offer exciting possibilities for artists,

  Diana Gilmore Island Real Estate

  29 Scotchmans Ln, Vineyard Haven, MA 02568
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  /30

  $2,395,000

  $105K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft

  16 South Rd, Chilmark, MA 02535

  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

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
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  /34

  $1,600,000

  • 3 Beds
  • 3 Baths
  • 2,155 Sq Ft

  132 South Rd, Chilmark, MA 02535

  Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the

  Lisa Da Silva Compass

  132 South Rd, Chilmark, MA 02535
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  /21

  $1,499,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  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

  Emma Kennedy Sandpiper Realty, Inc.

  111 Charles Neck Way, Vineyard Haven, MA 02568
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  /39

  $16,000,000

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  0, 36, 38 Black Point Rd, Chilmark, MA 02535

  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

  Abby Rabinovitz Tea Lane Associates

  0, 36, 38 Black Point Rd, Chilmark, MA 02535
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  /25

  $2,375,000

  $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,500 Sq Ft

  14 Ephriam Allen Rd, West Tisbury, MA 02568

  Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevation and enjoys views of its small kettle pond, winter waterviews and the Sanctuary. There's also a

  Michelle Kelly Tea Lane Associates

  14 Ephriam Allen Rd, West Tisbury, MA 02568
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  /25

  $6,500,000

  • 6 Beds
  • 7 Baths
  • 4,753 Sq Ft

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568

  Private West Tisbury Oasis – Modern Luxury on 4.85 AcresBuilt by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional

  Joe & Nicole Holland Vineyard Dream Realty LLC

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568
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  /25

  $1,795,000

  • 4 Beds
  • 1.5 Baths
  • 1,871 Sq Ft

  487 Lamberts Cove Rd, Vineyard Haven, MA 02568

  This sweet four-bedroom home has fantastic energy and captures the effortless feeling of summer on Martha’s Vineyard. Set high on 2.4 acres along beloved Lamberts Cove Road, the property is just a short walk to Ice House, Lamberts Cove Beach, and Seth’s Pond. Designed for easy enjoyment, the home offers a warm and welcoming kitchen filled with sunshine, a spacious living room, and two fireplaces

  Jill Napior Tea Lane Associates

  487 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /37

  $3,795,000

  • 3 Beds
  • 4 Baths
  • 3,426 Sq Ft

  96 Hammett Ln, Chilmark, MA 02535

  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

  Brenda Galligan Karen M. Overtoom R.E.

  96 Hammett Ln, Chilmark, MA 02535
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  /70

  $3,790,000

  $860K PRICE DROP

  • 7 Beds
  • 4.5 Baths
  • 3,312 Sq Ft

  31 Josiah Sachem Way, Vineyard Haven, MA 02568

  THE COMPOUND AT INDIAN HILLSome properties are a house. This one is a world.Set on more than three private acres along the gentle slopes of Indian Hill, this is a true multi-dwelling compound, purpose-built for the way people actually want to live now: together, apart, and on their own terms. A main house, a studio barn, and a guest house share 4,464 square feet of living space across the

  Helena Kirschenbaum Studio Realty

  31 Josiah Sachem Way, Vineyard Haven, MA 02568
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  /51

  $2,999,000

  $300K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,082 Sq Ft

  53 Stoney Hill Rd, Vineyard Haven, MA 02568

  Nestled in one of Martha’s Vineyard’s most coveted locations, this custom-built residence blends timeless elegance with contemporary luxury. Complete with exclusive access to the serene shores of Lambert’s Cove Beach.At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, a handmade subway tile backsplash, Wolf

  Jennifer DaSilva Compass | Point B

  53 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /20

  $1,525,000

  $75K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,334 Sq Ft

  150 Field View Ln, Vineyard Haven, MA 02568

  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

  Sheila Morse Island Real Estate

  150 Field View Ln, Vineyard Haven, MA 02568
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  /42

  $7,500,000

  $1M PRICE DROP

  • 5 Beds
  • 7 Baths
  • 4,531 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  /44

  $4,300,000

  $500K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  Two homes on over three acres of waterfront on the beautiful and coveted Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two existing homes and a private permitted dock.Both the main house and guest house boast unobstructed water views, creating a tranquil and picturesque setting perfect for birdwatching, relaxation, and

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /37

  $11,400,000

  • 4 Beds
  • 3.5 Baths
  • 2,480 Sq Ft

  104 Old Herring Creek Rd, Vineyard Haven, MA 02568

  An extraordinary opportunity to own one of the Cape’s most distinctive waterfront properties, this exceptional 5.3-acre estate parcel combines remarkable natural beauty, complete privacy, and an unparalleled coastal setting. At its heart is a beautifully renovated four-bedroom beach cottage, thoughtfully updated with modern amenities while preserving the character and intimacy of a classic

  Thomas Leclair Landvest MV

  104 Old Herring Creek Rd, Vineyard Haven, MA 02568
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  /49

  $9,750,000

  • 7 Beds
  • 5 Baths
  • 3,617 Sq Ft

  23 Flanders Ln, Chilmark, MA 02535

  A rare offering of land, history, and sweeping water views — this exceptional 8.7+/- acre estate commands panoramic views of Menemsha Pond and Vineyard Sound from its rolling lawns and open meadows. Property includes parking and access to Menemsha Pond.Whether you're drawn by the storied architecture, the expansive land, or the irreplaceable Vineyard Sound vistas, this is a compound that

  Julianna Flanders Flanders Real Estate

  23 Flanders Ln, Chilmark, MA 02535
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  /46

  $3,300,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,383 Sq Ft

  100 Gosnolds Way, Chilmark, MA 02535

  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

  Julianna Flanders Flanders Real Estate

  100 Gosnolds Way, Chilmark, MA 02535
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  /11

  $2,495,000

  $455K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,506 Sq Ft

  24 Cournoyer Rd, Vineyard Haven, MA 02568

  This mixed use building is zoned for residential and commercial use. It is extremely well built with an emphasis on non-toxic materials throughout. High ceilings on all three levels. There are radiant floors mixed with forced hot air/AC. The building offers a variety of uses for a new owner. The existing spaces are very versatile and would be ideal for any service oriented business given the

  Jill Napior Tea Lane Associates

  24 Cournoyer Rd, Vineyard Haven, MA 02568
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  /46

  $3,900,000

  • 3 Beds
  • 4 Baths
  • 2,960 Sq Ft

  3 Bens Way, Chilmark, MA 02535

  Sited on 3.94 acres in the North Tabor Farm subdivision, this flexible 3-4 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and

  Russell Maloney Russell Maloney Real Estate

  3 Bens Way, Chilmark, MA 02535

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