Chilmark Homes for Sale

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  /12

  $1,125,000

  $450K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  45 Quenames Rd, Chilmark, MA 02535

  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 spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with

  Dawn Bellante Sandpiper Realty, Inc.

  45 Quenames Rd, Chilmark, MA 02535
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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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  /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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  /14

  $1,275,000

  • Land
  • 3.91 Acres
  • $326,087 per Acre

  0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535

  Set amid the rolling farmlands of Chilmark, this beautiful parcel offers an exceptional opportunity to create your own island retreat. Framed by stone walls, wooded surroundings, and open meadow views, the property combines privacy and natural beauty in a serene rural setting with glacial erratics and trails winding throughout. Elevated and peaceful, this is a rare opportunity to build a home

  Meg Bodnar Tea Lane Associates

  0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535
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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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  /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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  /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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  /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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