4,264

Chilmark, MA Homes

Section Image
    • /12

      Est $2,452,473

      Not Listed For Sale

      5 Ocean View Farm Rd, Chilmark, MA 02535

      • 3 Beds
      • 1.5 Baths
      • 1,342 Sq Ft
      • Built 1971
      5 Ocean View Farm Rd, Chilmark, MA 02535

      Last Sold Summary

      • 3 Days On Market

  • /26

    $2,495,000

    • 3 Beds
    • 2 Baths
    • 2,510 Sq Ft

    26 Bijahs Way, Chilmark, MA 02535

    This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern

    Brenda Galligan Karen M. Overtoom R.E.

    26 Bijahs Way, Chilmark, MA 02535
  • /2

    $400,000

    Sold Aug 13, 2025

    40 Wampeche Rd Unit R, West Tisbury, MA 02568

    • Land
    • 3 Acres
    • $133,333 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    40 Wampeche Rd Unit R, West Tisbury, MA 02568
    • /2

      Est $2,771,760

      Not Listed For Sale

      27 Ocean View Farm Rd, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,450 Sq Ft
      • Built 1964
      27 Ocean View Farm Rd, Chilmark, MA 02535

  • /28

    $22,950,000

    • 7 Beds
    • 8.5 Baths
    • 8,200 Sq Ft

    60 Bartimus Luce Rd, Vineyard Haven, MA 02568

    This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design,

    Gerrett Conover Landvest MV

    60 Bartimus Luce Rd, Vineyard Haven, MA 02568
  • /27

    $1,400,000

    Sold Dec 18, 2025

    42 Hidden Village Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,702 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $823/SF
    • 60 Days On Market

    Current Estimated Value $1,453,855

    Last Listing Agent Sheila Morse Island Real Estate

    42 Hidden Village Rd, Vineyard Haven, MA 02568
    • /69

      Est $2,495,590

      Not Listed For Sale

      276 South Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 2,034 Sq Ft
      • Built 1981
      276 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 122 Days On Market

  • /39

    $3,395,000

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

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • /34

    $2,175,000

    Sold Oct 10, 2025

    24 Alex Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 2,879 Sq Ft
    • Built 1985

    Last Sold Summary

    • 13% Below List Price
    • $755/SF
    • 89 Days On Market

    Current Estimated Value $2,316,835

    Last Listing Agent Elissa Lash Tea Lane Associates

    24 Alex Way, Vineyard Haven, MA 02568
    • /37

      Est $2,222,524

      Not Listed For Sale

      2 Rockrose Path, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 1,900 Sq Ft
      • Built 1978
      2 Rockrose Path, Chilmark, MA 02535

      Last Sold Summary

      • 414 Days On Market

  • /51

    $9,875,000

    • 6 Beds
    • 5.5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist’s studio, and a detached garage with an additional bedroom above — creating the ideal retreat for extended

    Jill Napior Tea Lane Associates

    6 Wakeman Rd, Chilmark, MA 02535
  • /16

    $475,000

    Sold Oct 20, 2025

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 7% Above List Price
    • 11 Days On Market

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    • /20

      Est $2,915,065

      Not Listed For Sale

      23 Black Point Rd, Chilmark, MA 02535

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft
      • Built 2004
      23 Black Point Rd, Chilmark, MA 02535

      Last Sold Summary

      • 13 Days On Market

  • /11

    $1,250,000

    • Land
    • 1.9 Acres
    • $657,895 per Acre

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535

    Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit!Surrounded by ancient stone walls on three sides and mature trees, the land has stunning sunset skies, lovely pastoral

    Jill Napior Tea Lane Associates

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
  • /27

    $1,875,000

    Sold Aug 27, 2025

    212 Charles Neck Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $1,085/SF
    • 71 Days On Market

    Current Estimated Value $1,769,347

    Last Listing Agent Perry Patterson MV Luxury Homes LLC

    212 Charles Neck Way, Vineyard Haven, MA 02568
    • /21

      Not Listed For Sale

      3 Pepperbush Ln, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 2,686 Sq Ft
      • Built 1977
      3 Pepperbush Ln, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

  • /9

    $1,200,000

    • Land
    • 3.42 Acres
    • $350,877 per Acre

    23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557

    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

    Katherine Donahue Sandpiper Realty

    23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557
  • /12

    $1,075,000

    Sold Dec 18, 2025

    1 Crowberry Ln Unit 19, Chilmark, MA 02535

    • Land
    • 4.32 Acres
    • $248,843 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 22 Days On Market

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    1 Crowberry Ln Unit 19, Chilmark, MA 02535
    • /69

      Est $3,183,104

      Not Listed For Sale

      300 North Rd, Chilmark, MA 02535

      • 2 Beds
      • 3 Baths
      • 2,515 Sq Ft
      • Built 1995
      300 North Rd, Chilmark, MA 02535

      Last Sold Summary

      • 193 Days On Market

  • /7

    $2,500,000

    • Land
    • 1.4 Acres
    • $1,785,714 per Acre

    2 Other House Rd Unit 173, Chilmark, MA 02535

    Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

    Russell Maloney Russell Maloney Real Estate

    2 Other House Rd Unit 173, Chilmark, MA 02535
  • /6

    $430,000

    Sold Jun 30, 2025

    0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535

    • Land
    • 1.4 Acres
    • $307,143 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535
    • /29

      Est $2,331,715

      Not Listed For Sale

      50 South Rd, Chilmark, MA 02535

      • 5 Beds
      • 3 Baths
      • 2,427 Sq Ft
      • Built 1729
      50 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 111 Days On Market

  • /41

    $5,350,000

    Open Sat 11:30AM - 1:30PM $300K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,402 Sq Ft

    205 South Rd, Chilmark, MA 02535

    CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a

    Tina Miller Donnelly + Co.

    205 South Rd, Chilmark, MA 02535
  • /30

    $3,375,000

    Sold Sep 26, 2025

    179 Tisbury Ln E, West Tisbury, MA 02575

    • 4 Beds
    • 2 Baths
    • 2,813 Sq Ft
    • Built 1982

    Last Sold Summary

    • 13% Below List Price
    • $1,200/SF
    • 73 Days On Market

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    179 Tisbury Ln E, West Tisbury, MA 02575
    • /24

      Est $2,467,657

      Not Listed For Sale

      99 Hammett Rd, Chilmark, MA 02535

      • 4 Beds
      • 5.5 Baths
      • 2,405 Sq Ft
      • Built 2007
      99 Hammett Rd, Chilmark, MA 02535

      Last Sold Summary

      • 10 Days On Market

  • /36

    $1,390,000

    $105K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 1,564 Sq Ft

    40 Scotchmans Ln, Vineyard Haven, MA 02568

    A Home with history, built in the early 1800's this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

    James Osmundsen Donnelly + Co

    40 Scotchmans Ln, Vineyard Haven, MA 02568
  • /59

    $2,225,000

    Sold Jun 10, 2026

    157 Ben Chase Rd, West Tisbury, MA 02575

    • 4 Beds
    • 2.5 Baths
    • 2,983 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $746/SF
    • 465 Days On Market

    Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

    157 Ben Chase Rd, West Tisbury, MA 02575
    • /48

      Not Listed For Sale

      49 Tilton Rd, Chilmark, MA 02535

      • 6 Beds
      • 5 Baths
      • 3,834 Sq Ft
      • Built 1995
      49 Tilton Rd, Chilmark, MA 02535

      Last Sold Summary

      • 48 Days On Market

  • /37

    $3,600,000

    • 5 Beds
    • 3 Baths
    • 2,791 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    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

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
    • /6

      Not Listed For Sale

      0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

      0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

  • /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
    • /20

      Not Listed For Sale

      168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

      168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /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
    • /7

      Not Listed For Sale

      419 Lamberts Cove Rd, West Tisbury, MA 02568

      419 Lamberts Cove Rd, West Tisbury, MA 02568

      Last Sold Summary

      • 2 Days On Market

  • /33

    $1,600,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    1 Red Arrow Rd, Vineyard Haven, MA 02568

    South Mountain designed and built, energy efficient home that takes excellent advantage of the 3-acre parcel's southerly orientation with both passive solar gain and solar panels. The sun-lit great room combines living room, dining and kitchen and opens out onto the lovely screened porch and patio beyond. The original 3-bedroom home was thoughtfully expanded by buiding out finished space in the

    Candy DaRosa Feiner Real Estate

    1 Red Arrow Rd, Vineyard Haven, MA 02568
    • /3

      Not Listed For Sale

      25 Plum Bush Point Rd, West Tisbury, MA 02568

      25 Plum Bush Point Rd, West Tisbury, MA 02568

      Last Sold Summary

      • 15 Days On Market

  • /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
    • /32

      Est $3,096,760

      Not Listed For Sale

      4 Bartlett Woods, Chilmark, MA 02535

      • 4 Beds
      • 3.5 Baths
      • 3,500 Sq Ft
      • Built 2023
      4 Bartlett Woods, Chilmark, MA 02535

      Last Sold Summary

      • 194 Days On Market

  • /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
    • /31

      Not Listed For Sale

      8 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

      • 3 Beds
      • 3 Baths
      • 4,591 Sq Ft
      • Built 1981
      8 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

      Last Sold Summary

      • 18 Days On Market

Showing Results 201 - 240, Page 6 of 18

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