1,741

Chilmark Homes

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    • 68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      /31

      Est $3,463,448

      Not Listed For Sale

      68 Meeting House Rd, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,300 Sq Ft
      • Built 1990
      68 Meeting House Rd, Chilmark, MA 02535

      Last Sold Summary

      • 88 Days On Market

  • 6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    /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
    • 4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      /75

      Est $3,920,981

      Not Listed For Sale

      4 Tilton Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 1,362 Sq Ft
      • Built 1975
      4 Tilton Rd, Chilmark, MA 02535

      Last Sold Summary

      • 49 Days On Market

  • 15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    /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
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,267,218

      Not Listed For Sale

      7 the Aerie, Chilmark, MA 02535

      • 3 Beds
      • 1.5 Baths
      • 1,386 Sq Ft
      • Built 1989
      7 the Aerie, Chilmark, MA 02535

      Last Sold Summary

      • 11 Days On Market

  • 2 Other House Rd Unit 173, Chilmark, MA 02535
    2 Other House Rd Unit 173, Chilmark, MA 02535
    2 Other House Rd Unit 173, Chilmark, MA 02535
    /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
    • 22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      /17

      Est $2,817,414

      Not Listed For Sale

      22 Tabor Hills, Chilmark, MA 02535

      • 3 Beds
      • 2.5 Baths
      • 2,375 Sq Ft
      • Built 1997
      22 Tabor Hills, Chilmark, MA 02535

      Last Sold Summary

      • 4 Days On Market

  • 205 South Rd, Chilmark, MA 02535
    205 South Rd, Chilmark, MA 02535
    205 South Rd, Chilmark, MA 02535
    /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
    • 24 Blacksmith Valley Rd, Chilmark, MA 02535
      24 Blacksmith Valley Rd, Chilmark, MA 02535
      /2

      Est $5,230,988

      Not Listed For Sale

      24 Blacksmith Valley Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 1,952 Sq Ft
      • Built 1951
      24 Blacksmith Valley Rd, Chilmark, MA 02535

  • 49 Gosnolds Way, Chilmark, MA 02535
    49 Gosnolds Way, Chilmark, MA 02535
    49 Gosnolds Way, Chilmark, MA 02535
    /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
    • 18 Austin Pasture, Chilmark, MA 02535
      18 Austin Pasture, Chilmark, MA 02535
      /2

      Not Listed For Sale

      18 Austin Pasture, Chilmark, MA 02535

      • 5 Beds
      • 4 Baths
      • 5,022 Sq Ft
      • Built 2002
      18 Austin Pasture, Chilmark, MA 02535

  • 16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    /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
    • 26 Pinkletink Rd, Chilmark, MA 02535
      26 Pinkletink Rd, Chilmark, MA 02535
      26 Pinkletink Rd, Chilmark, MA 02535
      /30

      Est $3,891,828

      Not Listed For Sale

      26 Pinkletink Rd, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,748 Sq Ft
      • Built 1979
      26 Pinkletink Rd, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

  • 0, 36, 38 Black Point Rd, Chilmark, MA 02535
    0, 36, 38 Black Point Rd, Chilmark, MA 02535
    0, 36, 38 Black Point Rd, Chilmark, MA 02535
    /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
    • 5 Tree Frog Ln, Chilmark, MA 02535
      5 Tree Frog Ln, Chilmark, MA 02535
      5 Tree Frog Ln, Chilmark, MA 02535
      /25

      Est $2,537,881

      Not Listed For Sale

      5 Tree Frog Ln, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 1,788 Sq Ft
      • Built 1997
      5 Tree Frog Ln, Chilmark, MA 02535

      Last Sold Summary

      • 7 Days On Market

  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /42

    $3,995,000

    • 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
    • 22 Quitsa Ln, Chilmark, MA 02535
      22 Quitsa Ln, Chilmark, MA 02535
      /2

      Not Listed For Sale

      22 Quitsa Ln, Chilmark, MA 02535

      • 5 Beds
      • 5 Baths
      • 3,888 Sq Ft
      • Built 1850
      22 Quitsa Ln, Chilmark, MA 02535

  • 45 Quenames Rd, Chilmark, MA 02535
    45 Quenames Rd, Chilmark, MA 02535
    45 Quenames Rd, Chilmark, MA 02535
    /14

    $1,495,000

    $80K 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 bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility

    Dawn Bellante-Holand Sandpiper Realty

    45 Quenames Rd, Chilmark, MA 02535
    • 2 Creek Hill, Chilmark, MA 02535
      2 Creek Hill, Chilmark, MA 02535
      /2

      Est $1,592,503

      Not Listed For Sale

      2 Creek Hill, Chilmark, MA 02535

      • 2 Beds
      • 1 Bath
      • 770 Sq Ft
      • Built 1920
      2 Creek Hill, Chilmark, MA 02535

  • 61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    /55

    $5,450,000

    • 5 Beds
    • 4 Baths
    • 3,513 Sq Ft

    61 Stonewall Rd, Chilmark, MA 02535

    Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    61 Stonewall Rd, Chilmark, MA 02535
    • 239 State Rd, Chilmark, MA 02535
      239 State Rd, Chilmark, MA 02535
      239 State Rd, Chilmark, MA 02535
      /31

      Est $3,060,207

      Not Listed For Sale

      239 State Rd, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,024 Sq Ft
      • Built 1956
      239 State Rd, Chilmark, MA 02535

      Last Sold Summary

      • 357 Days On Market

  • 100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    /46

    $3,400,000

    • 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
    • 53 Wequobsque Rd, Chilmark, MA 02535
      53 Wequobsque Rd, Chilmark, MA 02535
      /2

      Est $6,283,065

      Not Listed For Sale

      53 Wequobsque Rd, Chilmark, MA 02535

      • 5 Beds
      • 5 Baths
      • 4,240 Sq Ft
      • Built 1997
      53 Wequobsque Rd, Chilmark, MA 02535

  • 6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    /23

    $2,900,000

    $300K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Enjoy the carefree ease of Mid Century Modern architecture in this pristine classic, filled with sunshine and treetop views. Located on a quiet hilltop in Chilmark and offered turn-key furnished, this simple but elegant summer home features four bedrooms, three baths, with original details and design. Its open all-on-one-floor layout with large glass panel doors and windows throughout lead to a

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
    • 51 State Rd, Chilmark, MA 02535
      51 State Rd, Chilmark, MA 02535
      51 State Rd, Chilmark, MA 02535
      /20

      Not Listed For Sale

      51 State Rd, Chilmark, MA 02535

      • 5 Beds
      • 5 Baths
      • 3,200 Sq Ft
      • Built 2017
      51 State Rd, Chilmark, MA 02535

      Last Sold Summary

      • 45 Days On Market

    • 17 High Mark, Chilmark, MA 02535
      17 High Mark, Chilmark, MA 02535
      /2

      Not Listed For Sale

      17 High Mark, Chilmark, MA 02535

      • 7 Beds
      • 5 Baths
      • 3,883 Sq Ft
      • Built 1928
      17 High Mark, Chilmark, MA 02535

    • 76 Menemsha Inn Rd, Chilmark, MA 02535
      76 Menemsha Inn Rd, Chilmark, MA 02535
      76 Menemsha Inn Rd, Chilmark, MA 02535
      /39

      Est $8,129,557

      Not Listed For Sale

      76 Menemsha Inn Rd, Chilmark, MA 02535

      • 3 Beds
      • 5 Baths
      • 4,033 Sq Ft
      • Built 2021
      76 Menemsha Inn Rd, Chilmark, MA 02535

      Last Sold Summary

      • 10 Days On Market

    • 39 Prospect Hill Rd, Chilmark, MA 02535
      39 Prospect Hill Rd, Chilmark, MA 02535
      39 Prospect Hill Rd, Chilmark, MA 02535
      /34

      Est $4,197,952

      Not Listed For Sale

      39 Prospect Hill Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 1980
      39 Prospect Hill Rd, Chilmark, MA 02535

      Last Sold Summary

      • 12 Days On Market

    • 12 Peaked Hill Rd, Chilmark, MA 02535
      12 Peaked Hill Rd, Chilmark, MA 02535
      12 Peaked Hill Rd, Chilmark, MA 02535
      /13

      Est $2,477,601

      Not Listed For Sale

      12 Peaked Hill Rd, Chilmark, MA 02535

      • 4 Beds
      • 1.5 Baths
      • 1,284 Sq Ft
      • Built 1964
      12 Peaked Hill Rd, Chilmark, MA 02535

      Last Sold Summary

      • 28 Days On Market

    • 135 Middle Rd, Chilmark, MA 02535
      135 Middle Rd, Chilmark, MA 02535
      135 Middle Rd, Chilmark, MA 02535
      /7

      Not Listed For Sale

      135 Middle Rd, Chilmark, MA 02535

      • 5 Beds
      • 2 Baths
      • 2,455 Sq Ft
      • Built 1954
      135 Middle Rd, Chilmark, MA 02535

      Last Sold Summary

      • 235 Days On Market

    • 40 Blueberry Ridge Ln, Chilmark, MA 02535
      40 Blueberry Ridge Ln, Chilmark, MA 02535
      /2

      Est $2,359,601

      Not Listed For Sale

      40 Blueberry Ridge Ln, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1981
      40 Blueberry Ridge Ln, Chilmark, MA 02535

    • 45 Beach Rd, Chilmark, MA 02535
      45 Beach Rd, Chilmark, MA 02535
      45 Beach Rd, Chilmark, MA 02535
      /7

      Not Listed For Sale

      45 Beach Rd, Chilmark, MA 02535

      • 6 Beds
      • 6.5 Baths
      • 4,900 Sq Ft
      • Built 1982
      45 Beach Rd, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

    • 86 Harlock Pond Rd, Chilmark, MA 02535
      86 Harlock Pond Rd, Chilmark, MA 02535
      /2

      Est $3,664,757

      Not Listed For Sale

      86 Harlock Pond Rd, Chilmark, MA 02535

      • 5 Beds
      • 4 Baths
      • 3,100 Sq Ft
      • Built 1975
      86 Harlock Pond Rd, Chilmark, MA 02535

    • 86 Menemsha Cross Rd, Chilmark, MA 02535
      86 Menemsha Cross Rd, Chilmark, MA 02535
      86 Menemsha Cross Rd, Chilmark, MA 02535
      /23

      Not Listed For Sale

      86 Menemsha Cross Rd, Chilmark, MA 02535

      • 4 Beds
      • 1 Bath
      • 1,277 Sq Ft
      • Built 1930
      86 Menemsha Cross Rd, Chilmark, MA 02535

      Last Sold Summary

      • 4 Days On Market

    • 31 & 33 Flanders Ln, Chilmark, MA 02535
      31 & 33 Flanders Ln, Chilmark, MA 02535
      31 & 33 Flanders Ln, Chilmark, MA 02535
      /11

      Not Listed For Sale

      31 & 33 Flanders Ln, Chilmark, MA 02535

      • 3 Beds
      • 3 Baths
      • 1,320 Sq Ft
      • Built 1963
      31 & 33 Flanders Ln, Chilmark, MA 02535

      Last Sold Summary

      • 3 Days On Market

    • 0 Menemsha Inn Rd, Chilmark, MA 02535
      0 Menemsha Inn Rd, Chilmark, MA 02535
      0 Menemsha Inn Rd, Chilmark, MA 02535
      /11

      Not Listed For Sale

      0 Menemsha Inn Rd, Chilmark, MA 02535

      0 Menemsha Inn Rd, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

    • 27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535
      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535
      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535
      /21

      Not Listed For Sale

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535

      • 6 Beds
      • 4 Baths
      • 4,967 Sq Ft
      • Built 1978
      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535

      Last Sold Summary

    • 0 Beach Unit 38358, Chilmark, MA 02575
      0 Beach Unit 38358, Chilmark, MA 02575
      0 Beach Unit 38358, Chilmark, MA 02575
      /7

      Not Listed For Sale

      0 Beach Unit 38358, Chilmark, MA 02575

      0 Beach Unit 38358, Chilmark, MA 02575

      Last Sold Summary

      • 12 Days On Market

    • 7 Squibnocket Rd, Chilmark, MA 02535
      7 Squibnocket Rd, Chilmark, MA 02535
      7 Squibnocket Rd, Chilmark, MA 02535
      /16

      Est $4,279,853

      Not Listed For Sale

      7 Squibnocket Rd, Chilmark, MA 02535

      • 6 Beds
      • 4.5 Baths
      • 5,462 Sq Ft
      • Built 1930
      7 Squibnocket Rd, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

    • 139 Old Farm Rd, Chilmark, MA 02535
      139 Old Farm Rd, Chilmark, MA 02535
      139 Old Farm Rd, Chilmark, MA 02535
      /36

      Est $1,081,082

      Not Listed For Sale

      139 Old Farm Rd, Chilmark, MA 02535

      • 3 Beds
      • 3.5 Baths
      • 1,550 Sq Ft
      • Built 2015
      139 Old Farm Rd, Chilmark, MA 02535

      Last Sold Summary

      • 372 Days On Market

Showing Results 121 - 160, Page 4 of 18

Massachusetts Dukes County Marthas Vineyard Chilmark

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