1,730

Chilmark Homes

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    • /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

      • $1,995/SF
      • 48 Days On Market
      • Last Sold Price $7,650,000
      • Nov 21, 2024

      Last Listing Agent Robert Kenney Tea Lane Associates

  • /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
  • /24

    $4,325,000 Sold Dec 05, 2025

    18 Homeward Way, Chilmark, MA 02535

    • 5 Beds
    • 2.5 Baths
    • 3,885 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $1,113/SF
    • 8 Days On Market

    Current Estimated Value $4,550,558

    Last Listing Agent Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
    • /32

      Est $3,006,835 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

      • $857/SF
      • 194 Days On Market
      • Last Sold Price $3,000,000
      • Jan 09, 2025

      Last Listing Agent Kathryn Tate Kathryn Tate Gothard

  • /8

    $1,575,000

    • 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
  • /37

    $4,350,000 Sold Jan 07, 2026

    146 Quansoo Rd, Chilmark, MA 02535

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft
    • Built 1988

    Last Sold Summary

    • 21% Below List Price
    • $1,265/SF
    • 155 Days On Market

    Current Estimated Value $4,333,864

    Last Listing Agent Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
    • /14

      Not Listed For Sale

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535

      Last Sold Summary

      • 145 Days On Market
      • Last Sold Price $2,900,000
      • Jan 24, 2024

      Last Listing Agent Jeffrey DuBard Byrne & Company Real Estate

  • /39

    $12,500,000

    • 5 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    18 Spruce Gate Rd, Chilmark, MA 02535

    Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm—a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

    Alyssa Halisky Wallace & Co. Sotheby's

    18 Spruce Gate Rd, Chilmark, MA 02535
  • /17

    $1,790,000 Sold Sep 23, 2025

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

    • Land
    • 3.3 Acres
    • $542,424 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 77 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    • /13

      Not Listed For Sale

      70 State Rd, Aquinnah, MA 02535

      • 1 Bed
      • 1 Bath
      • 816 Sq Ft
      • Built 1920
      70 State Rd, Aquinnah, MA 02535

      Last Sold Summary

      • $1,287/SF
      • 25 Days On Market
      • Last Sold Price $1,050,000
      • Jun 14, 2023

      Last Listing Agent Jim Feiner Feiner Real Estate

  • /30

    $2,475,000

    • 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
  • /3

    $3,100,000 Sold Jul 03, 2025

    10 Basin Rd, Chilmark, MA 02535

    • 6 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • Built 1975

    Last Sold Summary

    • $2,067/SF

    Current Estimated Value $3,030,376

    Last Listing Agent Julianna Flanders Flanders Real Estate

    10 Basin Rd, Chilmark, MA 02535
    • /6

      Not Listed For Sale

      0 Beach Lot Quansoo #136, Chilmark, MA 02535

      0 Beach Lot Quansoo #136, Chilmark, MA 02535

      Last Sold Summary

      • 29 Days On Market
      • Last Sold Price $430,000
      • Apr 30, 2024

      Last Listing Agent June Flake Viewpoints

  • /40

    $7,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535
  • /28

    $2,550,000 Sold Oct 02, 2025

    10 Mollys Way, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft
    • Built 1926

    Last Sold Summary

    • 14% Below List Price
    • $1,673/SF
    • 130 Days On Market

    Current Estimated Value $2,466,710

    Last Listing Agent Peyton Wallace Studio Realty

    10 Mollys Way, Chilmark, MA 02535
    • /13

      Not Listed For Sale

      0 Gosnold's Way, Chilmark, MA 02535

      0 Gosnold's Way, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market
      • Last Sold Price $10,500,000
      • Oct 02, 2023

      Last Listing Agent Deb Hancock Hancock Real Estate

  • /3

    $1,325,000

    • Land
    • 4.28 Acres
    • $309,579 per Acre

    0/15 N Way, Chilmark, MA 02535

    Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of

    Stacy Ickes Donnelly + Co.

    0/15 N Way, Chilmark, MA 02535
  • /2

    $5,900,000 Sold Oct 31, 2025

    12 Squibnocket Rd, Chilmark, MA 02535

    • 6 Beds
    • 4.5 Baths
    • 3,143 Sq Ft
    • Built 1849

    Last Sold Summary

    • $1,877/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    12 Squibnocket Rd, Chilmark, MA 02535
    • /6

      Not Listed For Sale

      0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535

      0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market
      • Last Sold Price $430,000
      • Oct 10, 2024

      Last Listing Agent LINK Email Cache LINK

  • /6

    $430,000 Sold Jun 18, 2025

    0 Quansoo Beach Lot Unit 48 43485, 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 48 43485, Chilmark, MA 02535
    • /3

      Not Listed For Sale

      0 Black Point Road Beach Lot 7, Chilmark, MA 02535

      0 Black Point Road Beach Lot 7, Chilmark, MA 02535

      Last Sold Summary

      • 1 Day On Market
      • Last Sold Price $435,000
      • Nov 20, 2023

      Last Listing Agent Meg Bodnar Tea Lane Associates

  • /39

    $2,225,000 Sold Oct 24, 2025

    9 Beetlebung Grove Way, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,968 Sq Ft
    • Built 1994

    Last Sold Summary

    • 11% Below List Price
    • $750/SF
    • 98 Days On Market

    Current Estimated Value $2,293,578

    Last Listing Agent Stephanie Roache Donnelly + Co.

    9 Beetlebung Grove Way, Chilmark, MA 02535
    • /29

      Est $1,983,307 Not Listed For Sale

      5 Oyster Ln, Chilmark, MA 02535

      • 2 Beds
      • 1 Bath
      • 1,108 Sq Ft
      • Built 1994
      5 Oyster Ln, Chilmark, MA 02535

      Last Sold Summary

      • 5% Above List Price
      • $1,710/SF
      • 44 Days On Market
      • Last Sold Price $1,895,000
      • Sep 06, 2024

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

  • /2

    $440,000 Sold Sep 22, 2025

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    • /17

      Est $1,964,647 Not Listed For Sale

      15 Marsh Rd, Chilmark, MA 02535

      • 2 Beds
      • 1.5 Baths
      • 800 Sq Ft
      • Built 1954
      15 Marsh Rd, Chilmark, MA 02535

      Last Sold Summary

      • 6% Above List Price
      • $2,312/SF
      • 9 Days On Market
      • Last Sold Price $1,850,000
      • Dec 20, 2023

      Last Listing Agent Jim Feiner Feiner Real Estate

  • /37

    $6,550,000 Sold Nov 14, 2025

    20 Eliot Ave, Chilmark, MA 02535

    • 4 Beds
    • 3.5 Baths
    • 3,355 Sq Ft
    • Built 1993

    Last Sold Summary

    • 1% Below List Price
    • $1,952/SF
    • 46 Days On Market

    Current Estimated Value $6,510,692

    Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

    20 Eliot Ave, Chilmark, MA 02535
    • /22

      Est $1,692,216 Not Listed For Sale

      5 Meetinghouse Rd, Chilmark, MA 02535

      • 3 Beds
      • 2.5 Baths
      • 1,008 Sq Ft
      • Built 2010
      5 Meetinghouse Rd, Chilmark, MA 02535

      Last Sold Summary

      • 13% Above List Price
      • $1,488/SF
      • 351 Days On Market
      • Last Sold Price $1,500,000
      • Nov 05, 2024

      Last Listing Agent Tina Miller Donnelly + Co.

  • /32

    $1,050,000 Sold May 29, 2025

    10 Rumpus Ridge Rd, Chilmark, MA 02535

    • 4 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • Built 1960

    Last Sold Summary

    • 28% Below List Price
    • $617/SF
    • 28 Days On Market

    Current Estimated Value $1,588,904

    Last Listing Agent Peyton Wallace Studio Realty

    10 Rumpus Ridge Rd, Chilmark, MA 02535
    • /12

      Not Listed For Sale

      99 Cygnet Way, Chilmark, MA 02535

      99 Cygnet Way, Chilmark, MA 02535

      Last Sold Summary

      • 792 Days On Market
      • Last Sold Price $365,000
      • Oct 26, 2015

      Last Listing Agent Russell Maloney Russell Maloney Real Estate

  • /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 $1,369,065 Not Listed For Sale

      31 Cross Rip Ln, Chilmark, MA 02535

      • 1 Bed
      • 1 Bath
      • 512 Sq Ft
      • Built 1999
      31 Cross Rip Ln, Chilmark, MA 02535

      Last Sold Summary

      • 38% Above List Price
      • $1,943/SF
      • 30 Days On Market
      • Last Sold Price $995,000
      • Aug 09, 2023

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /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
    • /31

      Est $3,425,551 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

      • 1% Above List Price
      • $1,478/SF
      • 88 Days On Market
      • Last Sold Price $3,400,000
      • Oct 03, 2022

      Last Listing Agent Peyton Wallace Compass

  • /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
    • /75

      Est $4,001,944 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

      • 3% Above List Price
      • $2,863/SF
      • 49 Days On Market
      • Last Sold Price $3,900,000
      • Nov 28, 2022

      Last Listing Agent Jill Napior Tea Lane Associates

    • /31

      Est $2,228,888 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

      • 19% Above List Price
      • $1,353/SF
      • 11 Days On Market
      • Last Sold Price $1,875,000
      • Mar 01, 2023

      Last Listing Agent Julianna Flanders Flanders Real Estate

    • /17

      Est $2,645,690 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

      • 49% Above List Price
      • $747/SF
      • 4 Days On Market
      • Last Sold Price $1,775,000
      • Sep 15, 2021

      Last Listing Agent Julianna Flanders Flanders Real Estate

    • /2

      Est $5,031,335 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

      Last Sold Summary

      • 1% Below List Price
      • $2,561/SF
      • Last Sold Price $5,000,000

      Last Listing Agent Michelle Kelly Tea Lane Associates

    • /22

      Est $2,571,039 Not Listed For Sale

      1 Smith Ln, Chilmark, MA 02535

      • 4 Beds
      • 4.5 Baths
      • 2,595 Sq Ft
      • Built 1985
      1 Smith Ln, Chilmark, MA 02535

      Last Sold Summary

      • 65% Above List Price
      • $599/SF
      • 62 Days On Market
      • Last Sold Price $1,555,125
      • Aug 15, 2016

      Last Listing Agent Russell Maloney Russell Maloney Real Estate

    • /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

      Last Sold Summary

      • $1,797/SF
      • Last Sold Price $9,025,000

      Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

Showing Results 81 - 120, Page 3 of 18

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