1,742

Chilmark Homes

Section Image
    • 4 Bartlett Woods, Chilmark, MA 02535
      4 Bartlett Woods, Chilmark, MA 02535
      4 Bartlett Woods, Chilmark, MA 02535
      /32

      Est $3,056,133 Not Listed For Sale

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

      4 Bartlett Woods, Chilmark, MA 02535

      4 Bartlett Woods, Chilmark, MA 02535
  • 6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    /16

    $3,200,000

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
  • 10 Basin Rd, Chilmark, MA 02535
    10 Basin Rd, Chilmark, MA 02535
    10 Basin 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 $3,133,712

    Last Listing Agent Julianna Flanders Flanders Real Estate

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

      Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 4,967 Sq Ft

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

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535
  • 300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    /40

    $2,995,000

    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and two

    Rebecca V Conroy Conroy & Company R.E., Inc.

    300 North Rd, Chilmark, MA 02535
  • 10 Mollys Way, Chilmark, MA 02535
    10 Mollys Way, Chilmark, MA 02535
    10 Mollys Way, 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 $1,906,624

    Last Listing Agent Peyton Wallace Studio Realty

    10 Mollys Way, Chilmark, MA 02535
    • 34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535
      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535
      34 Ebens Lane & 31 Tower Ln, 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
  • 12 Squibnocket Rd, Chilmark, MA 02535
    12 Squibnocket Rd, 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
    • 70 State Rd, Aquinnah, MA 02535
      70 State Rd, Aquinnah, MA 02535
      70 State Rd, Aquinnah, MA 02535
      /13

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 816 Sq Ft

      70 State Rd, Aquinnah, MA 02535

      70 State Rd, Aquinnah, MA 02535
  • 0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
    /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
    • 0 Beach Lot Quansoo #136, Chilmark, MA 02535
      0 Beach Lot Quansoo #136, Chilmark, MA 02535
      0 Beach Lot Quansoo #136, Chilmark, MA 02535
      /6

      Not Listed For Sale

      0 Beach Lot Quansoo #136, Chilmark, MA 02535

      0 Beach Lot Quansoo #136, Chilmark, MA 02535
  • 9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    /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

    Last Listing Agent Stephanie Roache Donnelly + Co.

    9 Beetlebung Grove Way, Chilmark, MA 02535
    • 0 Gosnold's Way, Chilmark, MA 02535
      0 Gosnold's Way, Chilmark, MA 02535
      0 Gosnold's Way, Chilmark, MA 02535
      /13

      Not Listed For Sale

      0 Gosnold's Way, Chilmark, MA 02535

      0 Gosnold's Way, Chilmark, MA 02535
  • 2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    /52

    $9,525,000 Sold Apr 24, 2025

    2 Squibnocket Rd, Chilmark, MA 02535

    • 6 Beds
    • 5.5 Baths
    • 5,808 Sq Ft
    • Built 2008

    Last Sold Summary

    • 24% Below List Price
    • $1,640/SF
    • 297 Days On Market

    Last Listing Agent Tina Miller Donnelly + Co

    2 Squibnocket Rd, Chilmark, MA 02535
    • 0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
      0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
      0 Beach Lot Quansoo Unit 42634, 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
  • 0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    /2

    $440,000 Sold Sep 22, 2025

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

    • Land
    • 0 Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    • 0 Black Point Road Beach Lot 7, Chilmark, MA 02535
      0 Black Point Road Beach Lot 7, Chilmark, MA 02535
      0 Black Point Road Beach Lot 7, 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
  • 10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    /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 $1,431,567

    Last Listing Agent Peyton Wallace Studio Realty

    10 Rumpus Ridge Rd, Chilmark, MA 02535
    • 5 Oyster Ln, Chilmark, MA 02535
      5 Oyster Ln, Chilmark, MA 02535
      5 Oyster Ln, Chilmark, MA 02535
      /29

      Est $2,105,089 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,108 Sq Ft

      5 Oyster Ln, Chilmark, MA 02535

      5 Oyster Ln, Chilmark, MA 02535
  • 0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    /16

    $475,000 Sold Oct 20, 2025

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

    • Land
    • 0 Acre

    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
    • 15 Marsh Rd, Chilmark, MA 02535
      15 Marsh Rd, Chilmark, MA 02535
      15 Marsh Rd, Chilmark, MA 02535
      /17

      Est $1,984,987 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 800 Sq Ft

      15 Marsh Rd, Chilmark, MA 02535

      15 Marsh Rd, Chilmark, MA 02535
  • 1 Crowberry Ln Unit 19, Chilmark, MA 02535
    1 Crowberry Ln Unit 19, Chilmark, MA 02535
    1 Crowberry Ln Unit 19, Chilmark, MA 02535
    /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
    • 5 Meetinghouse Rd, Chilmark, MA 02535
      5 Meetinghouse Rd, Chilmark, MA 02535
      5 Meetinghouse Rd, Chilmark, MA 02535
      /22

      Est $1,658,925 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,008 Sq Ft

      5 Meetinghouse Rd, Chilmark, MA 02535

      5 Meetinghouse Rd, Chilmark, MA 02535
  • 0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 76 43513, 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
    • 21 Tea Ln, Chilmark, MA 02535
      21 Tea Ln, Chilmark, MA 02535
      21 Tea Ln, Chilmark, MA 02535
      /11

      Est $2,385,541 Not Listed For Sale

      21 Tea Ln, Chilmark, MA 02535

      21 Tea Ln, Chilmark, MA 02535
  • 20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    /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

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

    20 Eliot Ave, Chilmark, MA 02535
    • 31 Tower Ln, Chilmark, MA 02535
      31 Tower Ln, Chilmark, MA 02535
      31 Tower Ln, Chilmark, MA 02535
      /6

      Est $2,556,000 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 1,135 Sq Ft

      31 Tower Ln, Chilmark, MA 02535

      31 Tower Ln, Chilmark, MA 02535
    • 99 Cygnet Way, Chilmark, MA 02535
      99 Cygnet Way, Chilmark, MA 02535
      99 Cygnet Way, Chilmark, MA 02535
      /8

      Not Listed For Sale

      99 Cygnet Way, Chilmark, MA 02535

      99 Cygnet Way, Chilmark, MA 02535
    • 1 Old Rd N, Chilmark, MA 02535
      1 Old Rd N, Chilmark, MA 02535
      1 Old Rd N, Chilmark, MA 02535
      /35

      Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 516 Sq Ft

      1 Old Rd N, Chilmark, MA 02535

      1 Old Rd N, Chilmark, MA 02535
    • 31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      /20

      Est $1,298,650 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 512 Sq Ft

      31 Cross Rip Ln, Chilmark, MA 02535

      31 Cross Rip Ln, Chilmark, MA 02535
    • 68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      /31

      Est $3,476,762 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,300 Sq Ft

      68 Meeting House Rd, Chilmark, MA 02535

      68 Meeting House Rd, Chilmark, MA 02535
    • 4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      /75

      Est $4,040,356 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,362 Sq Ft

      4 Tilton Rd, Chilmark, MA 02535

      4 Tilton Rd, Chilmark, MA 02535
    • 22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      /17

      Est $2,712,565 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,375 Sq Ft

      22 Tabor Hills, Chilmark, MA 02535

      22 Tabor Hills, Chilmark, MA 02535
    • 24 Blacksmith Valley Rd, Chilmark, MA 02535
      24 Blacksmith Valley Rd, Chilmark, MA 02535
      /2

      Est $5,021,230 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,952 Sq Ft

      24 Blacksmith Valley Rd, Chilmark, MA 02535

      24 Blacksmith Valley Rd, Chilmark, MA 02535
    • 15 Lake Rd, Chilmark, MA 02535
      15 Lake Rd, Chilmark, MA 02535
      15 Lake Rd, Chilmark, MA 02535
      /21

      Est $3,806,284 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 1,980 Sq Ft

      15 Lake Rd, Chilmark, MA 02535

      15 Lake Rd, Chilmark, MA 02535
    • 5 Guerin Ln, Chilmark, MA 02535
      5 Guerin Ln, Chilmark, MA 02535
      5 Guerin Ln, Chilmark, MA 02535
      /25

      Est $3,392,174 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,929 Sq Ft

      5 Guerin Ln, Chilmark, MA 02535

      5 Guerin Ln, Chilmark, MA 02535
    • 1 Smith Ln, Chilmark, MA 02535
      1 Smith Ln, Chilmark, MA 02535
      /2

      Est $2,530,226 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,000 Sq Ft

      1 Smith Ln, Chilmark, MA 02535

      1 Smith Ln, Chilmark, MA 02535
    • 18 Austin Pasture, Chilmark, MA 02535
      18 Austin Pasture, Chilmark, MA 02535
      18 Austin Pasture, Chilmark, MA 02535
      /39

      Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 4,000 Sq Ft

      18 Austin Pasture, Chilmark, MA 02535

      18 Austin Pasture, Chilmark, MA 02535
    • 26 Pinkletink Rd, Chilmark, MA 02535
      26 Pinkletink Rd, Chilmark, MA 02535
      26 Pinkletink Rd, Chilmark, MA 02535
      /30

      Est $3,737,700 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,748 Sq Ft

      26 Pinkletink Rd, Chilmark, MA 02535

      26 Pinkletink Rd, Chilmark, MA 02535
    • 5 N Slope Ln, Chilmark, MA 02535
      5 N Slope Ln, Chilmark, MA 02535
      5 N Slope Ln, Chilmark, MA 02535
      /33

      Est $3,348,012 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,853 Sq Ft

      5 N Slope Ln, Chilmark, MA 02535

      5 N Slope Ln, Chilmark, MA 02535

Showing Results 81 - 120, Page 3 of 18

Massachusetts Dukes County Marthas Vineyard Chilmark

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group