4,276

Oak Bluffs, MA Homes

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  • 168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
    168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
    168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
    /20

    $821,000 Sold Jun 17, 2025

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

    • Land
    • 1.4 Acres
    • $586,429 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 0 Days On Market

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
    • 35 Skiffs Ln, Vineyard Haven, MA 02568
      35 Skiffs Ln, Vineyard Haven, MA 02568
      35 Skiffs Ln, Vineyard Haven, MA 02568
      /16

      Est $1,286,168 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,408 Sq Ft

      35 Skiffs Ln, Vineyard Haven, MA 02568

      35 Skiffs Ln, Vineyard Haven, MA 02568
  • 157 Ben Chase Rd, West Tisbury, MA 02575
    157 Ben Chase Rd, West Tisbury, MA 02575
    157 Ben Chase Rd, West Tisbury, MA 02575
    /59

    $2,250,000

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

    157 Ben Chase Rd, West Tisbury, MA 02575

    You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

    Madelyn Silvia Wallace & Co. Sotheby's

    157 Ben Chase Rd, West Tisbury, MA 02575
  • 3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    /48

    $1,775,000 Sold Nov 07, 2025

    3 Fulling Mill Rd, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $1,027/SF
    • 170 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
    • 43 Skiffs Ln, Vineyard Haven, MA 02568
      43 Skiffs Ln, Vineyard Haven, MA 02568
      43 Skiffs Ln, Vineyard Haven, MA 02568
      /37

      Est $1,213,363 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft

      43 Skiffs Ln, Vineyard Haven, MA 02568

      43 Skiffs Ln, Vineyard Haven, MA 02568
  • 51 Black Brook Crossing Rd, West Tisbury, MA 02568
    51 Black Brook Crossing Rd, West Tisbury, MA 02568
    51 Black Brook Crossing Rd, West Tisbury, MA 02568
    /36

    $1,950,000 Sold Jul 02, 2025

    51 Black Brook Crossing Rd, West Tisbury, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 2,691 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $725/SF
    • 30 Days On Market

    Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

    51 Black Brook Crossing Rd, West Tisbury, MA 02568
    • 48 Forest Rd, Vineyard Haven, MA 02568
      48 Forest Rd, Vineyard Haven, MA 02568
      48 Forest Rd, Vineyard Haven, MA 02568
      /26

      Est $4,779,032 Not Listed For Sale

      • 8 Beds
      • 4 Baths
      • 4,800 Sq Ft

      48 Forest Rd, Vineyard Haven, MA 02568

      48 Forest Rd, Vineyard Haven, MA 02568
  • 18 Homeward Way, Chilmark, MA 02535
    18 Homeward Way, Chilmark, MA 02535
    18 Homeward Way, 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

    Last Listing Agent Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
    • 33 Hidden Village Rd, Vineyard Haven, MA 02568
      33 Hidden Village Rd, Vineyard Haven, MA 02568
      33 Hidden Village Rd, Vineyard Haven, MA 02568
      /26

      Est $1,605,380 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 1,968 Sq Ft

      33 Hidden Village Rd, Vineyard Haven, MA 02568

      33 Hidden Village Rd, Vineyard Haven, MA 02568
  • 55 Charles Neck Way, Vineyard Haven, MA 02568
    55 Charles Neck Way, Vineyard Haven, MA 02568
    55 Charles Neck Way, Vineyard Haven, MA 02568
    /35

    $1,837,500 Sold Apr 18, 2025

    55 Charles Neck Way, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 1,654 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $1,111/SF
    • 182 Days On Market

    Current Estimated Value $1,819,445

    Last Listing Agent Wendy Harman Compass | Point B

    55 Charles Neck Way, Vineyard Haven, MA 02568
    • 41 Hidden Village Rd, Vineyard Haven, MA 02568
      41 Hidden Village Rd, Vineyard Haven, MA 02568
      41 Hidden Village Rd, Vineyard Haven, MA 02568
      /30

      Est $2,498,674 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,540 Sq Ft

      41 Hidden Village Rd, Vineyard Haven, MA 02568

      41 Hidden Village Rd, Vineyard Haven, MA 02568
  • 14 Galway Rd, Vineyard Haven, MA 02568
    14 Galway Rd, Vineyard Haven, MA 02568
    14 Galway Rd, Vineyard Haven, MA 02568
    /15

    $1,150,000 Sold May 30, 2025

    14 Galway Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 1.5 Baths
    • 1,338 Sq Ft
    • Built 1966

    Last Sold Summary

    • 8% Below List Price
    • $859/SF
    • 48 Days On Market

    Current Estimated Value $1,165,505

    Last Listing Agent Michele Casavant Vineyard Village Realty

    14 Galway Rd, Vineyard Haven, MA 02568
    • 12 Lily Farm Rd, Vineyard Haven, MA 02568
      12 Lily Farm Rd, Vineyard Haven, MA 02568
      12 Lily Farm Rd, Vineyard Haven, MA 02568
      /30

      Est $1,523,464 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,560 Sq Ft

      12 Lily Farm Rd, Vineyard Haven, MA 02568

      12 Lily Farm Rd, Vineyard Haven, MA 02568
  • 146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo 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

    Last Listing Agent Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
    • 1 Carroll Ln, Chilmark, MA 02535
      1 Carroll Ln, Chilmark, MA 02535
      1 Carroll Ln, Chilmark, MA 02535
      /5

      Est $558,353 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 708 Sq Ft

      1 Carroll Ln, Chilmark, MA 02535

      1 Carroll Ln, Chilmark, MA 02535
  • 32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, 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
    • 7 Flanders Ln, Chilmark, MA 02535
      7 Flanders Ln, Chilmark, MA 02535
      7 Flanders Ln, Chilmark, MA 02535
      /29

      Est $1,732,574 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      7 Flanders Ln, Chilmark, MA 02535

      7 Flanders Ln, Chilmark, MA 02535
  • 23 Oak Ln, Vineyard Haven, MA 02568
    23 Oak Ln, Vineyard Haven, MA 02568
    /2

    $2,400,000 Sold Feb 04, 2025

    23 Oak Ln, Vineyard Haven, MA 02568

    • 6 Beds
    • 4.5 Baths
    • 3,035 Sq Ft
    • Built 2007

    Last Sold Summary

    • 20% Below List Price
    • $791/SF
    • 213 Days On Market

    Current Estimated Value $2,488,468

    Last Listing Agent Lynn Buder Sandpiper Realty Inc

    23 Oak Ln, Vineyard Haven, MA 02568
    • 12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      /13

      Est $1,535,733 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 640 Sq Ft

      12 Harbor Hill Rd, Chilmark, MA 02535

      12 Harbor Hill Rd, 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
    • 1 Pond Mark, Chilmark, MA 02535
      1 Pond Mark, Chilmark, MA 02535
      1 Pond Mark, Chilmark, MA 02535
      /18

      Est $4,086,623 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft

      1 Pond Mark, Chilmark, MA 02535

      1 Pond Mark, Chilmark, MA 02535
  • 35 Woody Bottom Rd, West Tisbury, MA 02575
    35 Woody Bottom Rd, West Tisbury, MA 02575
    35 Woody Bottom Rd, West Tisbury, MA 02575
    /32

    $2,278,000 Sold Aug 01, 2025

    35 Woody Bottom Rd, West Tisbury, MA 02575

    • 5 Beds
    • 3.5 Baths
    • 2,685 Sq Ft
    • Built 1998

    Last Sold Summary

    • 9% Below List Price
    • $848/SF
    • 139 Days On Market

    Current Estimated Value $2,286,209

    Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

    35 Woody Bottom Rd, West Tisbury, MA 02575
    • 5 Ocean View Farm Rd, Chilmark, MA 02535
      5 Ocean View Farm Rd, Chilmark, MA 02535
      5 Ocean View Farm Rd, Chilmark, MA 02535
      /12

      Est $2,449,380 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,342 Sq Ft

      5 Ocean View Farm Rd, Chilmark, MA 02535

      5 Ocean View Farm Rd, Chilmark, MA 02535
  • 34 S Pond Rd, Vineyard Haven, MA 02568
    34 S Pond Rd, Vineyard Haven, MA 02568
    34 S Pond Rd, Vineyard Haven, MA 02568
    /50

    $3,000,000 Sold Apr 29, 2025

    34 S Pond Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 3,311 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Above List Price
    • $906/SF

    Current Estimated Value $2,924,754

    Last Listing Agent Stephanie Roache Donnelly + Co

    34 S Pond Rd, Vineyard Haven, MA 02568
    • 27 Ocean View Farm Rd, Chilmark, MA 02535
      27 Ocean View Farm Rd, Chilmark, MA 02535
      27 Ocean View Farm Rd, Chilmark, MA 02535
      /19

      Est $2,754,266 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,450 Sq Ft

      27 Ocean View Farm Rd, Chilmark, MA 02535

      27 Ocean View Farm Rd, Chilmark, MA 02535
  • 140 Merry Farm Rd, Vineyard Haven, MA 02568
    140 Merry Farm Rd, Vineyard Haven, MA 02568
    140 Merry Farm Rd, Vineyard Haven, MA 02568
    /32

    $3,925,000 Sold Jul 01, 2025

    140 Merry Farm Rd, Vineyard Haven, MA 02568

    • 6 Beds
    • 7 Baths
    • 5,603 Sq Ft
    • Built 1995

    Last Sold Summary

    • 8% Below List Price
    • $701/SF
    • 238 Days On Market

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

    140 Merry Farm Rd, Vineyard Haven, MA 02568
    • 276 South Rd, Chilmark, MA 02535
      276 South Rd, Chilmark, MA 02535
      276 South Rd, Chilmark, MA 02535
      /69

      Est $2,406,935 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,034 Sq Ft

      276 South Rd, Chilmark, MA 02535

      276 South 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
    • 2 Rockrose Path, Chilmark, MA 02535
      2 Rockrose Path, Chilmark, MA 02535
      2 Rockrose Path, Chilmark, MA 02535
      /37

      Est $2,068,421 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,900 Sq Ft

      2 Rockrose Path, Chilmark, MA 02535

      2 Rockrose Path, Chilmark, MA 02535
  • 21 Coffins Field Rd, Edgartown, MA 02539
    21 Coffins Field Rd, Edgartown, MA 02539
    21 Coffins Field Rd, Edgartown, MA 02539
    /47

    $1,595,500 Sold Jun 23, 2025

    21 Coffins Field Rd, Edgartown, MA 02539

    • 5 Beds
    • 3 Baths
    • 1,822 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $876/SF
    • 73 Days On Market

    Current Estimated Value $1,700,273

    Last Listing Agent Helena Kirschenbaum Studio Realty

    21 Coffins Field Rd, Edgartown, MA 02539
    • 23 Black Point Rd, Chilmark, MA 02535
      23 Black Point Rd, Chilmark, MA 02535
      23 Black Point Rd, Chilmark, MA 02535
      /20

      Est $2,780,935 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft

      23 Black Point Rd, Chilmark, MA 02535

      23 Black Point Rd, Chilmark, MA 02535
  • 50 Bradley Martin Rd, Vineyard Haven, MA 02568
    50 Bradley Martin Rd, Vineyard Haven, MA 02568
    50 Bradley Martin Rd, Vineyard Haven, MA 02568
    /37

    $1,925,000 Sold Aug 28, 2025

    50 Bradley Martin Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $1,109/SF
    • 0 Days On Market

    Current Estimated Value $1,650,646

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

    50 Bradley Martin Rd, Vineyard Haven, MA 02568
    • 3 Pepperbush Ln, Chilmark, MA 02535
      3 Pepperbush Ln, Chilmark, MA 02535
      3 Pepperbush Ln, Chilmark, MA 02535
      /21

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,686 Sq Ft

      3 Pepperbush Ln, Chilmark, MA 02535

      3 Pepperbush Ln, Chilmark, MA 02535
  • 14 Rebekahs Way, Vineyard Haven, MA 02568
    14 Rebekahs Way, Vineyard Haven, MA 02568
    14 Rebekahs Way, Vineyard Haven, MA 02568
    /24

    $1,875,000 Sold Dec 08, 2025

    14 Rebekahs Way, Vineyard Haven, MA 02568

    • 5 Beds
    • 3 Baths
    • 1,916 Sq Ft
    • Built 1998

    Last Sold Summary

    • 4% Below List Price
    • $979/SF
    • 22 Days On Market

    Last Listing Agent Sheila Morse Island Real Estate

    14 Rebekahs Way, Vineyard Haven, MA 02568
    • 50 South Rd, Chilmark, MA 02535
      50 South Rd, Chilmark, MA 02535
      50 South Rd, Chilmark, MA 02535
      /29

      Est $2,389,190 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,427 Sq Ft

      50 South Rd, Chilmark, MA 02535

      50 South Rd, Chilmark, MA 02535
  • 496 Lamberts Cove Rd, Vineyard Haven, MA 02568
    496 Lamberts Cove Rd, Vineyard Haven, MA 02568
    496 Lamberts Cove Rd, Vineyard Haven, MA 02568
    /22

    $1,115,000 Sold Mar 14, 2025

    496 Lamberts Cove Rd, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 1,286 Sq Ft
    • Built 1955

    Last Sold Summary

    • 9% Below List Price
    • $867/SF
    • 212 Days On Market

    Current Estimated Value $1,150,898

    Last Listing Agent Stephanie Roache Donnelly + Co

    496 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • 16 South Rd, Chilmark, MA 02535
      16 South Rd, Chilmark, MA 02535
      16 South Rd, Chilmark, MA 02535
      /50

      Est $2,307,508 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,350 Sq Ft

      16 South Rd, Chilmark, MA 02535

      16 South Rd, Chilmark, 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
    • 99 Hammett Rd, Chilmark, MA 02535
      99 Hammett Rd, Chilmark, MA 02535
      99 Hammett Rd, Chilmark, MA 02535
      /24

      Est $2,420,206 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 2,405 Sq Ft

      99 Hammett Rd, Chilmark, MA 02535

      99 Hammett Rd, Chilmark, MA 02535
  • 137 Charles Neck Way, Vineyard Haven, MA 02568
    137 Charles Neck Way, Vineyard Haven, MA 02568
    137 Charles Neck Way, Vineyard Haven, MA 02568
    /26

    $1,850,000 Sold May 14, 2025

    137 Charles Neck Way, Vineyard Haven, MA 02568

    • 5 Beds
    • 4 Baths
    • 2,610 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $709/SF
    • 8 Days On Market

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

    137 Charles Neck Way, Vineyard Haven, MA 02568

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Massachusetts Dukes County Oak Bluffs

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