366

Recently Sold Dukes County MA Homes

Section Image
  • /8

    $435,000

    Sold Apr 16, 2026

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539

    • Land
    • 22,651 Sq Ft
    • $836,538 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 131 Days On Market

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

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539
  • /7

    $375,000

    Sold Apr 06, 2026

    99 Cygnet Way Unit 103, Chilmark, MA 02535

    • Land
    • 8,712 Sq Ft
    • $1,875,000 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 120 Days On Market

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    99 Cygnet Way Unit 103, Chilmark, MA 02535
  • /19

    $875,000

    Sold Jul 28, 2026

    15 Second Ave, Oak Bluffs, MA 02557

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $1,683/SF
    • 11 Days On Market

    Current Estimated Value $869,803

    Last Listing Agent Susie Wallo Compass LLC

    15 Second Ave, Oak Bluffs, MA 02557
  • /2

    $15,000,000

    Sold Apr 02, 2026

    38 Cow Bay Rd, Edgartown, MA 02539

    • 6 Beds
    • 8 Baths
    • 5,586 Sq Ft
    • Built 1999

    Last Sold Summary

    • 10% Below List Price
    • $2,685/SF
    • 0 Days On Market

    Last Listing Agent Gerrett Conover Landvest MV

    38 Cow Bay Rd, Edgartown, MA 02539
  • /55

    $2,100,000

    Sold Aug 11, 2026

    25 Pennacook Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 2,516 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $835/SF
    • 45 Days On Market

    Last Listing Agent Nya Clarke Martha's Vineyard Island-Wide Realty

    25 Pennacook Ave, Oak Bluffs, MA 02557
  • /9

    $1,500,000

    Sold Oct 20, 2025

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

    • Land
    • 3.9 Acres
    • $384,615 per Acre

    Last Sold Summary

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

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
  • /29

    $1,075,000

    Sold Feb 26, 2026

    34 Pine Ln, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1984

    Last Sold Summary

    • 14% Below List Price
    • $960/SF
    • 93 Days On Market

    Current Estimated Value $1,233,127

    Last Listing Agent Candy DaRosa Feiner Real Estate

    34 Pine Ln, Vineyard Haven, MA 02568
  • /2

    $3,500,000

    Sold Oct 07, 2025

    339 Lake St, Vineyard Haven, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 2,448 Sq Ft
    • Built 2001

    Last Sold Summary

    • $1,430/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    339 Lake St, Vineyard Haven, MA 02568
  • /22

    $1,575,000

    Sold Nov 24, 2025

    60 Windsor Dr, Edgartown, MA 02539

    • 4 Beds
    • 2 Baths
    • 1,666 Sq Ft
    • Built 1996

    Last Sold Summary

    • 5% Below List Price
    • $945/SF
    • 204 Days On Market

    Current Estimated Value $1,459,173

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

    60 Windsor Dr, Edgartown, MA 02539
  • /42

    $2,448,000

    Sold May 22, 2026

    61 Causeway Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 3,530 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Below List Price
    • $693/SF
    • 51 Days On Market

    Current Estimated Value $2,447,880

    Last Listing Agent Stephanie Roache Donnelly + Co.

    61 Causeway Rd, Vineyard Haven, MA 02568
  • /31

    $7,080,000

    Sold Jul 02, 2026

    54 Fuller St, Edgartown, MA 02539

    • 5 Beds
    • 6.5 Baths
    • 5,454 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $1,298/SF
    • 62 Days On Market

    Current Estimated Value $7,316,115

    Last Listing Agent Gerrett Conover Landvest MV

    54 Fuller St, Edgartown, MA 02539
  • /8

    $1,000,000

    Sold Jan 13, 2026

    48 W Tisbury Rd, Edgartown, MA 02539

    • 3 Beds
    • 3 Baths
    • 1,959 Sq Ft
    • Built 1950

    Last Sold Summary

    • 29% Below List Price
    • $510/SF
    • 86 Days On Market

    Current Estimated Value $1,065,747

    Last Listing Agent Mavis Francis eXp Realty

    48 W Tisbury Rd, Edgartown, MA 02539
  • /35

    $1,000,000

    Sold Jan 21, 2026

    9 Sampson Ave, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 2,046 Sq Ft
    • Built 1985

    Last Sold Summary

    • 20% Below List Price
    • $489/SF
    • 215 Days On Market

    Current Estimated Value $1,081,642

    Last Listing Agent Lynn Buder Sandpiper Realty

    9 Sampson Ave, Edgartown, MA 02539
  • /13

    $2,237,500

    Sold Nov 19, 2025

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

    • 4 Beds
    • 3 Baths
    • 2,299 Sq Ft
    • Built 1974

    Last Sold Summary

    • 16% Below List Price
    • $973/SF
    • 120 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
  • /30

    $968,750

    Sold Jun 05, 2026

    28 Barling Ave, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1981

    Last Sold Summary

    • 8% Below List Price
    • $786/SF
    • 206 Days On Market

    Current Estimated Value $1,016,833

    Last Listing Agent Michael Schweikert Ocean Park Realty Inc

    28 Barling Ave, Vineyard Haven, MA 02568
  • /19

    $1,100,000

    Sold Aug 19, 2026

    34 10th St S, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Built 2006

    Last Sold Summary

    • 8% Below List Price
    • $1,000/SF
    • 58 Days On Market

    Current Estimated Value $1,198,394

    Last Listing Agent Chrissie Teague Insight Realty Group, Inc.

    34 10th St S, Edgartown, MA 02539
  • /34

    $1,675,000

    Sold Dec 08, 2025

    78 Whalers Walk, Edgartown, MA 02539

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft
    • Built 1999

    Last Sold Summary

    • 7% Below List Price
    • $875/SF
    • 88 Days On Market

    Current Estimated Value $1,793,924

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    78 Whalers Walk, Edgartown, MA 02539
  • /2

    $970,000

    Sold Jun 12, 2026

    62 Winter St Unit 2, Edgartown, MA 02539

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft
    • Built 1988

    Last Sold Summary

    • $750/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    62 Winter St Unit 2, Edgartown, MA 02539
  • /14

    $3,867,650

    Sold Nov 21, 2025

    160 Katama Rd, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Below List Price
    • $1,289/SF
    • 101 Days On Market

    Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's

    160 Katama Rd, Edgartown, MA 02539
  • /22

    $1,000,000

    Sold Jun 03, 2026

    31 North Rd, Chilmark, MA 02535

    • 2 Beds
    • 1 Bath
    • 576 Sq Ft
    • Built 1970

    Last Sold Summary

    • 17% Below List Price
    • $1,736/SF
    • 9 Days On Market

    Current Estimated Value $1,019,470

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    31 North Rd, Chilmark, MA 02535
  • /46

    $1,600,000

    Sold Jan 20, 2026

    5 Bayes Hill Cir, Oak Bluffs, MA 02557

    • 4 Beds
    • 2.5 Baths
    • 2,855 Sq Ft
    • Built 1997

    Last Sold Summary

    • 26% Below List Price
    • $560/SF
    • 182 Days On Market

    Last Listing Agent Michele Moore Island Real Estate

    5 Bayes Hill Cir, Oak Bluffs, MA 02557
  • /38

    $3,930,000

    Sold Jun 29, 2026

    71 Stoney Hill Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 5 Baths
    • 5,598 Sq Ft
    • Built 2007

    Last Sold Summary

    • 13% Below List Price
    • $702/SF
    • 372 Days On Market

    Current Estimated Value $3,898,952

    Last Listing Agent Sheila Morse Island Real Estate

    71 Stoney Hill Rd, Vineyard Haven, MA 02568
  • /20

    $1,000,000

    Sold Dec 12, 2025

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 2001

    Last Sold Summary

    • 9% Below List Price
    • $470/SF
    • 13 Days On Market

    Current Estimated Value $1,234,962

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
  • /26

    $1,687,500

    Sold Jul 10, 2026

    103 Meadow View Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 2.5 Baths
    • 2,862 Sq Ft
    • Built 1988

    Last Sold Summary

    • 4% Below List Price
    • $590/SF
    • 31 Days On Market

    Current Estimated Value $1,734,954

    Last Listing Agent Alyson Parker Karen M. Overtoom R.E.

    103 Meadow View Rd, Oak Bluffs, MA 02557
  • /28

    $1,150,000

    Sold May 08, 2026

    18 Windsor Dr, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,294 Sq Ft
    • Built 1981

    Last Sold Summary

    • 15% Above List Price
    • $889/SF
    • 4 Days On Market

    Current Estimated Value $1,145,026

    Last Listing Agent Stephanie Roache Donnelly + Co.

    18 Windsor Dr, Edgartown, MA 02539
  • /35

    $1,817,500

    Sold Feb 27, 2026

    32 Flamingo Dr, Edgartown, MA 02539

    • 5 Beds
    • 3 Baths
    • 2,432 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $747/SF
    • 251 Days On Market

    Current Estimated Value $1,895,735

    Last Listing Agent Skip Dostal Martha's Vineyard R.E.

    32 Flamingo Dr, Edgartown, MA 02539
  • /61

    $1,910,000

    Sold Apr 03, 2026

    28 Pine Tree Ln, Vineyard Haven, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft
    • Built 1974

    Last Sold Summary

    • 15% Below List Price
    • $588/SF
    • 132 Days On Market

    Current Estimated Value $2,094,132

    Last Listing Agent Wendy Harman Compass | Point B

    28 Pine Tree Ln, Vineyard Haven, MA 02568
  • /21

    $895,000

    Sold May 13, 2026

    22 Montgomery Square, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 931 Sq Ft
    • Built 1870

    Last Sold Summary

    • $961/SF
    • 7 Days On Market

    Current Estimated Value $905,359

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    22 Montgomery Square, Oak Bluffs, MA 02557
  • /10

    $4,500,000

    Sold Sep 18, 2026

    7 Marthas Rd, Edgartown, MA 02539

    • 4 Beds
    • 4.5 Baths
    • 3,816 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $1,179/SF
    • 414 Days On Market

    Last Listing Agent Michele Casavant Vineyard Village Realty

    7 Marthas Rd, Edgartown, MA 02539
  • /7

    $600,000

    Sold Nov 04, 2025

    10 Putnam Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • Built 1972

    Last Sold Summary

    • 22% Below List Price
    • $514/SF
    • 39 Days On Market

    Current Estimated Value $704,463

    Last Listing Agent Kathleen Dawson Donnelly + Co.

    10 Putnam Way, Vineyard Haven, MA 02568
  • /20

    $1,225,000

    Sold Mar 16, 2026

    344 Greenwood Ave, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1981

    Last Sold Summary

    • 6% Below List Price
    • $782/SF
    • 75 Days On Market

    Current Estimated Value $1,271,313

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    344 Greenwood Ave, Vineyard Haven, MA 02568
  • /41

    $1,900,000

    Sold May 01, 2026

    36 Smith Hollow Dr, Edgartown, MA 02539

    • 5 Beds
    • 2.5 Baths
    • 2,836 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $670/SF
    • 172 Days On Market

    Current Estimated Value $1,917,498

    Last Listing Agent Katherine Donahue Sandpiper Realty

    36 Smith Hollow Dr, Edgartown, MA 02539
  • /27

    $1,735,000

    Sold Sep 29, 2025

    56 Bridle Path Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 4 Baths
    • 2,526 Sq Ft
    • Built 1996

    Last Sold Summary

    • 13% Below List Price
    • $687/SF
    • 2 Days On Market

    Current Estimated Value $2,166,208

    Last Listing Agent Tina Miller Donnelly + Co.

    56 Bridle Path Rd, Vineyard Haven, MA 02568
  • /15

    $1,000,000

    Sold May 13, 2026

    140 Midland Ave, Tisbury, MA 02568

    • 4 Beds
    • 4 Baths
    • 1,999 Sq Ft
    • Built 1974

    Last Sold Summary

    • 33% Below List Price
    • $500/SF
    • 2 Days On Market

    Last Listing Agent Tina Miller Donnelly + Co

    140 Midland Ave, Tisbury, MA 02568
  • /28

    $1,400,000

    Sold Nov 26, 2025

    5 Scottys Ln, Vineyard Haven, MA 02568

    • 4 Beds
    • 1.5 Baths
    • 1,592 Sq Ft
    • Built 1968

    Last Sold Summary

    • 22% Below List Price
    • $879/SF
    • 126 Days On Market

    Current Estimated Value $1,666,291

    Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    5 Scottys Ln, Vineyard Haven, MA 02568
  • /37

    $2,890,000

    Sold Sep 14, 2026

    10 N Bog Rd, Edgartown, MA 02539

    • 5 Beds
    • 4.5 Baths
    • 3,881 Sq Ft
    • Built 1993

    Last Sold Summary

    • 10% Below List Price
    • $745/SF
    • 40 Days On Market

    Current Estimated Value $2,837,529

    Last Listing Agent Michele Casavant Vineyard Village Realty

    10 N Bog Rd, Edgartown, MA 02539
  • /34

    $3,746,925

    Sold Nov 14, 2025

    39 Sengekontacket Rd, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 2,861 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $1,310/SF
    • 114 Days On Market

    Current Estimated Value $3,668,740

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    39 Sengekontacket Rd, Edgartown, MA 02539
  • /2

    $24,000,000

    Sold Jan 28, 2026

    177 Katama Rd, Edgartown, MA 02539

    • 5 Beds
    • 4 Baths
    • 3,728 Sq Ft
    • Built 1900

    Last Sold Summary

    • $6,438/SF
    • 0 Days On Market

    Current Estimated Value $13,034,517

    Last Listing Agent Thomas Leclair Landvest MV

    177 Katama Rd, Edgartown, MA 02539
  • /37

    $1,705,000

    Sold Mar 24, 2026

    2 Farm Path, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft
    • Built 1992

    Last Sold Summary

    • 15% Below List Price
    • $558/SF
    • 347 Days On Market

    Current Estimated Value $1,733,576

    Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • /23

    $1,500,000

    Sold Sep 25, 2025

    190 Longview Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1995

    Last Sold Summary

    • 15% Below List Price
    • $1,071/SF
    • 43 Days On Market

    Current Estimated Value $1,692,286

    Last Listing Agent Kathleen Kendrick Kendrick Real Estate

    190 Longview Rd, Vineyard Haven, MA 02568

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