20,060

Dukes County, MA Homes

Section Image
  • /29

    $1,150,000 Sold Dec 16, 2025

    52 Old Coach Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $887/SF
    • 18 Days On Market

    Current Estimated Value $1,177,077

    Last Listing Agent Kathleen Kendrick Kathleen Kendrick

    52 Old Coach Rd, Vineyard Haven, MA 02568
    • /20

      Est $1,001,731 Not Listed For Sale

      33 Renear St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1950
      33 Renear St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 4% Above List Price
      • $803/SF
      • 7 Days On Market

      Last Sold Price $964,000

      Last Listing Agent Tina Miller Donnelly + Co.

  • /21

    $1,775,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft

    90 Schoolhouse Rd, Edgartown, MA 02539

    Just a few blocks to historic Edgartown Village from this updated beach house in desirable Edgartown Estates. The open living area features decorative wood beams, a wood stove, designer tile flooring, and sliding doors to an expansive wraparound Trex deck (2018), creating seamless indoor-outdoor living. The expanded kitchen (2018) includes granite countertops, stainless steel appliances, ample

    Dawn Bellante-Holand Sandpiper Realty

    90 Schoolhouse Rd, Edgartown, MA 02539
  • /38

    $1,875,000 Sold Apr 01, 2025

    83 Dolan Ave, Vineyard Haven, MA 02568

    • 5 Beds
    • 4.5 Baths
    • 3,841 Sq Ft
    • Built 1994

    Last Sold Summary

    • 1% Below List Price
    • $488/SF
    • 24 Days On Market

    Current Estimated Value $1,838,313

    Last Listing Agent Courtney Marek Sandpiper Realty

    83 Dolan Ave, Vineyard Haven, MA 02568
    • /17

      Est $988,595 Not Listed For Sale

      146 Edgartown Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,214 Sq Ft
      • Built 1958
      146 Edgartown Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7% Below List Price
      • $873/SF
      • 163 Days On Market

      Last Sold Price $1,060,000

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

  • /8

    $925,000

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    260 The Blvd, Edgartown, MA 02539

    Two-bedroom, one bath, renovated cottage in Ocean Heights, Edgartown, offering a classic island “camp” charm with a thoroughly modern interior. Over three phases of work (2001, 2021, 2025), the owners have rebuilt key exterior elements, upgraded major systems, and fully refreshed the living space to create a cozy move-in-ready home. The central living area features a cathedral ceiling and large

    Sean Federowicz Landmarks at TODAY Real Estate

    260 The Blvd, Edgartown, MA 02539
  • /21

    $435,000 Sold Aug 26, 2025

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 20 Days On Market

    Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    • /2

      Est $3,622,501 Not Listed For Sale

      36 Burts Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 7 Baths
      • 4,342 Sq Ft
      • Built 2004
      36 Burts Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 23% Above List Price
      • $679/SF
      • 116 Days On Market

      Last Sold Price $2,950,000

      Last Listing Agent Lynn Buder Sandpiper Realty Inc

  • /2

    $674,000

    • Land
    • 0.49 Acre
    • $1,375,510 per Acre

    56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568

    Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either

    Marilyn Moses Ocean Park Realty Inc

    56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568
  • /34

    $2,001,001 Sold Sep 19, 2025

    17 Sutton's Way, Edgartown, MA 02539

    • 2 Beds
    • 1.5 Baths
    • 1,746 Sq Ft
    • Built 1985

    Last Sold Summary

    • 9% Below List Price
    • $1,146/SF
    • 116 Days On Market

    Last Listing Agent Carson Crissman Compass | Point B

    17 Sutton's Way, Edgartown, MA 02539
    • /16

      Est $1,786,011 Not Listed For Sale

      39 Burts Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 2,068 Sq Ft
      • Built 1965
      39 Burts Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 1% Above List Price
      • $858/SF
      • 141 Days On Market

      Last Sold Price $1,775,000

      Last Listing Agent Lynn Buder Sandpiper Realty Inc

  • /6

    $1,595,000

    • Land
    • 3.2 Acres
    • $498,438 per Acre

    9 Beach Pebble Rd, Vineyard Haven, MA 02568

    Vacant land in West Tisbury's Makonikey Community with access to the beautiful Lower Makonikey Association beach. This rare offering spans over 3 acres, with a 1.4-acre area providing the ideal location for a substantial residence in keeping with the distinguished homes that define this exclusive neighborhood. This property presents a unique opportunity to create an exceptional island retreat.

    Cassie Bradley Wallace & Co. Sotheby's International Realty

    9 Beach Pebble Rd, Vineyard Haven, MA 02568
  • /42

    $3,710,000 Sold Mar 12, 2026

    15 Old Farm Rd, Chilmark, MA 02535

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft
    • Built 2002

    Last Sold Summary

    • 13% Below List Price
    • $1,170/SF
    • 136 Days On Market

    Current Estimated Value $3,965,571

    Last Listing Agent Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
    • /42

      Est $1,837,650 Not Listed For Sale

      201 Lagoon Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,677 Sq Ft
      • Built 1870
      201 Lagoon Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 5% Above List Price
      • $1,047/SF
      • 209 Days On Market

      Last Sold Price $1,755,000

      Last Listing Agent Janna O'Loughlin Portfolio Properties

  • /2

    $625,000 Under Contract

    • Land
    • 0.28 Acre
    • $2,269,426 per Acre

    77 Sixth St N Unit 160, Edgartown, MA 02539

    *All information should be confirmed with the town boards. From BOH - Lot can support a 2 bedroom system with a standard Title 5 or 3 bedrooms with an enhanced system.From Water Department - Town water runs down Sixth Street N. Buyer will need to hook up from the road.From Building/Zoning Department - Lot can support a house and an ADU, by right, with proper permitting.From Wastewater

    Sheila Morse Island Real Estate

    77 Sixth St N Unit 160, Edgartown, MA 02539
  • /13

    $1,195,000 Sold May 22, 2025

    34 10th St S, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,110 Sq Ft
    • Built 2006

    Last Sold Summary

    • $1,077/SF
    • 8 Days On Market

    Current Estimated Value $1,148,647

    Last Listing Agent Rose Ryley Sandpiper Realty Inc

    34 10th St S, Edgartown, MA 02539
    • /25

      Est $1,143,537 Not Listed For Sale

      160 Causeway Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 1948
      160 Causeway Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 13% Above List Price
      • $570/SF
      • 115 Days On Market

      Last Sold Price $1,012,500

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

  • /29

    $2,500,000

    • 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
  • /2

    $1,775,000 Sold Mar 02, 2026

    14 Chapman Ave, Oak Bluffs, MA 02557

    • 5 Beds
    • 2 Baths
    • 1,469 Sq Ft
    • Built 1890

    Last Sold Summary

    • $1,208/SF
    • 0 Days On Market

    Current Estimated Value $1,611,258

    Last Listing Agent LINK Email Cache LINK

    14 Chapman Ave, Oak Bluffs, MA 02557
    • /25

      Est $900,231 Not Listed For Sale

      21 Walker Way, Vineyard Haven, MA 02568

      • 1 Bed
      • 1 Bath
      • 1,244 Sq Ft
      • Built 1940
      21 Walker Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24% Above List Price
      • $583/SF
      • 236 Days On Market

      Last Sold Price $725,000

      Last Listing Agent David Holmberg HomeSmart Heritage Realty

  • /2

    $899,000 Pending

    • Land
    • 4.2 Acres
    • $214,048 per Acre

    5A2.12 State Rd, Tisbury, MA 02568

    This is a beautiful 3.5 acre piece of land! Stunning and Peaceful!

    Fred Mascolo Jane Brown Assoc.

    5A2.12 State Rd, Tisbury, MA 02568
  • /16

    $800,000 Sold Sep 04, 2025

    21 Norris Ave, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 1,086 Sq Ft
    • Built 1948

    Last Sold Summary

    • $737/SF
    • 16 Days On Market

    Current Estimated Value $821,049

    Last Listing Agent Rene Ben David Ocean Park Realty Inc

    21 Norris Ave, Vineyard Haven, MA 02568
    • /6

      Est $582,203 Not Listed For Sale

      92 Rogers Farm Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • Built 1900
      92 Rogers Farm Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 13% Above List Price
      • $254/SF
      • 40 Days On Market

      Last Sold Price $515,000

      Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  • /4

    $474,000

    • Land
    • 0.55 Acre
    • $861,818 per Acre

    11 Boylston Dr, Edgartown, MA 02539

    A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island's top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    11 Boylston Dr, Edgartown, MA 02539
  • /31

    $941,000 Sold Oct 03, 2025

    4 Quail Run Unit 7, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • $711/SF
    • 52 Days On Market

    Current Estimated Value $934,865

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    4 Quail Run Unit 7, Oak Bluffs, MA 02557
    • /19

      Est $975,065 Not Listed For Sale

      238 State Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,184 Sq Ft
      • Built 1920
      238 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 5% Above List Price
      • $781/SF
      • 83 Days On Market

      Last Sold Price $925,000

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /2

    $10,850,000

    • 7 Beds
    • 8 Baths
    • 12,051 Sq Ft

    14 Trapps Pond Rd, Edgartown, MA 02539

    Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. Thisis one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in aVineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from theoversized

    Gerret Conover LandVest MV

    14 Trapps Pond Rd, Edgartown, MA 02539
  • /9

    $900,000 Sold Oct 10, 2025

    25 N Vine Ln Unit 70.3, West Tisbury, MA 02568

    • Land
    • 3.73 Acres
    • $241,287 per Acre

    Last Sold Summary

    • 33% Below List Price
    • 462 Days On Market

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
    • /25

      Est $1,189,267 Not Listed For Sale

      112 Spring St, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,171 Sq Ft
      • Built 1929
      112 Spring St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 8% Above List Price
      • $939/SF
      • 41 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Stephanie Burke Portfolio Properties

  • /19

    $1,195,000

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

    3 Kims Way, Oak Bluffs, MA 02557

    Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    3 Kims Way, Oak Bluffs, MA 02557
  • /26

    $782,000 Sold Mar 06, 2026

    24 School St, Oak Bluffs, MA 02557

    • 2 Beds
    • 1 Bath
    • 861 Sq Ft
    • Built 1925

    Last Sold Summary

    • 11% Below List Price
    • $908/SF
    • 86 Days On Market

    Current Estimated Value $881,297

    Last Listing Agent Stephanie Roache Donnelly + Co.

    24 School St, Oak Bluffs, MA 02557
    • /23

      Est $1,181,812 Not Listed For Sale

      180 Main St Unit 30, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1860
      180 Main St Unit 30, Vineyard Haven, MA 02568

      Last Sold Summary

      • 1% Above List Price
      • $904/SF
      • 96 Days On Market

      Last Sold Price $1,175,000

      Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

  • /32

    $3,895,000 Pending

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

    44 Plantingfield Way, Edgartown, MA 02539

    Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round property offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. The property is currently configured as a three-bedroom, 1-1/2 bathroom main house with a 1BR/1BA accessory apartment over a one-car, detached garage on a

    David Dickinson Compass

    44 Plantingfield Way, Edgartown, MA 02539
  • /42

    $1,250,000 Sold Sep 25, 2025

    58 Weaver Ct, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,210 Sq Ft
    • Built 1969

    Last Sold Summary

    • 22% Below List Price
    • $566/SF
    • 137 Days On Market

    Current Estimated Value $1,381,360

    Last Listing Agent Skip Dostal, Jr Martha's Vineyard Real Estate

    58 Weaver Ct, Vineyard Haven, MA 02568
    • /24

      Est $1,736,658 Not Listed For Sale

      70 Tashmoo Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 3,298 Sq Ft
      • Built 1920
      70 Tashmoo Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16% Above List Price
      • $455/SF
      • 88 Days On Market

      Last Sold Price $1,500,000

      Last Listing Agent Tina Miller Donnelly + Co.

  • /24

    $1,999,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Blending 1920s charm with modern luxury, this beautifully renovated home is tucked into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • /7

    $2,083,500 Sold Dec 19, 2025

    209 Chappaquiddick Rd, Edgartown, MA 02539

    • 5 Beds
    • 3 Baths
    • 3,475 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Below List Price
    • $600/SF

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

    209 Chappaquiddick Rd, Edgartown, MA 02539
    • /19

      Est $1,216,589 Not Listed For Sale

      26 Daggett Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,372 Sq Ft
      • Built 1904
      26 Daggett Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 1% Below List Price
      • $898/SF
      • 181 Days On Market

      Last Sold Price $1,232,500

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

  • /2

    $1,250,000

    • 1 Bed
    • 1 Bath
    • 855 Sq Ft

    0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

    Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

    Peyton Wallace Studio Realty

    0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
  • /32

    $941,000 Sold Oct 03, 2025

    4 Quail Run Rd, Oak Bluffs, MA 02568

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • $711/SF
    • 64 Days On Market

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    4 Quail Run Rd, Oak Bluffs, MA 02568

Showing Results 601 - 640, Page 16 of 18

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