19,346

Dukes County, MA Homes

Section Image
  • /65

    $2,275,000

    Sold May 14, 2026

    69 Whalers Walk, Edgartown, MA 02539

    • 4 Beds
    • 2.5 Baths
    • 2,760 Sq Ft
    • Built 1997

    Last Sold Summary

    • 5% Below List Price
    • $824/SF
    • 46 Days On Market

    Current Estimated Value $2,256,035

    Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

    69 Whalers Walk, Edgartown, MA 02539
    • /44

      Est $7,292,979

      Not Listed For Sale

      1115 Main St, Vineyard Haven, MA 02568

      • 11 Beds
      • 10 Baths
      • 7,026 Sq Ft
      • Built 1893
      1115 Main St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 280 Days On Market

      Last Listing Agent Gerrett Conover Landvest MV

  • /26

    $3,850,000

    Open Sun 1PM - 3PM
    • Land
    • 1.14 Acres
    • $3,377,193 per Acre

    10 Pease Point Rd Unit 57, Edgartown, MA 02539

    PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned at the end of a private drive, on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Possibility of a fourth-bedroom with proper

    Emma Bryant Studio Realty

    10 Pease Point Rd Unit 57, Edgartown, MA 02539
  • /37

    $2,495,000

    Sold Nov 20, 2025

    16 Mockingbird Dr, Edgartown, MA 02539

    • 4 Beds
    • 6 Baths
    • 2,694 Sq Ft
    • Built 2016

    Last Sold Summary

    • 6% Below List Price
    • $926/SF
    • 146 Days On Market

    Current Estimated Value $2,635,198

    Last Listing Agent Emma Kennedy Sandpiper Realty

    16 Mockingbird Dr, Edgartown, MA 02539
    • /47

      Est $2,400,668

      Not Listed For Sale

      42 Hagerty Dr, Vineyard Haven, MA 02568

      • 4 Beds
      • 4.5 Baths
      • 2,569 Sq Ft
      • Built 1970
      42 Hagerty Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Bobbi Reed Viewpoints

  • /26

    $1,850,000

    • 4 Beds
    • 2 Baths
    • 1,833 Sq Ft

    22 Old Harbor Ln, Oak Bluffs, MA 02557

    Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

    Lisa Stewart Sandpiper Realty, Inc.

    22 Old Harbor Ln, Oak Bluffs, MA 02557
  • /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 $1,853,266

    Last Listing Agent LINK Email Cache LINK

    14 Chapman Ave, Oak Bluffs, MA 02557
    • /16

      Est $1,363,746

      Not Listed For Sale

      222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

      • 2 Beds
      • 3 Baths
      • 1,750 Sq Ft
      • Built 1988
      222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /4

    $1,800,000

    • Land
    • 1.1 Acres
    • $1,635,026 per Acre

    0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568

    This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and heavily wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful

    Gerrett Conover Landvest MV

    0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568
  • /35

    $2,210,000

    Sold Jul 23, 2026

    17 Oakdale Dr, Edgartown, MA 02539

    • 3 Beds
    • 3 Baths
    • 2,126 Sq Ft
    • Built 1955

    Last Sold Summary

    • 3% Above List Price
    • $1,040/SF
    • 0 Days On Market

    Current Estimated Value $2,207,428

    Last Listing Agent Wendy Harman Compass

    17 Oakdale Dr, Edgartown, MA 02539
    • /28

      Est $1,277,864

      Not Listed For Sale

      208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1988
      208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Perry Patterson MV Luxury Homes

  • /70

    $5,295,000

    $200K PRICE DROP
    • 3 Beds
    • 7 Baths
    • 3,608 Sq Ft

    385 Barnes Rd, Vineyard Haven, MA 02568

    SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and

    Stephanie Roache Donnelly + Co

    385 Barnes Rd, Vineyard Haven, MA 02568
  • /27

    $2,600,000

    Sold Jun 26, 2026

    2 Cosmos Way, Edgartown, MA 02539

    • 4 Beds
    • 2.5 Baths
    • 2,428 Sq Ft
    • Built 1993

    Last Sold Summary

    • 7% Below List Price
    • $1,071/SF
    • 19 Days On Market

    Current Estimated Value $2,773,968

    Last Listing Agent Jennifer O'hanlon Compass

    2 Cosmos Way, Edgartown, MA 02539
    • /86

      Est $1,638,930

      Not Listed For Sale

      176 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

      • 3 Beds
      • 3.5 Baths
      • 2,455 Sq Ft
      • Built 1988
      176 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

      Last Sold Summary

      • 187 Days On Market

      Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

  • /14

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

    Peyton Wallace Studio Realty

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
  • /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 $841,205

    Last Listing Agent Rene Ben David Ocean Park Realty Inc

    21 Norris Ave, Vineyard Haven, MA 02568
    • /19

      Est $1,423,546

      Not Listed For Sale

      193 Franklin Terrace, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1972
      193 Franklin Terrace, Vineyard Haven, MA 02568

      Last Sold Summary

      • 487 Days On Market

      Last Listing Agent Claire Callagy Wallace & Co. Sotheby's

  • /14

    $685,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 782 Sq Ft

    10 Siloam Ave, Oak Bluffs, MA 02557

    The cottage has been maintained throughout the years, with a new roof in 2015, at which time it was insulated. The original Campground charm has been preserved thoughtfully. New mahogany boards are on front porch and a new paint job on the exterior of the cottage was done last year. The kitchen cabinets have been crafted by a master wood worker and there is a new kitchen floor and appliances.

    Elise LeBovit Gay Head Realty

    10 Siloam Ave, Oak Bluffs, MA 02557
  • /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 $940,668

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    4 Quail Run Unit 7, Oak Bluffs, MA 02557
    • /45

      Est $1,526,935

      Not Listed For Sale

      140 Tashmoo Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,096 Sq Ft
      • Built 1993
      140 Tashmoo Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

  • /11

    $3,495,000

    • Land
    • 11.39 Acres
    • $306,848 per Acre

    0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539

    CHAPPAQUIDDICK - Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to 1⁄2 mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding, and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your

    Katherine Donahue Sandpiper Realty

    0 Pocha Road Extension Unit 1.1,1.2 43325, 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
    • /22

      Est $1,256,505

      Not Listed For Sale

      110 Daggett Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,650 Sq Ft
      • Built 1921
      110 Daggett Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 106 Days On Market

      Last Listing Agent Kate Burnside Portfolio Properties

  • /65

    $45,000,000

    • 7 Beds
    • 13 Baths
    • 14,780 Sq Ft

    18 Point Inner Way, Chilmark, MA 02535

    A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the

    Alyssa Halisky Wallace & Co. Sotheby's

    18 Point Inner Way, Chilmark, MA 02535
  • /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 $808,156

    Last Listing Agent Stephanie Roache Donnelly + Co.

    24 School St, Oak Bluffs, MA 02557
    • /2

      Est $1,198,771

      Not Listed For Sale

      284 Daggett Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1970
      284 Daggett Ave, Vineyard Haven, MA 02568

  • /10

    $4,800,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,816 Sq Ft

    7 Marthas Rd, Edgartown, MA 02539

    Welcome to this coastal chic farmhouse set in the heart of Katama, a few blocks from the Field Club, close to SOUTH BEACH and close to Edgartown Village. To be built is a four bedroom en-suite home with a heated saltwater POOL. This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home offers an inviting covered porch with free standing columns, a granite entry

    Michele Casavant Vineyard Village Realty

    7 Marthas Rd, Edgartown, MA 02539
  • /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

    Current Estimated Value $2,395,392

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

    209 Chappaquiddick Rd, Edgartown, MA 02539
    • /44

      Est $1,411,081

      Not Listed For Sale

      4 Lady Slipper Way, Vineyard Haven, MA 02568

      • 5 Beds
      • 3 Baths
      • 1,781 Sq Ft
      • Built 1997
      4 Lady Slipper Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 101 Days On Market

      Last Listing Agent June Flake Viewpoints

  • /40

    $1,625,000

    $70K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,342 Sq Ft

    58 Road To the Plains, Edgartown, MA 02539

    Turnkey Katama Retreat – Welcome to this beautifully appointed, fully furnished home, offering the perfect blend of relaxed coastal living and effortless ownership. With a strong rental history and thoughtful upgrades throughout, this property is an exceptional opportunity as a year-round residence, vacation escape, or income-producing investment. At the heart of the outdoor experience is a

    Stephanie Roache Donnelly + Co

    58 Road To the Plains, Edgartown, MA 02539
  • /48

    $4,750,000

    Sold Nov 21, 2025

    36 Crocker Dr, Edgartown, MA 02539

    • 3 Beds
    • 3.5 Baths
    • 4,131 Sq Ft
    • Built 2024

    Last Sold Summary

    • 14% Below List Price
    • $1,150/SF
    • 61 Days On Market

    Current Estimated Value $5,013,862

    Last Listing Agent Stephanie Roache Donnelly + Co

    36 Crocker Dr, Edgartown, MA 02539
    • /31

      Est $1,338,607

      Not Listed For Sale

      191 Spring Hill Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 2,292 Sq Ft
      • Built 1992
      191 Spring Hill Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

  • /20

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft

    10 Abels Neck Rd, Chilmark, MA 02535

    Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway

    Julianna Flanders Flanders Real Estate

    10 Abels Neck Rd, Chilmark, MA 02535
  • /49

    $1,650,000

    Sold Apr 28, 2026

    39 Iron Hill Rd, Oak Bluffs, MA 02557

    • 5 Beds
    • 5.5 Baths
    • 4,334 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $381/SF
    • 2 Days On Market

    Current Estimated Value $1,915,651

    Last Listing Agent Wendy Harman Compass | Point B

    39 Iron Hill Rd, Oak Bluffs, MA 02557
    • /19

      Est $1,081,585

      Not Listed For Sale

      160 Spring Hill Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,235 Sq Ft
      • Built 1983
      160 Spring Hill Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Rene Jackson Island Real Estate

  • /33

    $1,425,000

    $475K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,056 Sq Ft

    20 Brook Hollow Rd, Vineyard Haven, MA 02568

    This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

    Jim Feiner Feiner Real Estate

    20 Brook Hollow Rd, Vineyard Haven, MA 02568
  • /39

    $3,515,000

    Sold Aug 18, 2025

    7 Whistling Swan Cir, Edgartown, MA 02539

    • 5 Beds
    • 4.5 Baths
    • 4,218 Sq Ft
    • Built 2010

    Last Sold Summary

    • 4% Below List Price
    • $833/SF
    • 60 Days On Market

    Current Estimated Value $3,597,699

    Last Listing Agent Jarrett Hurwitz Keller Williams Realty

    7 Whistling Swan Cir, Edgartown, MA 02539
    • /72

      Est $1,198,382

      Not Listed For Sale

      18 Goah Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,861 Sq Ft
      • Built 1998
      18 Goah Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 135 Days On Market

      Last Listing Agent Stephanie Burke Portfolio Properties

  • /45

    $1,765,000

    • 2 Beds
    • 2 Baths
    • 890 Sq Ft

    2 Great Rock Rd, Oak Bluffs, MA 02568

    Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property

    Susan Lemoie-Zarba Premier Properties

    2 Great Rock Rd, Oak Bluffs, MA 02568
  • /3

    $5,750,000

    Sold Apr 10, 2026

    23 Chockers Ln, Chilmark, MA 02535

    • 2 Beds
    • 1.5 Baths
    • 1,446 Sq Ft
    • Built 1993

    Last Sold Summary

    • $3,976/SF
    • 0 Days On Market

    Current Estimated Value $5,418,415

    Last Listing Agent Julianna Flanders Flanders Real Estate

    23 Chockers Ln, Chilmark, MA 02535

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