20,063

Dukes County, MA Homes

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  • /2

    $1,000,000 Sold Oct 21, 2025

    32 Pine St, Edgartown, MA 02539

    • 3 Beds
    • 1 Bath
    • 979 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,021/SF
    • 0 Days On Market

    Current Estimated Value $1,147,712

    Last Listing Agent LINK Email Cache LINK

    32 Pine St, Edgartown, MA 02539
    • /17

      Est $566,007 Not Listed For Sale

      15 Walker Way, Vineyard Haven, MA 02568

      • 1 Bed
      • 1 Bath
      • 432 Sq Ft
      • Built 1940
      15 Walker Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 8% Above List Price
      • $1,215/SF
      • 30 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /12

    $1,495,000

    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

    Stephanie Burke Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • /69

    $1,160,000 Sold Jan 05, 2026

    208 Irenes Way, Tisbury, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,961 Sq Ft
    • Built 2005

    Last Sold Summary

    • 24% Below List Price
    • $392/SF
    • 168 Days On Market

    Current Estimated Value $1,261,854

    Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

    208 Irenes Way, Tisbury, MA 02568
    • /8

      Not Listed For Sale

      16 Forever Wild Way, Edgartown, MA 02539

      • 2 Beds
      • Built 1930
      16 Forever Wild Way, Edgartown, MA 02539

      Last Sold Summary

      • $4,623/SF
      • 0 Days On Market

      Last Sold Price $3,125,000

      Last Listing Agent Julia Smith Donnelly + Co

  • /8

    $3,495,000

    • Land
    • 11.49 Acres
    • $304,178 per Acre

    0 Pocha Rd, 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 backyard.

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    0 Pocha Rd, Edgartown, MA 02539
  • /22

    $1,000,000 Sold Jul 31, 2025

    130 Wing Rd, Oak Bluffs, MA 02557

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1960

    Last Sold Summary

    • 10% Below List Price
    • $1,302/SF
    • 96 Days On Market

    Current Estimated Value $943,407

    Last Listing Agent Lynn Buder Sandpiper Realty Inc

    130 Wing Rd, Oak Bluffs, MA 02557
    • /12

      Not Listed For Sale

      9 Dunes Rd, Edgartown, MA 02539

      • 6 Beds
      • 4.5 Baths
      • 2,892 Sq Ft
      • Built 1981
      9 Dunes Rd, Edgartown, MA 02539

      Last Sold Summary

      • $1,335/SF
      • 0 Days On Market

      Last Sold Price $3,860,000

      Last Listing Agent Jarrett Hurwitz Keller Williams Realty

  • /54

    $1,830,000

    • 4 Beds
    • 4 Baths
    • 1,600 Sq Ft

    12 & 14 Maple Ave, Oak Bluffs, MA 02557

    Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

    Leslie Floyd Portfolio Properties

    12 & 14 Maple Ave, Oak Bluffs, MA 02557
  • /33

    $2,637,500 Sold Dec 12, 2025

    36 Tashmoo Ave, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,770 Sq Ft
    • Built 1888

    Last Sold Summary

    • 20% Below List Price
    • $952/SF
    • 355 Days On Market

    Current Estimated Value $2,754,324

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

    36 Tashmoo Ave, Vineyard Haven, MA 02568
    • /32

      Est $1,268,277 Not Listed For Sale

      58 Hagerty Dr, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,118 Sq Ft
      • Built 1983
      58 Hagerty Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17% Above List Price
      • $970/SF
      • 167 Days On Market

      Last Sold Price $1,085,000

      Last Listing Agent Neal Stiller Cronigs Real Estate

  • /4

    $1,025,000

    • Land
    • 1 Acre
    • $1,025,000 per Acre

    25 Coffins Field Rd, Edgartown, MA 02539

    Per the BOH, this property can accommodate a 3 bedroom home and with appropriate permitting may allow for an additional/separate structure such as a garage or studioProperty is not serviced by a well or septic system. Buyer is responsible for obtaining permits and installation.Association Dues $650.00

    Casandra Hyland Sandpiper Realty, Inc.

    25 Coffins Field Rd, Edgartown, MA 02539
  • /20

    $1,150,000 Sold Jun 13, 2025

    46 Old Coach Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,374 Sq Ft
    • Built 1981

    Last Sold Summary

    • 10% Below List Price
    • $837/SF
    • 43 Days On Market

    Current Estimated Value $1,214,339

    Last Listing Agent Lisa Gilberto C McManus Realty Group

    46 Old Coach Rd, Vineyard Haven, MA 02568
    • /35

      Est $3,349,419 Not Listed For Sale

      5 Hillman Dr, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,407 Sq Ft
      • Built 1963
      5 Hillman Dr, Edgartown, MA 02539

      Last Sold Summary

      • 3% Above List Price
      • $1,350/SF
      • 35 Days On Market

      Last Sold Price $3,250,000

      Last Listing Agent Kathryn Tate Kathryn Tate Gothard

  • /30

    $999,000

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

    28 Barling Ave, Vineyard Haven, MA 02568

    Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

    Michael Schweikert Ocean Park Realty Inc

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

    $1,260,000 Sold Nov 03, 2025

    11 Flamingo Dr, Edgartown, MA 02539

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 2002

    Last Sold Summary

    • 16% Below List Price
    • $692/SF
    • 182 Days On Market

    Current Estimated Value $1,265,403

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

    11 Flamingo Dr, Edgartown, MA 02539
    • /35

      Est $1,995,378 Not Listed For Sale

      159 Charles Neck Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,995 Sq Ft
      • Built 2003
      159 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • $1,000/SF
      • 47 Days On Market

      Last Sold Price $1,995,000

      Last Listing Agent Wendy Harman Compass

  • /2

    $12,500,000

    • Land
    • 38 Acres
    • $328,947 per Acre

    2 Old Farms Trail Unit 1, Edgartown, MA 02539

    Thirty-eight (38 acres) of available land in Edgartown! This is a truly extraordinary and increasingly rare opportunity to own thirty-eight (38) acres of contiguous land in Edgartown. Come create a landmark estate or private compound in one of Edgartown’s most sought-after locations. Perfectly positioned between the charm of Edgartown Historic Village and the sweeping sands of South Beach and

    Michele Casavant Vineyard Village Realty

    2 Old Farms Trail Unit 1, Edgartown, MA 02539
  • /17

    $929,000 Sold Aug 18, 2025

    299 Franklin St, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,286 Sq Ft
    • Built 1950

    Last Sold Summary

    • $722/SF
    • 6 Days On Market

    Current Estimated Value $974,887

    Last Listing Agent Lisa Lucier Anchor Realty of MV

    299 Franklin St, Vineyard Haven, MA 02568
    • /41

      Est $1,930,692 Not Listed For Sale

      7 Tar Barrel Rd, Aquinnah, MA 02535

      • 3 Beds
      • 3 Baths
      • 1,803 Sq Ft
      • Built 1998
      7 Tar Barrel Rd, Aquinnah, MA 02535

      Last Sold Summary

      • 7% Above List Price
      • $998/SF
      • 0 Days On Market

      Last Sold Price $1,800,000

      Last Listing Agent Heidi Vanderhoop Tea Lane Associates

  • /25

    $3,200,000

    • Land
    • 19.3 Acres
    • $165,803 per Acre

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

    A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

    Jill Napior Tea Lane Associates

    32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
  • /2

    $900,000 Sold Sep 17, 2025

    45 Quenames Rd Unit 30-02, Chilmark, MA 02535

    • Land
    • 3.05 Acres
    • $295,082 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 83 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    45 Quenames Rd Unit 30-02, Chilmark, MA 02535
    • /22

      Est $1,081,986 Not Listed For Sale

      10 Saddle Club Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,025 Sq Ft
      • Built 1985
      10 Saddle Club Rd, Edgartown, MA 02539

      Last Sold Summary

      • 19% Above List Price
      • $888/SF
      • 102 Days On Market

      Last Sold Price $910,000

      Last Listing Agent Jennifer B. DaSilva Compass

  • /38

    $3,990,000

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

    71 Stoney Hill Rd, Vineyard Haven, MA 02568

    A combination of luxury, comfort, and natural beauty, this expansive custom, five bedroom, post and beam home is sited on more than eight acres of land, surrounded by acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow from one room to the next, perfect

    Sheila Morse Island Real Estate

    71 Stoney Hill Rd, Vineyard Haven, MA 02568
  • /22

    $1,299,000 Sold Jun 25, 2025

    2 Boylston Dr, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 1984

    Last Sold Summary

    • 13% Below List Price
    • $859/SF
    • 77 Days On Market

    Current Estimated Value $1,303,513

    Last Listing Agent Martha Smith C McManus Realty Group

    2 Boylston Dr, Edgartown, MA 02539
    • /32

      Est $1,114,891 Not Listed For Sale

      10 Elm St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,429 Sq Ft
      • Built 1970
      10 Elm St, Vineyard Haven, MA 02568

      Last Sold Summary

      • $784/SF
      • 35 Days On Market

      Last Sold Price $1,120,000

      Last Listing Agent Christine Rose Martha's Vineyard Island-Wide Realty

  • /35

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    96 Dunham Ave, Vineyard Haven, MA 02568

    This attractive colonial style home is located in a terrific neighborhood. Just a short distance to the center of town with nearly 1/2 acre of rolling treed land. The features include a cathedral ceiling over the kitchen and dining room. A large fireplace highlights the living room. From upstairs you can look over the balcony to the dining area and kitchen below. The first floor bedroom with has

    Peter Cronig Cronigs Real Estate

    96 Dunham Ave, Vineyard Haven, MA 02568
  • /28

    $1,320,000 Sold Aug 29, 2025

    10 Eagles Nest, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Below List Price
    • $910/SF
    • 6 Days On Market

    Current Estimated Value $1,310,929

    Last Listing Agent Jennifer B. DaSilva Compass

    10 Eagles Nest, Edgartown, MA 02539
    • /47

      Est $2,018,961 Not Listed For Sale

      16 Fishermans Knot Rd, Edgartown, MA 02539

      • 3 Beds
      • 3.5 Baths
      • 2,417 Sq Ft
      • Built 2002
      16 Fishermans Knot Rd, Edgartown, MA 02539

      Last Sold Summary

      • 1% Above List Price
      • $827/SF
      • 24 Days On Market

      Last Sold Price $2,000,000

      Last Listing Agent Jennifer DaSilva Compass | Point B

  • /26

    $1,750,000

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

    103 Meadow View Rd, Oak Bluffs, MA 02557

    Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2 1/2 bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. The interior is designed for both comfort and scale. An expansive front living room has soaring

    Alyson Parker Karen M. Overtoom R.E.

    103 Meadow View Rd, Oak Bluffs, MA 02557
  • /2

    $60,000 Sold Jul 01, 2025

    0 North Rd Unit 40 43533, Aquinnah, MA 02535

    • Land
    • 0 Acre

    Last Sold Summary

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

    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    • /30

      Est $1,371,106 Not Listed For Sale

      88 Hopps Farm Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft
      • Built 1992
      88 Hopps Farm Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Above List Price
      • $908/SF
      • 80 Days On Market

      Last Sold Price $1,330,000

      Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

  • /21

    $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
  • /37

    $2,100,000 Sold Aug 27, 2025

    42 Daggett Ave, Vineyard Haven, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 3,310 Sq Ft
    • Built 2009

    Last Sold Summary

    • 4% Below List Price
    • $634/SF
    • 60 Days On Market

    Current Estimated Value $2,299,248

    Last Listing Agent Rene Jackson Island Real Estate

    42 Daggett Ave, Vineyard Haven, MA 02568
    • /22

      Not Listed For Sale

      33 Summer St, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,250 Sq Ft
      • Built 1924
      33 Summer St, Vineyard Haven, MA 02568

      Last Sold Summary

      • $898/SF
      • 19 Days On Market

      Last Sold Price $1,122,000

      Last Listing Agent Emma Kennedy Sandpiper Realty Inc

  • /20

    $640,000

    • 1 Bed
    • 1 Bath
    • 354 Sq Ft

    2 Lincoln Ave, Oak Bluffs, MA 02568

    Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

    Stacy Ickes Donnelly + Co

    2 Lincoln Ave, Oak Bluffs, MA 02568
  • /2

    $3,772,500 Sold May 29, 2025

    3 Tennis Ln, Chilmark, MA 02535

    • 4 Beds
    • 4.5 Baths
    • 3,234 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Below List Price
    • $1,167/SF
    • 0 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    3 Tennis Ln, Chilmark, MA 02535
    • /19

      Est $2,237,838 Not Listed For Sale

      30 Deacon Vincent Way, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,784 Sq Ft
      • Built 2003
      30 Deacon Vincent Way, Edgartown, MA 02539

      Last Sold Summary

      • 7% Above List Price
      • $754/SF
      • 208 Days On Market

      Last Sold Price $2,100,000

      Last Listing Agent Tara Ledden Ledden Properties LLC

  • /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
  • /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

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