19,348

Dukes County, MA Homes

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  • /6

    $3,750,000

    • Land
    • 3.6 Acres
    • $1,041,667 per Acre

    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575

    Set on a picturesque peninsula along Tisbury Great Pond, this exceptional pondfront parcel offers a rare opportunity to own a piece of Martha's Vineyard's rural landscape. Currently used for equestrian activities, the expansive open acreage is nestled in one of the Island's most beautiful and unspoiled settings, evoking West Tisbury's rich agricultural heritage. This property is a blank slate,

    Meg Bodnar Tea Lane Associates

    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
  • /30

    $20,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,226 Sq Ft
    • House for Rent

    54 Schoolhouse Road Ed330, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny

    Karen Overtoom Karen M. Overtoom R.E.

    54 Schoolhouse Road Ed330, Edgartown, MA 02539
  • /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
    • /37

      Est $1,890,967

      Not Listed For Sale

      3 Duncan Close, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,668 Sq Ft
      • Built 1979
      3 Duncan Close, Edgartown, MA 02539

      Last Sold Summary

      • 353 Days On Market

      Last Listing Agent Wendy Harman Compass | Point B

  • /7

    $2,850,000

    Pending
    • Land
    • 1.52 Acres
    • $1,881,064 per Acre

    39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539

    SPECTACULAR LOCATION! Build Your Katama Dream. Set in one of Martha’s Vineyard’s most sought-after locations, this newly created 1.5-acre parcel offers a rare opportunity to build your custom island retreat in the heart of Katama. Perfectly sited near the pristine shores of South Beach, the level and conforming R60 lot provides endless potential for a main residence and an outdoor oasis designed

    Fran Agnoli The Agency

    39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539
  • /40

    $32,500 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,222 Sq Ft
    • House for Rent

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

    Karen Overtoom Karen M. Overtoom R.E.

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, 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
    • /34

      Est $2,353,801

      Not Listed For Sale

      338 Bigelow Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,783 Sq Ft
      • Built 1978
      338 Bigelow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Emily Flake Viewpoints; Bobbi Flake Reed, Inc.

  • /2

    $425,000

    • Land
    • 7,840 Sq Ft
    • $2,361,111 per Acre

    0 Heather Ln Unit 56, Oak Bluffs, MA 02568

    Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

    Jennifer DaSilva Compass | Point B

    0 Heather Ln Unit 56, Oak Bluffs, 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
    • /34

      Est $4,053,057

      Not Listed For Sale

      26 Morse St, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,446 Sq Ft
      • Built 1840
      26 Morse St, Edgartown, MA 02539

      Last Sold Summary

      • 984 Days On Market

      Last Listing Agent Stephanie Burke Portfolio Properties

  • /33

    $1,400,000

    • 5 Beds
    • 2.5 Baths
    • 2,083 Sq Ft

    5 Paula Ave, Vineyard Haven, MA 02568

    Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert's Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert's Cove Beach, this well-positioned property offers the perfect blend of convenience, privacy, and potential. Spanning three levels, this five-bedroom,

    Emma Bryant Studio Realty

    5 Paula Ave, Vineyard Haven, MA 02568
  • /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
    • /17

      Est $652,634

      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

      • 30 Days On Market

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /37

    $3,750,000

    • 4 Beds
    • 3 Baths
    • 2,204 Sq Ft

    9 Weston Ave, Oak Bluffs, MA 02568

    This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor

    Gerrett Conover Landvest MV

    9 Weston Ave, Oak Bluffs, 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
    • /29

      Est $2,184,494

      Not Listed For Sale

      21 William St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,378 Sq Ft
      • Built 1928
      21 William St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Laura Finney Wallace & Co. Sotheby's

  • /21

    $1,975,000

    • 2 Beds
    • 2 Baths
    • 730 Sq Ft

    131 N Water St Unit 94, Edgartown, MA 02539

    LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730± sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services.

    Mitzi Lawlor Corcoran Property Advisors

    131 N Water St Unit 94, 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
    • /29

      Est $1,464,313

      Not Listed For Sale

      87 Schoolhouse Rd, Edgartown, MA 02539

      • 2 Beds
      • 2.5 Baths
      • 1,119 Sq Ft
      • Built 1983
      87 Schoolhouse Rd, Edgartown, MA 02539

      Last Sold Summary

      • 123 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /13

    $1,575,000

    $70K PRICE DROP
    • Land
    • 3.32 Acres
    • $474,398 per Acre

    26 Flint Hill Rd, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

    Dawn Bellante Sandpiper Realty, Inc.

    26 Flint Hill Rd, West Tisbury, MA 02575
  • /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
    • /32

      Est $1,290,072

      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

      • 167 Days On Market

      Last Listing Agent Neal Stiller Cronigs Real Estate

  • /26

    $32,500,000

    Pending
    • 9 Beds
    • 12 Baths
    • 7,190 Sq Ft

    61 Butlers Cove, Edgartown, MA 02539

    Beach Farm is an extraordinary 18.6-acre waterfront estate offering exceptional privacy, 1,700 feet of water frontage, sweeping Atlantic views, two private beaches, and a rare walking path to the pristine South Shore. Set within the storied 200-acre Herring Creek Farm, a coastal enclave surrounding a working farm with barns, horses, sheep, and open meadows, Beach Farm is just a short bike ride to

    Brian Dougherty Corcoran Property Advisors

    61 Butlers Cove, 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
    • /35

      Est $3,406,893

      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

      • 35 Days On Market

      Last Listing Agent Kathryn Tate Kathryn Tate Gothard

  • /33

    $1,599,000

    • 3 Beds
    • 2.5 Baths
    • 1,645 Sq Ft

    7 Ploughshare Ln, Oak Bluffs, MA 02557

    Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

    Emma Kennedy Sandpiper Realty, Inc.

    7 Ploughshare Ln, Oak Bluffs, MA 02557
  • /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
    • /35

      Est $2,161,383

      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

      • 47 Days On Market

      Last Listing Agent Wendy Harman Compass

  • /22

    $3,995,000

    $700K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,816 Sq Ft

    30 Water Gate Rd, Vineyard Haven, MA 02568

    Set privately in one of Vineyard Haven's most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for gathering and quiet retreat, with an effortless indoor-outdoor flow. Bedrooms are thoughtfully arranged in separate wings, with a

    Peyton Wallace Studio Realty LLC

    30 Water Gate Rd, Vineyard Haven, MA 02568
  • /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
    • /41

      Est $2,056,407

      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

      • 0 Days On Market

      Last Listing Agent Heidi Vanderhoop Tea Lane Associates

  • /42

    $3,225,000

    • 3 Beds
    • 4.5 Baths
    • 3,219 Sq Ft

    8 Woodhaven Dr, Edgartown, MA 02539

    Hidden behind a veil of privacy on a generous coastal sanctuary, an extraordinary property waits to be discovered. This custom masterpiece blends timeless architecture with a modern, elusive sophistication, offering comfortable finished living space within an impressive total structure. Cross the threshold onto rich hardwood floors where light dances beneath a dramatic cathedral ceiling, drawing

    Jennifer B. DaSilva Compass

    8 Woodhaven Dr, 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
    • /30

      Est $2,088,402

      Not Listed For Sale

      55 Old Purchase Rd, Edgartown, MA 02539

      • 5 Beds
      • 3.5 Baths
      • 2,779 Sq Ft
      • Built 1988
      55 Old Purchase Rd, Edgartown, MA 02539

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /48

    $5,850,000

    Pending
    • 6 Beds
    • 6.5 Baths
    • 3,608 Sq Ft

    9 Ridge Hill Rd, Chilmark, MA 02535

    Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn and 16' x 40' swimming pool. This thoughtfully designed post and beam main home was featured in

    Alexis Holden Tea Lane Associates

    9 Ridge Hill Rd, Chilmark, MA 02535
  • /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

      Est $1,033,127

      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

      • 102 Days On Market

      Last Listing Agent Jennifer B. DaSilva Compass

  • /42

    $4,600,000

    $350K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 3,998 Sq Ft

    15 Tamarack Ln, Oak Bluffs, MA 02557

    Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic

    Stephanie Roache Donnelly + Co.

    15 Tamarack Ln, Oak Bluffs, MA 02557
  • /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

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