19,907

Dukes County, MA Homes

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  • /42

    $3,199,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
  • /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 $1,803,134

    Last Listing Agent LINK Email Cache LINK

    14 Chapman Ave, Oak Bluffs, MA 02557
    • /19

      Est $1,251,263

      Not Listed For Sale

      31 Davis St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,945 Sq Ft
      • Built 1966
      31 Davis St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 5 Days On Market

  • /65

    $3,250,000

    • 4 Beds
    • 3 Baths
    • 2,348 Sq Ft

    82 Oyster Pond Rd, Edgartown, MA 02539

    A truly rare offering on Oyster Pond Rd. This property offer rights to boating and swimming in the pond plus a rare easement to access “The Barrier Beach", on the south shore. Access to the south beach is by boating down Oyster Pond.This beach access is a spectacular addition to this property. The land is 4.4 acres, very quiet and bordered by exceptional homes. Privacy abounds. This contemporary

    Neal Stiller Cronigs Real Estate

    82 Oyster Pond Rd, Edgartown, MA 02539
  • /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 $836,311

    Last Listing Agent Rene Ben David Ocean Park Realty Inc

    21 Norris Ave, Vineyard Haven, MA 02568
    • /25

      Est $4,671,366

      Not Listed For Sale

      36 Burts Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 7 Baths
      • 4,000 Sq Ft
      • Built 2004
      36 Burts Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19 Days On Market

  • /38

    $1,495,000

    Under Contract
    • 1 Bed
    • 2.5 Baths
    • 1,254 Sq Ft

    20 Union St Unit C, Tisbury, MA 02568

    Welcome to 20 Union Court, Unit C at the Old Stone Bank Condominiums - a unique community in the heart of downtown Vineyard Haven. This two-level condo offers a truly special Vineyard lifestyle. Enter through the inviting porch into an open floor plan filled with character, thoughtful details, and sun-lit rooms that create a warm and welcoming atmosphere throughout. This home features a

    Michele Moore Island Real Estate

    20 Union St Unit C, Tisbury, MA 02568
  • /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 $956,706

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    4 Quail Run Unit 7, Oak Bluffs, MA 02557
    • /2

      Est $1,839,785

      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

      • 0 Days On Market

  • /20

    $1,550,000

    $100K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 716 Sq Ft

    46 Tiercel Ln, Chilmark, MA 02535

    Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort and

    Stacy Ickes Donnelly + Co

    46 Tiercel Ln, Chilmark, MA 02535
  • /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
    • /2

      Est $1,859,334

      Not Listed For Sale

      201 Lagoon Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,676 Sq Ft
      • Built 1870
      201 Lagoon Pond Rd, Vineyard Haven, MA 02568

  • /37

    $7,950,000

    • 5 Beds
    • 7 Baths
    • 4,531 Sq Ft

    85 Reservoir Rd, Vineyard Haven, MA 02568

    Nestled within Seven Gates Farm, one of Martha’s Vineyard’s most storied and scenic communities, this 26.5-acre estate features a beautifully renovated farmhouse blending modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property also includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    85 Reservoir Rd, Vineyard Haven, MA 02568
  • /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 $786,677

    Last Listing Agent Stephanie Roache Donnelly + Co.

    24 School St, Oak Bluffs, MA 02557
    • /25

      Est $1,138,635

      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

      • 115 Days On Market

  • /26

    $3,100,000

    • 1 Bed
    • 1 Bath
    • 1,250 Sq Ft

    114 Meeting House Way, Edgartown, MA 02539

    3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach

    Rose Ryley Wallace & Co. Sotheby's International Realty

    114 Meeting House Way, 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 $2,295,339

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

    209 Chappaquiddick Rd, Edgartown, MA 02539
    • /2

      Est $588,360

      Not Listed For Sale

      92 Rogers Farm Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,189 Sq Ft
      • Built 1900
      92 Rogers Farm Rd, Vineyard Haven, MA 02568

  • /24

    $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
  • /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 $4,705,232

    Last Listing Agent Stephanie Roache Donnelly + Co

    36 Crocker Dr, Edgartown, MA 02539
    • /19

      Est $980,688

      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

      • 83 Days On Market

  • /29

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    13 Young St, Edgartown, MA 02539

    This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an

    Stacy Ickes Donnelly + Co.

    13 Young St, Edgartown, MA 02539
  • /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 $2,066,005

    Last Listing Agent Wendy Harman Compass | Point B

    39 Iron Hill Rd, Oak Bluffs, MA 02557
    • /23

      Est $1,195,153

      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

      • 96 Days On Market

  • /38

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 1,714 Sq Ft

    116 Franklin Terrace, Vineyard Haven, MA 02568

    Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full

    Pricila Ray Keller Williams Realty

    116 Franklin Terrace, Vineyard Haven, MA 02568
  • /44

    $37,000,000

    Sold Jul 10, 2025

    41 Cobbs Hill Rd, Chilmark, MA 02535

    • 8 Beds
    • 5.5 Baths
    • 7,846 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $4,716/SF
    • 39 Days On Market

    Last Listing Agent Brian Dougherty Corcoran Property Advisors

    41 Cobbs Hill Rd, Chilmark, MA 02535
    • /24

      Est $1,840,380

      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

      • 88 Days On Market

  • /34

    $11,250,000

    • 7 Beds
    • 8 Baths
    • 10,142 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. This is 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 a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized

    Gerrett Conover Landvest MV

    14 Trapps Pond Rd, Edgartown, MA 02539
  • /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 $3,515,006

    Last Listing Agent Jarrett Hurwitz Keller Williams Realty

    7 Whistling Swan Cir, Edgartown, MA 02539
    • /2

      Est $1,263,966

      Not Listed For Sale

      26 Daggett Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,308 Sq Ft
      • Built 1904
      26 Daggett Ave, Vineyard Haven, MA 02568

  • /33

    $3,750,000

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    28 Beach Rd, Oak Bluffs, MA 02557

    Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

    Scott Lewis Lewis Real Estate Services, LLC

    28 Beach Rd, Oak Bluffs, MA 02557
  • /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 $5,280,715

    Last Listing Agent Julianna Flanders Flanders Real Estate

    23 Chockers Ln, Chilmark, MA 02535
    • /2

      Not Listed For Sale

      301 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 1,632 Sq Ft
      • Built 1900
      301 Main St, Vineyard Haven, MA 02568

  • /2

    $3,000,000

    Pending
    • Land
    • 5 Acres
    • $600,000 per Acre

    15 & 27 Pennywise Path Unit 33, Edgartown, MA 02539

    PRIME 5-ACRE LOT - R20 ZONE EDGARTOWN Introducing a rare opportunity to own a piece of the island (currently two parcels) close to all Edgartown has to offer. This spectacular level lot is situated along Edgartown Road and provides the perfect setting to create a private retreat or a potential subdivision. The property borders the Triangle area of Edgartown, with ease of access to public

    John O'Connell Portfolio Properties

    15 & 27 Pennywise Path Unit 33, Edgartown, MA 02539
  • /20

    $821,000

    Sold Jun 17, 2025

    168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

    • Land
    • 1.4 Acres
    • $586,429 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 0 Days On Market

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
    • /2

      Est $2,192,643

      Not Listed For Sale

      51 Hatch Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 2,066 Sq Ft
      • Built 1910
      51 Hatch Rd, Vineyard Haven, MA 02568

  • /32

    $2,995,000

    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    300 N Road 18 Belhaven Way, Chilmark, MA 02535

    This Chilmark home is one-of-a-kind - a warm, charming hideaway set on 4.4 spectacular acres just off North Road. At the top of a shady driveway you are met by stone walls so typical of Chilmark from a bygone era. You enter a courtyard through cedar gates where you find beautifully tended flower beds. The porch is the ideal location for you to enjoy the private, peaceful courtyard. Immediately

    Bonnie Pierce Wallace & Co. Sotheby's

    300 N Road 18 Belhaven Way, Chilmark, MA 02535
  • /37

    $3,600,000

    Sold Feb 12, 2026

    8 High St, Edgartown, MA 02539

    • 5 Beds
    • 4 Baths
    • 3,840 Sq Ft
    • Built 1910

    Last Sold Summary

    • 16% Below List Price
    • $938/SF
    • 62 Days On Market

    Current Estimated Value $3,937,405

    Last Listing Agent Valene Pires The Agency

    8 High St, Edgartown, MA 02539
    • /2

      Est $1,031,862

      Not Listed For Sale

      50 Old Lighthouse Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 961 Sq Ft
      • Built 1961
      50 Old Lighthouse Rd, Vineyard Haven, MA 02568

  • /4

    $809,000

    • Land
    • 16,901 Sq Ft
    • $2,085,052 per Acre

    7 Highland Ave Unit 119, Vineyard Haven, MA 02568

    Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

    Shera Toledo eXp Realty

    7 Highland Ave Unit 119, Vineyard Haven, MA 02568

Showing Results 601 - 640, Page 16 of 18

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