19,907

Dukes County, MA Homes

Section Image
    • /2

      Est $2,294,692

      Not Listed For Sale

      5 Marsh Hawk Cir, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,139 Sq Ft
      • Built 1983
      5 Marsh Hawk Cir, Edgartown, MA 02539

  • /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
  • /46

    $6,200,000

    Sold Jul 03, 2025

    79 Rachels Way, Vineyard Haven, MA 02568

    • 4 Beds
    • 4 Baths
    • 3,278 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $1,891/SF
    • 0 Days On Market

    Current Estimated Value $6,593,306

    Last Listing Agent Jennifer O'hanlon Compass LLC

    79 Rachels Way, Vineyard Haven, MA 02568
    • /34

      Not Listed For Sale

      391 Middle Rd, Chilmark, MA 02535

      • 6 Beds
      • 4.5 Baths
      • 3,859 Sq Ft
      • Built 1941
      391 Middle Rd, Chilmark, MA 02535

      Last Sold Summary

      • 38 Days On Market

  • /12

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    0 Bayberry Hill Rd Unit 22602271, Gosnold, MA 02713

    Perched high above the harbor on one of New England's most secluded islands, Folly on Bayberry Hill is a classic Cuttyhunk retreat offering exceptional privacy, timeless coastal character, and sweeping panoramic water views.The home's elevated setting creates a remarkable sense of openness, light, and connection to the surrounding coastal landscape. Inside, approximately 1,472 square feet of

    Slater Anderson LandVest, Inc.

    0 Bayberry Hill Rd Unit 22602271, Gosnold, MA 02713
  • /7

    $600,000

    Sold Nov 04, 2025

    10 Putnam Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • Built 1972

    Last Sold Summary

    • 22% Below List Price
    • $514/SF
    • 39 Days On Market

    Current Estimated Value $716,343

    Last Listing Agent Kathleen Dawson Donnelly + Co.

    10 Putnam Way, Vineyard Haven, MA 02568
    • /41

      Est $2,293,784

      Not Listed For Sale

      70 Marthas Rd, Edgartown, MA 02539

      • 3 Beds
      • 2.5 Baths
      • 1,875 Sq Ft
      • Built 2000
      70 Marthas Rd, Edgartown, MA 02539

      Last Sold Summary

      • 3 Days On Market

  • /8

    $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
  • /2

    $1,500,000

    Sold Aug 13, 2025

    82 Christiantown Rd Unit R, West Tisbury, MA 02575

    • Land
    • 7.42 Acres
    • $202,156 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    82 Christiantown Rd Unit R, West Tisbury, MA 02575
    • /24

      Est $1,513,502

      Not Listed For Sale

      92 Winyah Cir, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 2,625 Sq Ft
      • Built 1983
      92 Winyah Cir, Vineyard Haven, MA 02568

      Last Sold Summary

      • 78 Days On Market

  • /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
  • /20

    $1,225,000

    Sold Mar 16, 2026

    344 Greenwood Ave, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1981

    Last Sold Summary

    • 6% Below List Price
    • $782/SF
    • 75 Days On Market

    Current Estimated Value $1,221,971

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    344 Greenwood Ave, Vineyard Haven, MA 02568
    • /34

      Est $1,879,379

      Not Listed For Sale

      21 Llewellyn Way, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 1,450 Sq Ft
      • Built 1988
      21 Llewellyn Way, Edgartown, MA 02539

      Last Sold Summary

      • 31 Days On Market

  • /15

    $1,495,000

    $2M PRICE DROP
    • Land
    • 3.01 Acres
    • $496,678 per Acre

    11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568

    Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

    Cassie Courtney Wallace & Co. Sotheby's

    11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568
  • /41

    $1,900,000

    Sold May 01, 2026

    36 Smith Hollow Dr, Edgartown, MA 02539

    • 5 Beds
    • 2.5 Baths
    • 2,836 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $670/SF
    • 172 Days On Market

    Current Estimated Value $1,933,060

    Last Listing Agent Katherine Donahue Sandpiper Realty

    36 Smith Hollow Dr, Edgartown, MA 02539
    • /2

      Est $1,308,171

      Not Listed For Sale

      201 Spring St, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1976
      201 Spring St, Vineyard Haven, MA 02568

  • /12

    $4,800,000

    • 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
  • /27

    $1,735,000

    Sold Sep 29, 2025

    56 Bridle Path Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 4 Baths
    • 2,526 Sq Ft
    • Built 1996

    Last Sold Summary

    • 13% Below List Price
    • $687/SF
    • 2 Days On Market

    Current Estimated Value $2,197,661

    Last Listing Agent Tina Miller Donnelly + Co.

    56 Bridle Path Rd, Vineyard Haven, MA 02568
    • /16

      Est $1,848,443

      Not Listed For Sale

      8 Marsh Hawk Cir, Edgartown, MA 02539

      • 5 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1980
      8 Marsh Hawk Cir, Edgartown, MA 02539

      Last Sold Summary

      • 27 Days On Market

  • /44

    $7,200,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,389 Sq Ft

    2 Noras Ln, Edgartown, MA 02539

    Located in the highly sought-after Nora's Meadow in Edgartown neighborhood, this exceptional coastal property offers the rare combination of privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.8 beautifully landscaped acres, this custom-built home, completed in 2014, features over 4,000 square feet of thoughtfully designed living space

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    2 Noras Ln, Edgartown, MA 02539
  • /15

    $1,000,000

    Sold May 13, 2026

    140 Midland Ave, Tisbury, MA 02568

    • 4 Beds
    • 4 Baths
    • 1,999 Sq Ft
    • Built 1974

    Last Sold Summary

    • 33% Below List Price
    • $500/SF
    • 2 Days On Market

    Last Listing Agent Tina Miller Donnelly + Co

    140 Midland Ave, Tisbury, MA 02568
    • /2

      Not Listed For Sale

      39 Sarita Walker Rd, Vineyard Haven, MA 02568

      • 6 Beds
      • 5 Baths
      • 3,540 Sq Ft
      • Built 1830
      39 Sarita Walker Rd, Vineyard Haven, MA 02568

  • /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
  • /42

    $2,900,000

    Sold Jul 03, 2025

    67 Hidden Village Rd, Vineyard Haven, MA 02568

    • 7 Beds
    • 5.5 Baths
    • 4,476 Sq Ft
    • Built 1997

    Last Sold Summary

    • 24% Below List Price
    • $648/SF
    • 347 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    67 Hidden Village Rd, Vineyard Haven, MA 02568
    • /42

      Est $1,939,677

      Not Listed For Sale

      44 Music St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,172 Sq Ft
      • Built 1984
      44 Music St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 66 Days On Market

  • /39

    $7,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535
  • /28

    $1,400,000

    Sold Nov 26, 2025

    5 Scottys Ln, Vineyard Haven, MA 02568

    • 4 Beds
    • 1.5 Baths
    • 1,592 Sq Ft
    • Built 1968

    Last Sold Summary

    • 22% Below List Price
    • $879/SF
    • 126 Days On Market

    Current Estimated Value $1,620,913

    Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    5 Scottys Ln, Vineyard Haven, MA 02568
    • /23

      Est $1,998,751

      Not Listed For Sale

      50 Campbell Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,370 Sq Ft
      • Built 1994
      50 Campbell Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16 Days On Market

  • /33

    $1,575,000

    $325K 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
  • /34

    $3,746,925

    Sold Nov 14, 2025

    39 Sengekontacket Rd, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 2,861 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $1,310/SF
    • 114 Days On Market

    Current Estimated Value $3,690,250

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    39 Sengekontacket Rd, Edgartown, MA 02539
    • /6

      Est $2,952,719

      Not Listed For Sale

      71 Runner Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,935 Sq Ft
      • Built 1982
      71 Runner Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /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
  • /2

    $24,000,000

    Sold Jan 28, 2026

    177 Katama Rd, Edgartown, MA 02539

    • 5 Beds
    • 4 Baths
    • 3,728 Sq Ft
    • Built 1900

    Last Sold Summary

    • $6,438/SF
    • 0 Days On Market

    Current Estimated Value $11,812,786

    Last Listing Agent Thomas Leclair Landvest MV

    177 Katama Rd, Edgartown, MA 02539
    • /26

      Not Listed For Sale

      137 Charles Neck Way, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 2,610 Sq Ft
      • Built 1986
      137 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 8 Days On Market

  • /6

    $995,000

    $105K PRICE DROP
    • Land
    • 43,472 Sq Ft
    • $996,994 per Acre

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539

    Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist the buyer with costs associated with the design, permitting, and installation of the septic system. The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently

    Casandra Hyland Sandpiper Realty

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
  • /17

    $700,000

    Sold Jun 20, 2025

    2 Fisk Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 725 Sq Ft
    • Built 1870

    Last Sold Summary

    • 7% Below List Price
    • $966/SF
    • 111 Days On Market

    Current Estimated Value $735,366

    Last Listing Agent Julie Walker Century 21 North East

    2 Fisk Ave, Oak Bluffs, MA 02557
    • /35

      Est $1,768,114

      Not Listed For Sale

      55 Charles Neck Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,654 Sq Ft
      • Built 1984
      55 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 182 Days On Market

  • /38

    $12,500,000

    • 5 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    18 Spruce Gate Rd, Chilmark, MA 02535

    Welcome to an extraordinary coastal retreat within the exclusive gates of Squibnocket Farm, a 450+ acre private community offering access to over two miles of oceanfront, pond frontage, and conservation land. Designed and built by Soikkeli & Company, this elegant home blends timeless New England farmhouse architecture with refined modern luxury. The chef’s kitchen features soapstone countertops,

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    18 Spruce Gate Rd, Chilmark, MA 02535
  • /37

    $1,705,000

    Sold Mar 24, 2026

    2 Farm Path, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft
    • Built 1992

    Last Sold Summary

    • 15% Below List Price
    • $558/SF
    • 347 Days On Market

    Current Estimated Value $1,688,778

    Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
    • /2

      Est $1,335,049

      Not Listed For Sale

      16 Elias Ln, Vineyard Haven, MA 02568

      • 1 Bed
      • 2 Baths
      • 856 Sq Ft
      • Built 1993
      16 Elias Ln, Vineyard Haven, MA 02568

Showing Results 441 - 480, Page 12 of 18

How to Buy a Home How to Finance a Home How to Sell a Home