19,872

Dukes County, MA Homes

Section Image
    • /2

      Est $1,406,986

      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

      • 6% Below List Price
      • $908/SF
      • Last Sold Price $1,330,000

      Last Listing Agent Emma Bryant Studio Realty

  • /27

    $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
  • /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
    • /29

      Not Listed For Sale

      33 Summer St, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,558 Sq Ft
      • Built 1924
      33 Summer St, Vineyard Haven, MA 02568

      Last Sold Summary

      • $720/SF
      • 192 Days On Market
      • Last Sold Price $1,122,000
      • Mar 15, 2018

      Last Listing Agent Emma Kennedy Sandpiper Realty

  • /26

    $1,750,000

    Pending
    • 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
  • /3

    $1,695,000

    Sold May 30, 2025

    5 Vincent Rd, Vineyard Haven, MA 02568

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1960

    Last Sold Summary

    • $1,308/SF

    Current Estimated Value $1,414,937

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

    5 Vincent Rd, Vineyard Haven, MA 02568
    • /19

      Est $2,438,630

      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

      • 16% Above List Price
      • $754/SF
      • 208 Days On Market
      • Last Sold Price $2,100,000
      • Mar 14, 2025

      Last Listing Agent Tara Ledden Ledden Properties LLC

  • /60

    $5,495,000

    • 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
  • /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 $1,682,487

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    78 Whalers Walk, Edgartown, MA 02539
    • /2

      Est $1,039,258

      Not Listed For Sale

      73 Leonard Cir, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 1980
      73 Leonard Cir, Vineyard Haven, MA 02568

      Last Sold Summary

      • 1% Below List Price
      • $921/SF
      • Last Sold Price $1,050,000

      Last Listing Agent Leslie C. Floyd Portfolio Properties

  • /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
  • /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
    • /16

      Est $1,404,340

      Not Listed For Sale

      44 Jeremiah Rd, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1996
      44 Jeremiah Rd, Edgartown, MA 02539

      Last Sold Summary

      • 6% Above List Price
      • $960/SF
      • 0 Days On Market
      • Last Sold Price $1,325,000
      • Apr 17, 2024

      Last Listing Agent Cassie Courtney 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
  • /5

    $2,995,000

    Sold Sep 04, 2025

    9 Turkeyland Cove Rd, Edgartown, MA 02539

    • Land
    • 3.01 Acres
    • $995,017 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $3,003,621

    Last Listing Agent Wendy Harman Compass

    9 Turkeyland Cove Rd, Edgartown, MA 02539
    • /2

      Est $1,944,974

      Not Listed For Sale

      163 Charles Neck Way, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 2,508 Sq Ft
      • Built 1987
      163 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19% Below List Price
      • $652/SF
      • Last Sold Price $1,635,000

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

  • /26

    $1,850,000

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft

    12 Lobsterville Rd, Aquinnah, MA 02535

    12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

    Tina Palmer Conroy & Company R.E., Inc.

    12 Lobsterville Rd, Aquinnah, MA 02535
  • /20

    $1,000,000

    Sold Dec 12, 2025

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 2001

    Last Sold Summary

    • 9% Below List Price
    • $470/SF
    • 13 Days On Market

    Current Estimated Value $1,166,674

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
    • /30

      Est $2,778,905

      Not Listed For Sale

      23 Alex Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 5 Baths
      • 2,926 Sq Ft
      • Built 2004
      23 Alex Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 1% Above List Price
      • $945/SF
      • 109 Days On Market
      • Last Sold Price $2,765,000
      • Sep 30, 2024

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /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
  • /7

    $2,995,000

    Sold Sep 04, 2025

    9 Turkeyland Cove Rd Unit 10.31430, Edgartown, MA 02539

    • Land
    • 3.01 Acres
    • $995,017 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 389 Days On Market

    Last Listing Agent Wendy Harman Compass | Point B

    9 Turkeyland Cove Rd Unit 10.31430, Edgartown, MA 02539
    • /25

      Not Listed For Sale

      7 Curtis Ln, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,826 Sq Ft
      • Built 1940
      7 Curtis Ln, Edgartown, MA 02539

      Last Sold Summary

      • $964/SF
      • 44 Days On Market
      • Last Sold Price $1,760,000
      • Nov 21, 2023

      Last Listing Agent Jim Joyce Carroll & Vincent R.E.

  • /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
  • /28

    $1,150,000

    Sold May 08, 2026

    18 Windsor Dr, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,294 Sq Ft
    • Built 1981

    Last Sold Summary

    • 15% Above List Price
    • $889/SF
    • 4 Days On Market

    Current Estimated Value $1,064,756

    Last Listing Agent Stephanie Roache Donnelly + Co.

    18 Windsor Dr, Edgartown, MA 02539
    • /20

      Est $1,357,467

      Not Listed For Sale

      225 Longview Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,730 Sq Ft
      • Built 1977
      225 Longview Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 1% Above List Price
      • $780/SF
      • 18 Days On Market
      • Last Sold Price $1,350,000
      • Nov 20, 2023

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /4

    $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
  • /35

    $1,817,500

    Sold Feb 27, 2026

    32 Flamingo Dr, Edgartown, MA 02539

    • 5 Beds
    • 3 Baths
    • 2,432 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $747/SF
    • 251 Days On Market

    Current Estimated Value $1,847,974

    Last Listing Agent Skip Dostal Martha's Vineyard R.E.

    32 Flamingo Dr, Edgartown, MA 02539
    • /2

      Est $2,260,316

      Not Listed For Sale

      59 Field View Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,269 Sq Ft
      • Built 1975
      59 Field View Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Below List Price
      • $673/SF
      • Last Sold Price $2,200,000

      Last Listing Agent Emma Kennedy Sandpiper Realty

  • /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
  • /61

    $1,910,000

    Sold Apr 03, 2026

    28 Pine Tree Ln, Vineyard Haven, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft
    • Built 1974

    Last Sold Summary

    • 15% Below List Price
    • $588/SF
    • 132 Days On Market

    Current Estimated Value $2,233,444

    Last Listing Agent Wendy Harman Compass | Point B

    28 Pine Tree Ln, Vineyard Haven, MA 02568
    • /31

      Est $1,392,196

      Not Listed For Sale

      99 Summer St, Vineyard Haven, MA 02568

      • 6 Beds
      • 4 Baths
      • 2,655 Sq Ft
      • Built 1985
      99 Summer St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 39% Above List Price
      • $377/SF
      • 0 Days On Market
      • Last Sold Price $1,000,000
      • Jun 02, 2023

      Last Listing Agent LINK Email Cache LINK

  • /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
  • /21

    $895,000

    Sold May 13, 2026

    22 Montgomery Square, Oak Bluffs, MA 02557

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

    Last Sold Summary

    • $961/SF
    • 7 Days On Market

    Current Estimated Value $915,681

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    22 Montgomery Square, Oak Bluffs, MA 02557
    • /50

      Not Listed For Sale

      29 Llewellyn Way, Edgartown, MA 02539

      • 5 Beds
      • 6 Baths
      • 5,195 Sq Ft
      • Built 2001
      29 Llewellyn Way, Edgartown, MA 02539

      Last Sold Summary

      • $877/SF
      • 81 Days On Market
      • Last Sold Price $4,555,000
      • Oct 09, 2024

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /5

    $1,025,000

    $75K PRICE DROP
    • Land
    • 43,472 Sq Ft
    • $1,027,054 per Acre

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539

    Per Board of Health approval, this one-acre parcel can support a six-bedroom home. Ideally situated in a centrally located neighborhood, the property offers a rare combination of privacy and convenience. Abutting conservation land, it features a peaceful, natural setting perfect for your future home. Enjoy close proximity to town, beautiful beaches, scenic bike paths, a public gym, veterinary

    Casandra Hyland Sandpiper Realty

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
  • /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 $6,431,280

    Last Listing Agent Jennifer O'hanlon Compass LLC

    79 Rachels Way, Vineyard Haven, MA 02568
    • /42

      Not Listed For Sale

      49 William St, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 3,752 Sq Ft
      • Built 1836
      49 William St, Vineyard Haven, MA 02568

      Last Sold Summary

      • $762/SF
      • 279 Days On Market
      • Last Sold Price $2,860,000
      • Mar 10, 2025

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

  • /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
  • /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
    • /34

      Est $7,493,099

      Not Listed For Sale

      93 Edgartown Bay Rd, Edgartown, MA 02539

      • 4 Beds
      • 4.5 Baths
      • 3,596 Sq Ft
      • Built 1978
      93 Edgartown Bay Rd, Edgartown, MA 02539

      Last Sold Summary

      • 9% Below List Price
      • $2,294/SF
      • 95 Days On Market
      • Last Sold Price $8,250,000
      • Feb 21, 2025

      Last Listing Agent Jarrett Hurwitz Keller Williams Realty

Showing Results 401 - 440, Page 11 of 18

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