19,346

Dukes County, MA Homes

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  • /26

    $1,395,000

    • 3 Beds
    • 1 Bath
    • 1,066 Sq Ft

    17 Chapman Ln, Edgartown, MA 02539

    OPPORTUNITY KNOCKS: Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat,

    Agent Photo

    Wendy Harman

    Compass | Point B

    17 Chapman Ln, Edgartown, MA 02539
  • /31

    $40,000 Per Month

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • /26

    $1,800,000

    Sold Oct 15, 2025

    82 Skiff Ave, Tisbury, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 1,913 Sq Ft
    • Built 2020

    Last Sold Summary

    • 10% Below List Price
    • $941/SF
    • 128 Days On Market

    Current Estimated Value $1,758,122

    Last Listing Agent Lenny Altieri Premier Properties

    82 Skiff Ave, Tisbury, MA 02568
    • /41

      Est $2,581,592

      Not Listed For Sale

      53 Peases Point Way N, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,704 Sq Ft
      • Built 1928
      53 Peases Point Way N, Edgartown, MA 02539

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Jennifer O'hanlon Compass LLC

  • /40

    $3,675,000

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

    28 Beach Rd, Oak Bluffs, MA 02557

    Enjoy Spectacular Views From This Chic Island Retreat. Wake up to panoramic Vineyard Sound views, watch the Steamship ferries cross to Woods Hole, and enjoy sunsets stretching down the Lagoon. This turnkey 4-bedroom, 2.5-bath home is designed to embrace its remarkable waterfront setting, with covered decks on both sides capturing ocean breezes and water views from nearly every room. The first

    Agent Photo

    Wendy Harman

    Compass

    28 Beach Rd, Oak Bluffs, MA 02557
  • /26

    $50,700 Per Month

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft
    • House for Rent

    6 Trails End Ch241, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

    Karen Overtoom Karen M. Overtoom R.E.

    6 Trails End Ch241, Chilmark, MA 02535
  • /24

    $2,700,000

    Sold Dec 19, 2025

    43 Cottage St, Edgartown, MA 02539

    • 2 Beds
    • 2 Baths
    • 1,112 Sq Ft
    • Built 1945

    Last Sold Summary

    • 16% Below List Price
    • $2,428/SF
    • 7 Days On Market

    Current Estimated Value $3,069,345

    Last Listing Agent Michele Casavant Vineyard Village Realty

    43 Cottage St, Edgartown, MA 02539
    • /38

      Not Listed For Sale

      56 Pinehurst Rd, Edgartown, MA 02539

      • 4 Beds
      • 2.5 Baths
      • 2,328 Sq Ft
      • Built 1973
      56 Pinehurst Rd, Edgartown, MA 02539

      Last Sold Summary

      • 141 Days On Market

      Last Listing Agent Wendy Harman Compass

  • /41

    $1,450,000

    $45K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    44 Prices Way, Edgartown, MA 02539

    Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient

    Agent Photo

    Wendy Harman

    Compass

    44 Prices Way, Edgartown, MA 02539
  • /15

    $5,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    6 Briar Path, Aquinnah, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious

    Karen Overtoom Karen M. Overtoom R.E.

    6 Briar Path, Aquinnah, MA 02535
  • /26

    $1,875,000

    Sold Dec 08, 2025

    14 Rebekahs Way, Vineyard Haven, MA 02568

    • 5 Beds
    • 3 Baths
    • 1,916 Sq Ft
    • Built 1998

    Last Sold Summary

    • 4% Below List Price
    • $979/SF
    • 21 Days On Market

    Current Estimated Value $1,963,707

    Last Listing Agent Sheila Morse Island Real Estate

    14 Rebekahs Way, Vineyard Haven, MA 02568
    • /79

      Not Listed For Sale

      260 South Rd, Chilmark, MA 02535

      • 6 Beds
      • 2.5 Baths
      • 2,604 Sq Ft
      • Built 1688
      260 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /42

    $3,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,056 Sq Ft

    9 Thaxter Ln, Edgartown, MA 02539

    A contemporary Katama retreat, newly refreshed and ready for summer. Set in one of Edgartown’s most coveted coastal enclaves, moments from South Beach, this tri-level home offers sun-filled interiors, generous gathering spaces, strong rental appeal, and a private backyard oasis with an 18x40-foot saltwater pool. The dramatic open-concept living level features vaulted ceilings, a wood-burning

    Agent Photo

    Wendy Harman

    Compass

    9 Thaxter Ln, Edgartown, MA 02539
  • /19

    $17,600 Per Month

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • House for Rent

    50 Carls Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

    Karen Overtoom Karen M. Overtoom R.E.

    50 Carls Way, West Tisbury, MA 02575
  • /19

    $750,000

    Sold Nov 07, 2025

    41 Trinity Park, Oak Bluffs, MA 02557

    • 4 Beds
    • 1 Bath
    • 1,154 Sq Ft
    • Built 1867

    Last Sold Summary

    • 6% Below List Price
    • $650/SF
    • 14 Days On Market

    Current Estimated Value $827,958

    Last Listing Agent Stacy Ickes Donnelly + Co.

    41 Trinity Park, Oak Bluffs, MA 02557
    • /50

      Est $3,211,756

      Not Listed For Sale

      34 S Pond Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 3,311 Sq Ft
      • Built 2000
      34 S Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /38

    $5,795,000

    • 3 Beds
    • 3.5 Baths
    • 3,116 Sq Ft

    7 Katama Dr, Edgartown, MA 02539

    Stylish South Beach Retreat With Resort-Style Pool - Ideally located in the heart of Katama near South Beach, this stylish contemporary home offers the perfect blend of beach living and luxury amenities. Vaulted ceilings, a sleek linear fireplace, and a wall of 12-foot glass doors open the main living area to an expansive mahogany deck, creating seamless indoor-outdoor living. The gourmet

    Agent Photo

    Wendy Harman

    Compass

    7 Katama Dr, Edgartown, MA 02539
  • /9

    $19,000 Per Month

    • 6 Beds
    • 2.5 Baths
    • 2,155 Sq Ft
    • House for Rent

    17 Umbagog Ave Wt109, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Umbagog Ave Wt109, West Tisbury, MA 02575
  • /12

    $37,500,000

    Sold Oct 30, 2025

    48 Witchwood Ln, Edgartown, MA 02539

    • 9 Beds
    • 9.5 Baths
    • 16,209 Sq Ft
    • Built 2000

    Last Sold Summary

    • $2,314/SF
    • 0 Days On Market

    Last Listing Agent Gerrett Conover Landvest MV

    48 Witchwood Ln, Edgartown, MA 02539
    • /14

      Est $6,114,576

      Not Listed For Sale

      100 Meetinghouse Way, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 3,193 Sq Ft
      • Built 1976
      100 Meetinghouse Way, Edgartown, MA 02539

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jennifer B. DaSilva Compass

  • /18

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one

    Lisa Lucier Anchor Realty of MV

    47 Winemack St, Oak Bluffs, MA 02557
  • /32

    $42,000 Per Month

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • /9

    $1,000,000

    Sold Jan 13, 2026

    48 Edgartown - West 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

    Last Listing Agent Mavis Francis eXp Realty LLC

    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    • /37

      Est $2,082,905

      Not Listed For Sale

      41 Smith Hollow Dr, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,391 Sq Ft
      • Built 2001
      41 Smith Hollow Dr, Edgartown, MA 02539

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /35

    $2,500,000

    • 4 Beds
    • 2.5 Baths
    • 1,786 Sq Ft

    9 Codman Spring Rd, Edgartown, MA 02539

    Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Connected to town sewer,

    Madelyn Silvia Wallace & Co. Sotheby's

    9 Codman Spring Rd, Edgartown, MA 02539
  • /2

    $10,000 Per Month

    • 6 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    15 Crowell Lane Wt119, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

    Karen Overtoom Karen M. Overtoom R.E.

    15 Crowell Lane Wt119, West Tisbury, MA 02575
  • /26

    $1,600,000

    Sold Nov 07, 2025

    96 Pondview Dr, Oak Bluffs, MA 02536

    • 4 Beds
    • 2.5 Baths
    • 2,115 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $757/SF
    • 35 Days On Market

    Last Listing Agent Doug Burke Signal House Group at Compass

    96 Pondview Dr, Oak Bluffs, MA 02536
    • /2

      Est $1,389,002

      Not Listed For Sale

      45 Pine Tree Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,400 Sq Ft
      • Built 1961
      45 Pine Tree Ln, Vineyard Haven, MA 02568

  • /5

    $585,000

    $615K PRICE DROP Under Contract
    • Land
    • 39,204 Sq Ft
    • $650,000 per Acre

    87 Whalers Walk Unit 113, Edgartown, MA 02539

    Beautiful .9 acre lot in a tranquil residential neighborhood, ideally located near Morning Glory Farm, Vineyard Golf Club, the bike paths to Edgartown Village, South Beach, and up-island. A unique chance to build your Martha’s Vineyard home in a private yet convenient Edgartown location. This property is subject to M.G.L. Chapter 40A Section 6 of the Affordable Homes Act: a single-family

    Dawn Bellante-Holand Sandpiper Realty

    87 Whalers Walk Unit 113, Edgartown, MA 02539
  • /34

    $25,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,334 Sq Ft
    • House for Rent

    100 Connie's Way Vh401, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. 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 Vh401, Tisbury, MA 02568
  • /6

    $1,200,000

    Sold Aug 14, 2026

    66 Munroe Avenue and 17 Madison Ave Unit 180 &182, Oak Bluffs, MA 02557

    • Land
    • 22,498 Sq Ft
    • $2,323,330 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    66 Munroe Avenue and 17 Madison Ave Unit 180 &182, Oak Bluffs, MA 02557
    • /36

      Est $2,379,823

      Not Listed For Sale

      377 State Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,436 Sq Ft
      • Built 1970
      377 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 518 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /43

    $6,950,000

    • 7 Beds
    • 4.5 Baths
    • 6,921 Sq Ft

    19 Locust Ln, Aquinnah, MA 02535

    There is a town at the end of Martha's Vineyard. The road narrows, the houses thin, and the light changes. This is Aquinnah — the westernmost town, clay cliffs, a lighthouse, and one of the smallest year-round populations on the Vineyard. Compound-scale offerings rarely come to market here.19 Locust Lane is one of them.Nearly 17 acres high above Vineyard Sound, with open water views to

    Creatini Group eXp Realty

    19 Locust Ln, Aquinnah, MA 02535
  • /30

    $20,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • House for Rent

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

    Karen Overtoom Karen M. Overtoom R.E.

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557
  • /42

    $3,695,000

    Sold Nov 20, 2025

    37 Road To the Plains, Edgartown, MA 02539

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1986

    Last Sold Summary

    • $1,478/SF
    • 40 Days On Market

    Current Estimated Value $3,200,983

    Last Listing Agent Wendy Harman Compass

    37 Road To the Plains, Edgartown, MA 02539
    • /32

      Est $3,807,288

      Not Listed For Sale

      94 Marthas Rd, Edgartown, MA 02539

      • 6 Beds
      • 4.5 Baths
      • 3,902 Sq Ft
      • Built 2008
      94 Marthas Rd, Edgartown, MA 02539

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /6

    $975,000

    • Land
    • 1.07 Acres
    • $911,215 per Acre

    68 Pond View Dr, Oak Bluffs, MA 02557

    Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development. Subject to the Town of Oak

    Casandra Hyland Sandpiper Realty, Inc.

    68 Pond View Dr, Oak Bluffs, MA 02557
  • /29

    $11,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    29 Mercier Way, Edgartown, MA 02539

    **SUMMER RATE$ 9,500-$11,000 WEEKLY** Freshly remodeled 4 bed, 2 full bath coastal cape with all new furnishings, flawless finishes, large private yard, close to South Beach, bike path and downtown Edgartown. Large family room with vaulted ceiling and large TV , gorgeous kitchen with all new stainless appliances, vaulted ceilings, sky lights, custom blue stone countertop, island eatery, and wine

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    29 Mercier Way, Edgartown, MA 02539
  • /27

    $1,625,000

    Sold May 12, 2026

    7 Upper Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $497/SF
    • 74 Days On Market

    Current Estimated Value $1,766,366

    Last Listing Agent Lesley Heidt Sandpiper Realty, Inc.

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    • /49

      Not Listed For Sale

      25 Beetle Swamp Rd, Edgartown, MA 02539

      • 6 Beds
      • 4 Baths
      • 3,665 Sq Ft
      • Built 1978
      25 Beetle Swamp Rd, Edgartown, MA 02539

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Gerrett Conover Landvest MV

Showing Results 81 - 120, Page 3 of 18

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