19,907

Dukes County, MA Homes

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  • /30

    $6,995,000

    • 4 Beds
    • 3 Baths
    • 2,624 Sq Ft

    103 Edgartown Bay Rd, Edgartown, MA 02539

    Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an

    Bonnie Pierce Wallace & Co. Sotheby's

    103 Edgartown Bay Rd, Edgartown, MA 02539
  • /36

    $56,800 Per Month

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

    2 Nonamessett Rd, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

    Karen Overtoom Karen M. Overtoom R.E.

    2 Nonamessett Rd, Edgartown, MA 02539
  • /27

    $1,775,000

    Sold Sep 10, 2025

    13 Hotchkiss Ln, Edgartown, MA 02539

    • 3 Beds
    • 2.5 Baths
    • 2,328 Sq Ft
    • Built 2001

    Last Sold Summary

    • 9% Below List Price
    • $762/SF
    • 61 Days On Market

    Current Estimated Value $1,877,179

    Last Listing Agent Joan Dunayer Martha's Vineyard R.E.

    13 Hotchkiss Ln, Edgartown, MA 02539
    • /28

      Est $2,776,176

      Not Listed For Sale

      5 Katama Dr, Edgartown, MA 02539

      • 3 Beds
      • 3.5 Baths
      • 2,527 Sq Ft
      • Built 1990
      5 Katama Dr, Edgartown, MA 02539

      Last Sold Summary

      • 98 Days On Market

  • /20

    $640,000

    • 1 Bed
    • 1 Bath
    • 354 Sq Ft

    2 Lincoln Ave, Oak Bluffs, MA 02568

    Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

    Stacy Ickes Donnelly + Co.

    2 Lincoln Ave, Oak Bluffs, MA 02568
  • /22

    $20,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • House for Rent

    709 Old County Rd Wt134, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

    Karen Overtoom Karen M. Overtoom R.E.

    709 Old County Rd Wt134, West Tisbury, MA 02575
  • /5

    $1,200,000

    Sold Jan 22, 2026

    58 Marthas Rd Unit 70, Edgartown, MA 02539

    • Land
    • 21,780 Sq Ft
    • $2,400,000 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 179 Days On Market

    Last Listing Agent Katherine Donahue Sandpiper Realty

    58 Marthas Rd Unit 70, Edgartown, MA 02539
    • /34

      Est $4,696,976

      Not Listed For Sale

      25 Down Harbor Rd, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,728 Sq Ft
      • Built 1972
      25 Down Harbor Rd, Edgartown, MA 02539

      Last Sold Summary

      • 107 Days On Market

  • /52

    $2,195,000

    • 5 Beds
    • 3.5 Baths
    • 2,628 Sq Ft

    7 Pip'N Rd, Edgartown, MA 02539

    A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between.Gather around the custom firepit under a canopy of stars, soak in the sauna and

    Dawn Bellante-Holand Sandpiper Realty

    7 Pip'N Rd, Edgartown, MA 02539
  • /21

    $14,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,505 Sq Ft
    • House for Rent

    175 Meetinghouse Way Ed321, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the

    Karen Overtoom Karen M. Overtoom R.E.

    175 Meetinghouse Way Ed321, Edgartown, MA 02539
  • /2

    $1,000,000

    Sold Oct 21, 2025

    32 Pine St, Edgartown, MA 02539

    • 3 Beds
    • 1 Bath
    • 979 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,021/SF
    • 0 Days On Market

    Current Estimated Value $1,165,388

    Last Listing Agent LINK Email Cache LINK

    32 Pine St, Edgartown, MA 02539
    • /42

      Est $3,372,705

      Not Listed For Sale

      16 Mill St, Edgartown, MA 02539

      • 4 Beds
      • 4 Baths
      • 2,090 Sq Ft
      • Built 1908
      16 Mill St, Edgartown, MA 02539

      Last Sold Summary

      • 120 Days On Market

  • /13

    $6,750,000

    • Land
    • 2.11 Acres
    • $3,199,052 per Acre

    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

    Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

    Deb Levin Studio Realty

    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
  • /32

    $100,000 Per Month

    • 5 Beds
    • 4 Baths
    • 4,500 Sq Ft
    • House for Rent

    60 Witchwood Lane Ed317, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $25,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main and upper level have beautiful master suites and also washers & dryers. Easy

    Karen Overtoom Karen M. Overtoom R.E.

    60 Witchwood Lane Ed317, Edgartown, MA 02539
  • /69

    $1,160,000

    Sold Jan 05, 2026

    208 Irenes Way, Tisbury, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,961 Sq Ft
    • Built 2005

    Last Sold Summary

    • 24% Below List Price
    • $392/SF
    • 168 Days On Market

    Current Estimated Value $1,271,403

    Last Listing Agent Emma Bryant Studio Realty

    208 Irenes Way, Tisbury, MA 02568
    • /24

      Est $1,281,685

      Not Listed For Sale

      19 Renear St, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,736 Sq Ft
      • Built 1985
      19 Renear St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 121 Days On Market

  • /69

    $4,175,000

    • 6 Beds
    • 3.5 Baths
    • 3,397 Sq Ft

    19 Kitts Field Cir, Edgartown, MA 02539

    Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence with three levels of living space, a charming two-bedroom guest house, pool house, pool, spa,

    Michele Casavant Vineyard Village Realty

    19 Kitts Field Cir, Edgartown, MA 02539
  • /8

    $3,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • House for Rent

    849 State Rd Unit 1, Aquinnah, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

    Karen Overtoom Karen M. Overtoom R.E.

    849 State Rd Unit 1, Aquinnah, MA 02535
  • /8

    $435,000

    Sold Apr 16, 2026

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539

    • Land
    • 22,651 Sq Ft
    • $836,538 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 131 Days On Market

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539
    • /29

      Est $2,203,041

      Not Listed For Sale

      22 Kitts Field Cir, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,552 Sq Ft
      • Built 1986
      22 Kitts Field Cir, Edgartown, MA 02539

      Last Sold Summary

      • 11 Days On Market

  • /4

    $639,000

    • Land
    • 12,998 Sq Ft
    • $2,141,421 per Acre

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process. Conveniently located just off

    Tina Miller Donnelly + Co

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
  • /8

    $11,800 Per Month

    • 4 Beds
    • 4 Baths
    • 2,612 Sq Ft
    • House for Rent

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

    Karen Overtoom Karen M. Overtoom R.E.

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
  • /7

    $375,000

    Sold Apr 06, 2026

    99 Cygnet Way Unit 103, Chilmark, MA 02535

    • Land
    • 8,712 Sq Ft
    • $1,875,000 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 120 Days On Market

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    99 Cygnet Way Unit 103, Chilmark, MA 02535
    • /40

      Est $2,241,965

      Not Listed For Sale

      1 Old Squaw Cir, Edgartown, MA 02539

      • 4 Beds
      • 2.5 Baths
      • 2,008 Sq Ft
      • Built 1996
      1 Old Squaw Cir, Edgartown, MA 02539

      Last Sold Summary

      • 52 Days On Market

  • /3

    $2,850,000

    • Land
    • 1.52 Acres
    • $1,875,000 per Acre

    39 Slough Cove Rd Unit 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

    Francine Agnoli The Agency Martha's Vineyard

    39 Slough Cove Rd Unit part of, Edgartown, MA 02539
  • /26

    $7,000 Per Month

    • 7 Beds
    • 1.5 Baths
    • 2,900 Sq Ft
    • House for Rent

    39 N Neck Rd, Edgartown, MA 02539

    Historic Quaint Waterfront Cottage with spectacular 180 degree views of Edgartown Harbor, Oak Bluffs, Cape Cod and Cape Poge, Over 200 feet of secluded, completely private beach, The back yard abuts the fairways and club house of the ''Royal Ancient Chappaquiddick Links'' Private Golf Course. (You must pay dues to play golf), Great outdoor shower. You can see the fireworks (in 5 locations at

    Charles Petitti Coldwell Banker Realty - Newton

    39 N Neck Rd, Edgartown, MA 02539
  • /20

    $1,150,000

    Sold Jun 13, 2025

    46 Old Coach Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,374 Sq Ft
    • Built 1981

    Last Sold Summary

    • 10% Below List Price
    • $837/SF
    • 43 Days On Market

    Current Estimated Value $1,253,621

    Last Listing Agent Lisa Gilberto C McManus Realty Group

    46 Old Coach Rd, Vineyard Haven, MA 02568
    • /47

      Est $4,938,852

      Not Listed For Sale

      5 Armstrong Ln, Edgartown, MA 02539

      • 3 Beds
      • 3.5 Baths
      • 4,084 Sq Ft
      • Built 2005
      5 Armstrong Ln, Edgartown, MA 02539

      Last Sold Summary

      • 572 Days On Market

  • /30

    $8,950,000

    • 5 Beds
    • 7 Baths
    • 4,078 Sq Ft

    1 Field Club Dr, Edgartown, MA 02539

    Nestled within the prestigious Field Club, this exceptional five-bedroom compound captures the essence of refined island living, blending timeless elegance with modern sophistication. A welcoming foyer introduces a light-filled, open-concept main level designed for both comfort and entertaining. The gourmet kitchen is a standout, featuring high-end appliances, granite countertops, and custom

    Tom Wallace

    1 Field Club Dr, Edgartown, MA 02539
  • /8

    $4,800 Per Month

    • 3 Beds
    • 3 Baths
    • 3,279 Sq Ft
    • House for Rent

    165 Christiantown Rd, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

    Karen Overtoom Karen M. Overtoom R.E.

    165 Christiantown Rd, West Tisbury, MA 02575
  • /2

    $15,000,000

    Sold Apr 02, 2026

    38 Cow Bay Rd, Edgartown, MA 02539

    • 6 Beds
    • 8 Baths
    • 5,586 Sq Ft
    • Built 1999

    Last Sold Summary

    • 10% Below List Price
    • $2,685/SF
    • 0 Days On Market

    Last Listing Agent Gerrett Conover Landvest MV

    38 Cow Bay Rd, Edgartown, MA 02539
    • /37

      Est $1,875,943

      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

  • /36

    $3,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,686 Sq Ft

    4 Nomans Watch Rd, Aquinnah, MA 02535

    Perched on 2.7 acres in one of Aquinnah’s most breathtaking settings, this beautifully sited coastal retreat offers sweeping views over the Atlantic and Noman’s Land from its elevated position. Designed to embrace the light and scenery, the main level features an open living/dining/kitchen area wrapped in walls of windows—an airy, sun-soaked space where ocean views take center stage. The

    Jennifer O'hanlon Compass LLC

    4 Nomans Watch Rd, Aquinnah, MA 02535
  • /32

    $36,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • /2

    $900,000

    Sold Sep 17, 2025

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535

    • Land
    • 3.05 Acres
    • $295,082 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 83 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    • /34

      Est $2,340,864

      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

  • /19

    $925,000

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft

    15 Second Ave, Oak Bluffs, MA 02557

    Step into this beautifully updated Vineyard cottage, where modern comfort meets coastal charm. The living room, kitchen, dining area, and first-floor full bath were all thoughtfully renovated in 2023. The living space features freshly updated furnishings, contemporary lighting, and light grey beadboard walls, creating an open and inviting atmosphere that flows seamlessly into the dining and

    Susie Wallo Compass LLC

    15 Second Ave, Oak Bluffs, MA 02557
  • /41

    $14,500 Per Month

    • 5 Beds
    • 5.5 Baths
    • 3,392 Sq Ft
    • House for Rent

    76 School House Lane Wt101, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

    Karen Overtoom Karen M. Overtoom R.E.

    76 School House Lane Wt101, West Tisbury, MA 02575
  • /22

    $4,250,000

    Sold Sep 09, 2025

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568

    • 7 Beds
    • 6 Baths
    • 4,125 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $1,030/SF
    • 21 Days On Market

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

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • /34

      Est $4,044,751

      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

Showing Results 321 - 360, Page 9 of 18

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