19,346

Dukes County, MA Homes

Section Image
  • /39

    $1,575,000

    Pending
    • 3 Beds
    • 3 Baths
    • 1,621 Sq Ft

    27 Laurel Ave, Oak Bluffs, MA 02557

    Located in exclusive East Chop, this sun-filled 3BR Cottage blends authentic Martha’s Vineyard charm with modern coastal living. Immaculate, fully furnished, and turn-key, this property presents a phenomenal island retreat or a lucrative investment with fantastic rental potential.The main home pairs classic character with upgraded 200-amp electric, featuring bright spaces, a large kitchen, and

    Lisa Sheehan Berkshire Hathaway HomeServices Robert Paul Properties

    27 Laurel Ave, Oak Bluffs, MA 02557
  • /23

    $24,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,637 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • /2

    $14,750,000

    Sold Jun 26, 2026

    14 Bayside South-Lot 5 Unit 159.15, Edgartown, MA 02539

    • Land
    • 4.72 Acres
    • $3,125,000 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Gerrett Conover Landvest MV

    14 Bayside South-Lot 5 Unit 159.15, Edgartown, MA 02539
    • /27

      Est $1,623,466

      Not Listed For Sale

      13 Saddle Club Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,729 Sq Ft
      • Built 1988
      13 Saddle Club Rd, Edgartown, MA 02539

      Last Sold Summary

      • 227 Days On Market

      Last Listing Agent Elaine Miller & Partners Realty, EMPR Sandpiper Realty

  • /4

    $809,000

    • Land
    • 16,988 Sq Ft
    • $2,074,359 per Acre

    7 Highland Ave, Oak Bluffs, MA 02557

    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, LLC

    7 Highland Ave, Oak Bluffs, MA 02557
  • /35

    $112,000 Per Month

    • 6 Beds
    • 9 Baths
    • 5,732 Sq Ft
    • House for Rent

    31 Lamberts Cove Road Vh434, Tisbury, MA 02568

    Karen Overtoom Karen M. Overtoom R.E.

    31 Lamberts Cove Road Vh434, Tisbury, MA 02568
  • /45

    $2,100,000

    Sold Nov 25, 2025

    6 Tabor Hills, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,544 Sq Ft
    • Built 1993

    Last Sold Summary

    • 11% Below List Price
    • $825/SF
    • 48 Days On Market

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    6 Tabor Hills, Chilmark, MA 02535
    • /2

      Est $973,648

      Not Listed For Sale

      84 Pine Tree Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,116 Sq Ft
      • Built 1980
      84 Pine Tree Rd, Vineyard Haven, MA 02568

  • /12

    $3,400,000

    New Construction
    • 3 Beds
    • 4.5 Baths
    • 3,260 Sq Ft

    27 Double Ox Rd, Oak Bluffs, MA 02557

    Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living

    Lesley Heidt Sandpiper Realty, Inc.

    27 Double Ox Rd, Oak Bluffs, MA 02557
  • /18

    $10,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,439 Sq Ft
    • House for Rent

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

    Karen Overtoom Karen M. Overtoom R.E.

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
  • /2

    $1,100,000

    Sold Oct 29, 2025

    11 Quammox Rd, Edgartown, MA 02539

    • 2 Beds
    • 1 Bath
    • 685 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,606/SF
    • 0 Days On Market

    Current Estimated Value $1,170,034

    Last Listing Agent LINK Email Cache LINK

    11 Quammox Rd, Edgartown, MA 02539
    • /2

      Est $1,664,450

      Not Listed For Sale

      55 Pinehurst Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1996
      55 Pinehurst Rd, Edgartown, MA 02539

  • /19

    $7,950,000

    $3M PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    33 Goethals Way, Vineyard Haven, MA 02568

    A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

    Buder Team Sandpiper Realty, Inc.

    33 Goethals Way, Vineyard Haven, MA 02568
  • /10

    $8,500 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

    Karen Overtoom Karen M. Overtoom R.E.

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
  • /30

    $1,050,000

    Sold Oct 06, 2025

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • 11% Below List Price
    • $794/SF
    • 62 Days On Market

    Current Estimated Value $1,066,886

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

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

      Not Listed For Sale

      41 Cobbs Hill Rd, Chilmark, MA 02535

      • 9 Beds
      • 9 Baths
      • 7,846 Sq Ft
      • Built 1993
      41 Cobbs Hill Rd, Chilmark, MA 02535

  • /2

    $6,250,000

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

    68 Turkeyland Cove Rd, Edgartown, MA 02539

    Nestled in one of Edgartown's most sought-after waterfront neighborhoods, Turkeyland Cove offers the best of both worlds: a tranquil, nature-immersed sanctuary that feels miles from anywhere, yet remains moments from everything Martha's Vineyard has to offer. This exclusive enclave strikes a perfect balance between natural beauty, sophisticated living, and convenient access to Island

    Emma Kennedy Sandpiper Realty

    68 Turkeyland Cove Rd, Edgartown, MA 02539
  • /41

    $13,500 Per Month

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

    14 Bernard Cir, Vineyard Haven, MA 02568

    ** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    14 Bernard Cir, Vineyard Haven, MA 02568
  • /36

    $2,900,000

    Sold Mar 30, 2026

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft
    • Built 1988

    Last Sold Summary

    • $561/SF
    • 35 Days On Market

    Current Estimated Value $2,968,781

    Last Listing Agent Casandra Hyland Sandpiper Realty, Inc.

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    • /42

      Not Listed For Sale

      67 Hidden Village Rd, Vineyard Haven, MA 02568

      • 7 Beds
      • 5.5 Baths
      • 4,476 Sq Ft
      • Built 1997
      67 Hidden Village Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 347 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co.

  • /46

    $2,400,000

    • 5 Beds
    • 3.5 Baths
    • 3,873 Sq Ft

    50 Hidden Cove Rd, Edgartown, MA 02539

    Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering

    Sean Federowicz Landmarks at TODAY Real Estate

    50 Hidden Cove Rd, Edgartown, MA 02539
  • /10

    $11,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    15 Price's Way Ed322, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

    Karen Overtoom Karen M. Overtoom R.E.

    15 Price's Way Ed322, Edgartown, MA 02539
  • /36

    $1,275,000

    Sold Jul 31, 2026

    9 Brunswick Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,033 Sq Ft
    • Built 1862

    Last Sold Summary

    • $1,234/SF
    • 1 Day On Market

    Current Estimated Value $1,252,940

    Last Listing Agent Alice Pierce Coldwell Banker Realty - Hingham

    9 Brunswick Ave, Oak Bluffs, MA 02557
    • /16

      Est $1,253,103

      Not Listed For Sale

      31 Music St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,150 Sq Ft
      • Built 1817
      31 Music St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /66

    $1,899,000

    $101K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,075 Sq Ft

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

    Valene Pires The Agency

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • /16

    $5,000 Per Month

    • 1 Bath
    • 400 Sq Ft
    • House for Rent

    90 Edgartown Rd, Vineyard Haven, MA 02568

    *Summer Weekly Rate** Inquire For Long-term Off-Season Rates. Renovated Studio Cottage on Martha's Vineyard w/private feel. Within walking distance to shops, dining, and the ferry. Lots of trees for year-round enjoyment. Open floor plan with Murphy bed for additional space and a large comfortable sofa, galley kitchen with granite countertops, stainless steel appliances, amazing tiled bathroom

    Kim Seawright Generations Realty Group

    90 Edgartown Rd, Vineyard Haven, MA 02568
  • /23

    $1,800,000

    Sold Aug 26, 2025

    12 Martha's Park Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 1.5 Baths
    • 1,351 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $1,332/SF
    • 0 Days On Market

    Current Estimated Value $1,872,478

    Last Listing Agent Michele Moore Island Real Estate

    12 Martha's Park Rd, Oak Bluffs, MA 02557
    • /29

      Not Listed For Sale

      30 Mill Hill Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 2,800 Sq Ft
      • Built 1850
      30 Mill Hill Rd, Edgartown, MA 02539

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Wendy Harman Compass

  • /8

    $1,325,000

    $250K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    47 Quenames Rd, Chilmark, MA 02535

    On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

    Dawn Bellante Sandpiper Realty, Inc.

    47 Quenames Rd, Chilmark, MA 02535
  • /19

    $30,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,600 Sq Ft
    • House for Rent

    37 Sachem Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

    Karen Overtoom Karen M. Overtoom R.E.

    37 Sachem Cir, West Tisbury, MA 02575
  • /12

    $860,000

    Sold Feb 09, 2026

    8 Hitchings Cir, Oak Bluffs, MA 02557

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $698/SF
    • 22 Days On Market

    Last Listing Agent Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
    • /46

      Est $6,600,732

      Not Listed For Sale

      79 Rachels Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,278 Sq Ft
      • Built 1983
      79 Rachels Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Jennifer O'hanlon Compass LLC

  • /33

    $1,225,000

    • 1 Bed
    • 2 Baths
    • 1,428 Sq Ft

    323 County Rd, Oak Bluffs, MA 02557

    This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and

    Nancy Beckwith Anchor Realty of Martha's Vineyard

    323 County Rd, Oak Bluffs, MA 02557
  • /19

    $24,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • /27

    $1,800,000

    Sold Dec 02, 2025

    16 Schoolhouse Rd, Edgartown, MA 02539

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Below List Price
    • $1,029/SF
    • 123 Days On Market

    Current Estimated Value $2,004,389

    Last Listing Agent Lesley Heidt Sandpiper Realty

    16 Schoolhouse Rd, Edgartown, MA 02539
    • /2

      Est $1,522,729

      Not Listed For Sale

      23 Anthiers Way, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 2,066 Sq Ft
      • Built 1950
      23 Anthiers Way, Edgartown, MA 02539

  • /47

    $3,690,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,108 Sq Ft

    13 Plantingfield Way, Edgartown, MA 02539

    Set in the heart of Edgartown Village, this pristine Cape offers an exceptional combination of charm, comfort, and in-town convenience. Just moments from boutique shopping, acclaimed galleries, fine dining, and the scenic harbor, this four-bedroom, three-bath home captures the quintessential Vineyard lifestyle. Two entrances enhance the home’s functionality: a formal front entry leads directly to

    Stephanie Roache Donnelly + Co

    13 Plantingfield Way, Edgartown, MA 02539
  • /39

    $46,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    99 Pond Road Wt104, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

    Karen Overtoom Karen M. Overtoom R.E.

    99 Pond Road Wt104, West Tisbury, MA 02575
  • /31

    $1,685,000

    Sold Oct 09, 2025

    126 Border Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 3 Baths
    • 2,251 Sq Ft
    • Built 1979

    Last Sold Summary

    • 16% Below List Price
    • $749/SF
    • 337 Days On Market

    Current Estimated Value $1,911,919

    Last Listing Agent Natalie Conroy Conroy & Company R.E., Inc.

    126 Border Rd, Vineyard Haven, MA 02568
    • /43

      Not Listed For Sale

      7 N Bog Rd, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,094 Sq Ft
      • Built 1994
      7 N Bog Rd, Edgartown, MA 02539

      Last Sold Summary

      • 276 Days On Market

      Last Listing Agent Robin Perschel Feiner Real Estate

Showing Results 241 - 280, Page 7 of 18

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