19,907

Dukes County, MA Homes

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  • /48

    $3,950,000

    • 3 Beds
    • 4.5 Baths
    • 3,314 Sq Ft

    20 Edson Forrest Rd, West Tisbury, MA 02575

    Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. A full restoration of this this three-bedroom house (with six-bedroom septic) in 2022 created a luxury home with a thoughtful layout, 2 story expansion, and exceptional

    Meg Bodnar Tea Lane Associates

    20 Edson Forrest Rd, West Tisbury, MA 02575
  • /27

    $18,840 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    21 William St Vh430, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

    Karen Overtoom Karen M. Overtoom R.E.

    21 William St Vh430, Tisbury, MA 02568
  • /2

    $1,700,000

    Sold Oct 20, 2025

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    • 5 Beds
    • 3 Baths
    • 1,803 Sq Ft
    • Built 1982

    Last Sold Summary

    • $943/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    • /41

      Est $2,540,413

      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

  • /39

    $1,595,000

    $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,514 Sq Ft

    26 Sea Glen Rd, Oak Bluffs, MA 02557

    Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor

    Jennifer B. DaSilva Compass

    26 Sea Glen Rd, Oak Bluffs, MA 02557
  • /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 $1,689,952

    Last Listing Agent Lenny Altieri Premier Properties

    82 Skiff Ave, Tisbury, MA 02568
    • /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

  • /36

    $5,325,000

    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    4 Canonicus Ave, 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 $2,965,827

    Last Listing Agent Michele Casavant Vineyard Village Realty

    43 Cottage St, Edgartown, MA 02539
    • /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

  • /30

    $1,850,000

    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft

    99 Old Purchase Rd, Edgartown, MA 02539

    Enjoying a private setting at the end of a quiet Edgartown cul-de-sac, this post-and-beam home is set on .71 acres with easy access to more than 25 acres of Land Bank conservation land. Conveniently located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, the property offers both privacy and accessibility. Filled with natural light, the home features a well-designed

    Stephanie Roache Donnelly + Co

    99 Old Purchase Rd, Edgartown, MA 02539
  • /15

    $5,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • House for Rent

    85 Winemack St, Oak Bluffs, MA 02557

    This charming property located in East Chop is the perfect retreat for up to 6 guests, offering 3 cozy bedrooms and 2 full bathrooms. Walk into the spacious living area complete with comfortable seating and a Smart TV for your entertainment needs. The fully equipped kitchen features modern appliances and a kitchen island with seating for the kids. Enjoy your meals at the dining table with seating

    Benjamin Snow Coldwell Banker Realty - Boston

    85 Winemack St, Oak Bluffs, MA 02557
  • /7

    $650,000

    Sold Aug 14, 2025

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

    • Land
    • 8,712 Sq Ft
    • $3,250,000 per Acre

    Last Sold Summary

    • 7 Days On Market

    Last Listing Agent Deb Hancock Hancock Real Estate

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    • /52

      Not Listed For Sale

      2 Squibnocket Rd, Chilmark, MA 02535

      • 6 Beds
      • 5.5 Baths
      • 5,808 Sq Ft
      • Built 2008
      2 Squibnocket Rd, Chilmark, MA 02535

      Last Sold Summary

      • 297 Days On Market

  • /7

    $3,100,000

    • Land
    • 3.04 Acres
    • $1,019,737 per Acre

    114 Meeting House Way, Edgartown, MA 02539

    3 Acre Katama Building Lot with Existing Guest House.This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South

    Rose Ryley Wallace & Co. Sotheby's

    114 Meeting House 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
  • /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 $796,752

    Last Listing Agent Stacy Ickes Donnelly + Co.

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

      Est $2,937,566

      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

  • /35

    $5,200,000

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper

    Bonnie Pierce Wallace & Co. Sotheby's

    49 Gosnold's Way, Chilmark, MA 02535
  • /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
  • /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 $5,878,856

      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

  • /66

    $4,950,000

    • 6 Beds
    • 5.5 Baths
    • 3,998 Sq Ft

    15 Tamarack Ln, Oak Bluffs, MA 02557

    Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane presents a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views of the 7th fairway and 8th tee box, across to Sengekontacket Pond, offering a serene backdrop of lush greens and distant water. The historic

    Stephanie Roache Donnelly + Co

    15 Tamarack Ln, Oak Bluffs, MA 02557
  • /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
  • /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

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

      Est $1,999,231

      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

  • /23

    $3,988,000

    $300K PRICE DROP Pending
    • 7 Beds
    • 3.5 Baths
    • 2,461 Sq Ft

    69 School St, Edgartown, MA 02539

    Located in the heart of Edgartown Village, this circa 1840 Greek Revival residence offers a rare opportunity to own a piece of island history on a coveted block. The property features a total of seven bedrooms across the main house and carriage house, making it a superb destination for family and guests. The main house features wide plank hardwood flooring and bright and sunny spaces with five

    Peyton Wallace Studio Realty

    69 School St, Edgartown, MA 02539
  • /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
  • /31

    $1,325,000

    Sold Jun 30, 2025

    191 Spring Hill Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 4 Baths
    • 2,292 Sq Ft
    • Built 1992

    Last Sold Summary

    • 5% Below List Price
    • $578/SF
    • 10 Days On Market

    Current Estimated Value $1,250,478

    Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

    191 Spring Hill Rd, Vineyard Haven, MA 02568
    • /2

      Est $1,370,061

      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

  • /9

    $1,900,000

    • Land
    • 15.05 Acres
    • $126,246 per Acre

    0 High Mark Rd Unit 66, Chilmark, MA 02535

    A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on the island today.The parcel directly abuts the nearly 80 acres of conservation land at the

    Russell Maloney Russell Maloney Real Estate

    0 High Mark Rd Unit 66, Chilmark, MA 02535
  • /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
    • /36

      Est $2,288,995

      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

  • /53

    $6,750,000

    • 5 Beds
    • 3.5 Baths
    • 4,050 Sq Ft

    78 Hammett Rd, Chilmark, MA 02535

    Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

    Robert Kenney Tea Lane Associates

    78 Hammett Rd, Chilmark, MA 02535
  • /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
  • /34

    $1,050,000

    Sold Jun 30, 2025

    160 Bernard Cir, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,606 Sq Ft
    • Built 1977

    Last Sold Summary

    • 12% Below List Price
    • $654/SF
    • 45 Days On Market

    Current Estimated Value $1,170,069

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    160 Bernard Cir, Vineyard Haven, MA 02568
    • /32

      Est $3,676,661

      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

Showing Results 81 - 120, Page 3 of 18

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