19,346

Dukes County, MA Homes

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  • /35

    $1,225,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    52 Oak Knoll Rd, Vineyard Haven, MA 02568

    Year-round living in the desirable Island Farms Road neighborhood of West Tisbury. This well-built three-bedroom, two-bath home offers a comfortable layout with a first-floor primary bedroom. While ready for your personal updates, it provides a solid foundation to create your forever home. The open kitchen and living area offer a welcoming space for everyday living while the screened porch

    Tina Miller Donnelly + Co.

    52 Oak Knoll Rd, Vineyard Haven, MA 02568
  • /21

    $8,000 Per Month

    • 1 Bed
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    10 James Pond Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

    Karen Overtoom Karen M. Overtoom R.E.

    10 James Pond Way, West Tisbury, MA 02575
  • /44

    $1,890,000

    Sold Aug 29, 2025

    1 Thames Ct, Edgartown, MA 02539

    • 4 Beds
    • 3 Baths
    • 3,270 Sq Ft
    • Built 1981

    Last Sold Summary

    • $578/SF
    • 38 Days On Market

    Current Estimated Value $2,098,088

    Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

    1 Thames Ct, Edgartown, MA 02539
    • /2

      Est $2,519,717

      Not Listed For Sale

      10 Gerts Way, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 2,404 Sq Ft
      • Built 1987
      10 Gerts Way, Edgartown, MA 02539

  • /39

    $3,295,000

    • 5 Beds
    • 4 Baths
    • 2,330 Sq Ft

    29 and 33 Lagoon Pond Rd, Tisbury, MA 02568

    Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking.

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    29 and 33 Lagoon Pond Rd, Tisbury, MA 02568
  • /20

    $12,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,068 Sq Ft
    • House for Rent

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575

    Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

    Karen Overtoom Karen M. Overtoom R.E.

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575
  • /23

    $1,067,000

    Sold Sep 26, 2025

    112 W Spring St, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 1,503 Sq Ft
    • Built 2000

    Last Sold Summary

    • 7% Below List Price
    • $710/SF
    • 9 Days On Market

    Current Estimated Value $1,181,877

    Last Listing Agent Katherine Donahue Sandpiper Realty

    112 W Spring St, Vineyard Haven, MA 02568
    • /39

      Est $3,388,619

      Not Listed For Sale

      18 S Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 4,239 Sq Ft
      • Built 1999
      18 S Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 341 Days On Market

      Last Listing Agent Rose Ryley Wallace & Co. Sotheby's

  • /38

    $1,325,000

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,714 Sq Ft

    116 Franklin Terrace, Vineyard Haven, MA 02568

    Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full

    Pricila Ray Keller Wiliams Realty Cape Cod & Colonial Partners

    116 Franklin Terrace, Vineyard Haven, MA 02568
  • /8

    $16,000 Per Month

    • 7 Beds
    • 3.5 Baths
    • 4,000 Sq Ft
    • House for Rent

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

    Karen Overtoom Karen M. Overtoom R.E.

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
  • /32

    $1,250,000

    Sold Nov 12, 2025

    1054 State Rd, Vineyard Haven, MA 02568

    • 6 Beds
    • 2 Baths
    • 1,845 Sq Ft
    • Built 1881

    Last Sold Summary

    • 16% Below List Price
    • $678/SF
    • 60 Days On Market

    Current Estimated Value $1,365,370

    Last Listing Agent Stephanie Roache Donnelly + Co.

    1054 State Rd, Vineyard Haven, MA 02568
    • /29

      Est $1,929,351

      Not Listed For Sale

      165 W Tisbury Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,750 Sq Ft
      • Built 2007
      165 W Tisbury Rd, Edgartown, MA 02539

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Lisa Gilberto C McManus Realty Group

  • /37

    $3,999,999

    $500K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,715 Sq Ft

    94 Weaver Ln, Vineyard Haven, MA 02568

    Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

    Emma Kennedy Sandpiper Realty, Inc.

    94 Weaver Ln, Vineyard Haven, MA 02568
  • /3

    $13,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    224 N Rd Ch248, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

    Karen Overtoom Karen M. Overtoom R.E.

    224 N Rd Ch248, Chilmark, MA 02535
  • /31

    $3,750,000

    Sold Oct 31, 2025

    29 Oxcart Rd, Aquinnah, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 2009

    Last Sold Summary

    • 11% Below List Price
    • $2,943/SF
    • 380 Days On Market

    Current Estimated Value $3,584,000

    Last Listing Agent Michelle Kelly Tea Lane Associates

    29 Oxcart Rd, Aquinnah, MA 02535
    • /19

      Not Listed For Sale

      43 Look St, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 1,714 Sq Ft
      • Built 1900
      43 Look St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Andrew McElhinney Compass LLC

  • /27

    $869,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled

    Lisa Lucier Anchor Realty of MV

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • /23

    $36,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,556 Sq Ft
    • House for Rent

    74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

    Karen Overtoom Karen M. Overtoom R.E.

    74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
  • /42

    $15,725,000

    Sold Oct 22, 2025

    111 N Water St, Edgartown, MA 02539

    • 6 Beds
    • 4.5 Baths
    • 3,606 Sq Ft
    • Built 1850

    Last Sold Summary

    • 5% Below List Price
    • $4,361/SF
    • 41 Days On Market

    Last Listing Agent Wendy Harman Compass

    111 N Water St, Edgartown, MA 02539
    • /26

      Est $2,043,484

      Not Listed For Sale

      82 South Rd, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,862 Sq Ft
      • Built 1960
      82 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Meg Bodnar Tea Lane Associates

  • /43

    $14,500,000

    $2M PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,705 Sq Ft

    64 Squibnocket Farm Rd, Chilmark, MA 02535

    Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

    Thomas Wallace Wallace & Co. Sotheby's

    64 Squibnocket Farm Rd, Chilmark, MA 02535
  • /17

    $12,000 Per Month

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

    223 Sandpiper Lane Vh405, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

    Karen Overtoom Karen M. Overtoom R.E.

    223 Sandpiper Lane Vh405, Tisbury, MA 02568
  • /29

    $2,450,000

    Sold Jun 02, 2026

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,336 Sq Ft
    • Built 1953

    Last Sold Summary

    • 6% Below List Price
    • $1,834/SF
    • 67 Days On Market

    Last Listing Agent Rene Ben David Ocean Park Realty Inc

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    • /18

      Est $1,805,428

      Not Listed For Sale

      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,461 Sq Ft
      • Built 1994
      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Paul Thoutsis Dockside Real Estate

  • /25

    $3,100,000

    • 1 Bed
    • 1 Bath
    • 1,250 Sq Ft

    114 Meeting House Way Unit 43953, 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 Unit 43953, Edgartown, MA 02539
  • /39

    $110,000 Per Month

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

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • /20

    $929,000

    Sold Aug 18, 2025

    299 Franklin St, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,286 Sq Ft
    • Built 1950

    Last Sold Summary

    • $722/SF
    • 7 Days On Market

    Current Estimated Value $1,032,845

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

    299 Franklin St, Vineyard Haven, MA 02568
    • /10

      Est $991,817

      Not Listed For Sale

      345 Franklin St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,012 Sq Ft
      • Built 1986
      345 Franklin St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Nora Jardin Island Real Estate

  • /66

    $2,675,000

    $275K PRICE DROP
    • 4 Beds
    • 8 Baths
    • 3,740 Sq Ft

    15 21st St N, Edgartown, MA 02539

    Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main

    Jennifer O'hanlon Compass LLC

    15 21st St N, Edgartown, MA 02539
  • /28

    $29,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,871 Sq Ft
    • House for Rent

    76 Mattakesett Way Ed313, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

    Karen Overtoom Karen M. Overtoom R.E.

    76 Mattakesett Way Ed313, Edgartown, MA 02539
  • /42

    $4,150,000

    Sold Feb 19, 2026

    97 Longview Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 5.5 Baths
    • 4,003 Sq Ft
    • Built 2008

    Last Sold Summary

    • 12% Below List Price
    • $1,037/SF
    • 74 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    97 Longview Rd, Vineyard Haven, MA 02568
    • /38

      Est $2,017,870

      Not Listed For Sale

      83 Dolan Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 3,841 Sq Ft
      • Built 1994
      83 Dolan Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Courtney Marek Sandpiper Realty

  • /29

    $49,000,000

    Pending
    • 12 Beds
    • 14 Baths
    • 8,994 Sq Ft

    15 Forever Wild Way, Edgartown, MA 02539

    Great Point is an unprecedented coastal estate encompassing a total of ~32 acres and 5 individual parcels within the coveted 200-acre Herring Creek Farm, just minutes from Edgartown Village and Harbor. This extraordinary property offers location, scale, privacy, and natural beauty, with architecturally significant residences and the rare opportunity to create three additional homes. More than

    Maggie Gold Seelig MGS Group Real Estate LTD

    15 Forever Wild Way, Edgartown, MA 02539
  • /20

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    ** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • /3

    $665,000

    Sold Mar 06, 2026

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557

    • Land
    • 11,133 Sq Ft
    • $2,601,721 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 37 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557
    • /2

      Est $2,840,676

      Not Listed For Sale

      89 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,728 Sq Ft
      • Built 1830
      89 Main St, Vineyard Haven, MA 02568

  • /42

    $7,600,000

    • 5 Beds
    • 4.5 Baths
    • 4,254 Sq Ft

    10 Norton St, Edgartown, MA 02539

    This classically designed Colonial home blends timeless architectural character with fresh, beautifully curated interiors. The first floor welcomes you with a large, sun-filled living room with fireplace, an inviting front parlor, a spacious kitchen with pantry, a screened porch and mudroom/laundry area. Upstairs, the second floor offers four bedrooms and three full baths. The finished lower

    Gerrett Conover Landvest MV

    10 Norton St, Edgartown, MA 02539
  • /8

    $19,000 Per Month

    • 5 Beds
    • 5 Baths
    • 3,137 Sq Ft
    • House for Rent

    19 Morse St, Edgartown, MA 02539

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

    Karen Overtoom Karen M. Overtoom R.E.

    19 Morse St, Edgartown, MA 02539
  • /2

    $880,000

    Sold Oct 17, 2025

    5 Johns Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1987

    Last Sold Summary

    • $645/SF
    • 0 Days On Market

    Current Estimated Value $1,066,290

    Last Listing Agent LINK Email Cache LINK

    5 Johns Way, Oak Bluffs, MA 02557
    • /31

      Est $1,476,638

      Not Listed For Sale

      48 Puritan Dr, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,999 Sq Ft
      • Built 1985
      48 Puritan Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Jennifer B. DaSilva Compass

Showing Results 201 - 240, Page 6 of 18

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