19,907

Dukes County, MA Homes

Section Image
  • /4

    $625,000

    • Land
    • 14,997 Sq Ft
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • /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 $2,959,149

    Last Listing Agent Wendy Harman Compass

    37 Road To the Plains, Edgartown, MA 02539
    • /5

      Est $2,415,474

      Not Listed For Sale

      21 Old Oklahoma Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,657 Sq Ft
      • Built 1948
      21 Old Oklahoma Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /42

    $2,325,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,630 Sq Ft

    81 Whalers Walk, Edgartown, MA 02539

    Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom

    Dawn Bellante Sandpiper Realty, Inc.

    81 Whalers Walk, Edgartown, MA 02539
  • /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 $1,801,024

    Last Listing Agent Lesley Heidt Sandpiper Realty, Inc.

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    • /2

      Est $1,553,686

      Not Listed For Sale

      39 Prices Way, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,532 Sq Ft
      • Built 1986
      39 Prices Way, Edgartown, MA 02539

  • /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
  • /12

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • House for Rent

    43 Edgartown Rd, Vineyard Haven, MA 02568

    Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available

    Karen Overtoom Karen M. Overtoom R.E.

    43 Edgartown Rd, Vineyard Haven, MA 02568
  • /21

    $982,000

    Sold Dec 19, 2025

    25 Windy Hill Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Below List Price
    • $1,002/SF
    • 10 Days On Market

    Current Estimated Value $1,027,886

    Last Listing Agent Rene Jackson Island Real Estate

    25 Windy Hill Rd, Oak Bluffs, MA 02557
    • /14

      Est $2,579,689

      Not Listed For Sale

      30 Pond Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,926 Sq Ft
      • Built 2004
      30 Pond Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 5 Days On Market

  • /15

    $2,490,000

    Pending
    • Land
    • 7.2 Acres
    • $345,833 per Acre

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

    Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

    Robert Kenney Tea Lane Associates

    3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
  • /25

    $13,600 Per Month

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • House for Rent

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

    Karen Overtoom Karen M. Overtoom R.E.

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
  • /31

    $1,350,000

    Sold Aug 15, 2025

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $724/SF
    • 9 Days On Market

    Last Listing Agent Lesley Heidt Sandpiper Realty

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    • /47

      Est $1,773,263

      Not Listed For Sale

      179 Main St, Vineyard Haven, MA 02568

      • 5 Beds
      • 2.5 Baths
      • 2,134 Sq Ft
      • Built 1840
      179 Main St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

  • /36

    $4,500,000

    • 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
  • /8

    $18,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,714 Sq Ft
    • House for Rent

    4 Windy Way Wt143, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

    Karen Overtoom Karen M. Overtoom R.E.

    4 Windy Way Wt143, West Tisbury, MA 02575
  • /19

    $1,865,000

    Sold Dec 04, 2025

    71 Netock Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft
    • Built 1982

    Last Sold Summary

    • 7% Below List Price
    • $661/SF
    • 11 Days On Market

    Current Estimated Value $1,941,086

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
    • /23

      Est $2,047,324

      Not Listed For Sale

      31 Pulpit Ln, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,704 Sq Ft
      • Built 2001
      31 Pulpit Ln, Edgartown, MA 02539

      Last Sold Summary

      • 169 Days On Market

  • /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
  • /8

    $8,250 Per Month

    • 7 Beds
    • 5 Baths
    • 3,528 Sq Ft
    • House for Rent

    227 S Gate Rd Wt120, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • /25

    $1,125,000

    Sold Oct 28, 2025

    140 Longview Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,432 Sq Ft
    • Built 1964

    Last Sold Summary

    • 13% Below List Price
    • $786/SF
    • 97 Days On Market

    Current Estimated Value $1,145,406

    Last Listing Agent Candy DaRosa Feiner Real Estate

    140 Longview Rd, Vineyard Haven, MA 02568
    • /49

      Not Listed For Sale

      670 State Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 2,092 Sq Ft
      • Built 1920
      670 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 68 Days On Market

  • /66

    $2,950,000

    • 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
  • /8

    $17,500 Per Month

    • 8 Beds
    • 4.5 Baths
    • 3,876 Sq Ft
    • House for Rent

    550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing

    Karen Overtoom Karen M. Overtoom R.E.

    550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
  • /28

    $2,075,000

    Sold Sep 29, 2025

    24 Dark Woods Rd, Edgartown, MA 02539

    • 3 Beds
    • 3.5 Baths
    • 2,638 Sq Ft
    • Built 1998

    Last Sold Summary

    • 23% Below List Price
    • $787/SF
    • 372 Days On Market

    Current Estimated Value $2,279,189

    Last Listing Agent Stephanie Burke Portfolio Properties

    24 Dark Woods Rd, Edgartown, MA 02539
    • /35

      Est $1,200,512

      Not Listed For Sale

      29 Dunham Ave, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1965
      29 Dunham Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /28

    $49,000,000

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

    15 Forever Wild Way, Edgartown, MA 02539

    Great Point is a remarkable 32-acre coastal estate within the coveted 200-acre Herring Creek Farm, just minutes from Edgartown Village and Harbor. Offering an extraordinary combination of location, scale, privacy, and natural beauty, the property includes architecturally significant residences and the rare opportunity to create up to three additional homes and complementary structures. More than

    Maggie Gold Seelig MGS Group Real Estate LTD

    15 Forever Wild Way, Edgartown, MA 02539
  • /29

    $18,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,027 Sq Ft
    • House for Rent

    12 Cottle Lane Ed341, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

    Karen Overtoom Karen M. Overtoom R.E.

    12 Cottle Lane Ed341, Edgartown, MA 02539
  • /37

    $1,175,000

    Sold Apr 22, 2026

    112 3rd St N, Edgartown, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $982/SF
    • 139 Days On Market

    Last Listing Agent Kristin Buck Donnelly + Co.

    112 3rd St N, Edgartown, MA 02568
    • /3

      Est $1,455,359

      Not Listed For Sale

      5 Vincent Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1960
      5 Vincent Rd, Vineyard Haven, MA 02568

      Last Sold Summary

  • /19

    $9,250,000

    $1M 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
  • /35

    $22,000 Per Month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • /37

    $7,289,000

    Sold Oct 15, 2025

    25 Osprey Ln, Chilmark, MA 02535

    • 4 Beds
    • 5 Baths
    • 3,777 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $1,930/SF
    • 77 Days On Market

    Last Listing Agent Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • /13

      Est $805,134

      Not Listed For Sale

      32 Clark Ave, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1968
      32 Clark Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market

  • /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
  • /17

    $17,600 Per Month

    • 4 Beds
    • 4 Baths
    • 2,676 Sq Ft
    • House for Rent

    40 Summer Cir, 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. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

    Karen Overtoom Karen M. Overtoom R.E.

    40 Summer Cir, West Tisbury, MA 02575
  • /22

    $435,000

    Sold Aug 26, 2025

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

    • Land
    • 4,356 Sq Ft
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 18 Days On Market

    Last Listing Agent Emma Bryant Studio Realty

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    • /18

      Est $661,953

      Not Listed For Sale

      5 Village Ct Unit 3, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 658 Sq Ft
      • Built 1972
      5 Village Ct Unit 3, Vineyard Haven, MA 02568

      Last Sold Summary

      • 87 Days On Market

Showing Results 121 - 160, Page 4 of 18

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