4,271

Dukes, MA Homes

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  • /38

    $4,195,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    This beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • /21

    $7,000 per month

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

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt not to long ago it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room ,dining area and fireplace area. Walk out the

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • /22

    $1,607,000 Sold Jul 10, 2025

    • 2,850 Sq Ft
    • $564/SF
    • 354 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1978

    10 N Abels Hill Rd, Chilmark, MA 02535

    A rare opportunity in the iconic Abel's Hill Association which offers private association beach access, three tennis courts and walking trails. This multi-level Chilmark home was designed and built as an homage to architect Frank Lloyd Wright's ethos of open living spaces with flowing sightlines from room to room. The main house has a pocket view to the Atlantic that opens in the fall and winter

    Elissa Lash Tea Lane Associates

    10 N Abels Hill Rd, Chilmark, MA 02535
    • /40

      Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 4,500 Sq Ft

      1005 State Rd, West Tisbury, MA 02575

      1005 State Rd, West Tisbury, MA 02575
  • /41

    $3,600,000

    • 3 Beds
    • 4 Baths
    • 2,500 Sq Ft

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • /14

    $8,400 per month

    • 4 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • House for Rent

    39 Old Coach Rd, West Tisbury, MA 02568

    Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

    Joseph D'Amico Dee Development Company

    39 Old Coach Rd, West Tisbury, MA 02568
  • /44

    $37,000,000 Sold Jul 10, 2025

    • 7,846 Sq Ft
    • $4716/SF
    • 39 Days On Market
    • 8 Beds
    • 5.5 Baths
    • Built 1993

    41 Cobbs Hill Rd, Chilmark, MA 02535

    One of the most exclusive estates across the Northeast, Blue Heron Farm on Martha's Vineyard is set on nearly 30 acres of lush landscaping along the shores of Tisbury Great Pond. The former summer residence of President Obama and family, chosen for its incredible privacy, serenity and significance, this multi-generational compound is protected by surrounding farmland and mature trees.

    Brian Dougherty Corcoran Property Advisors

    41 Cobbs Hill Rd, Chilmark, MA 02535
    • /30

      Est $2,500,413 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,555 Sq Ft

      10 Crow Hollow Rd, Vineyard Haven, MA 02568

      10 Crow Hollow Rd, Vineyard Haven, MA 02568
  • /36

    $3,250,000

    • 4 Beds
    • 4 Baths
    • 2,515 Sq Ft

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

    Rebecca V Conroy Conroy & Company R.E., Inc.

    300 North Rd, Chilmark, MA 02535
  • /20

    $4,250 per month

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

    11 Hammett Ln, Chilmark, MA 02535

    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 location off North Road

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • /3

    $3,100,000 Sold Jul 03, 2025

    • 1,500 Sq Ft
    • $2067/SF
    • 6 Beds
    • 3 Baths
    • Built 1975

    10 Basin Rd, Chilmark, MA 02535

    Unique compound in the heart of Menemsha - one of a kind!The cottage (520 sq.ft.), the chandlery buikding(5968 sq.ft.) and deli with an apartment(2172 sq.ft.) on just under an acre of land has tremendous potential for the right buyer!Special permits are required from the town to operate a business but they have approved a deli/restuarant, small stores and a commercial kitchen in the past.

    Julianna Flanders Flanders Real Estate

    10 Basin Rd, Chilmark, MA 02535
    • /4

      Est $2,968,039 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,789 Sq Ft

      188 Pond Rd, Vineyard Haven, MA 02568

      188 Pond Rd, Vineyard Haven, MA 02568
  • /39

    $3,299,000

    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    Nestled in one of the island’s most sought-after locations, this exceptional property offers refined coastal living with access to the famed Lambert’s Cove Beach yet a short drive to VH.Thoughtfully designed, it features 3 spacious bedrooms each with an en suite bath, providing comfort and privacy for all. Primary suite is a true retreat with a brand new luxurious bathroom. At the heart of the

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, 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
  • /42

    $2,900,000 Sold Jul 03, 2025

    • 4,476 Sq Ft
    • $648/SF
    • 347 Days On Market
    • 7 Beds
    • 5.5 Baths
    • Built 1997

    67 Hidden Village Rd, Vineyard Haven, MA 02568

    Picturesquely sited on a spacious 4.6-acre parcel this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels providing spacious yet private surroundings. The main living

    Stephanie Roache Donnelly + Co.

    67 Hidden Village Rd, Vineyard Haven, MA 02568
    • /34

      Est $2,551,353 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 1 Sq Ft

      248 Pond Rd, Vineyard Haven, MA 02568

      248 Pond Rd, Vineyard Haven, MA 02568
  • /36

    $5,450,000

    • 5 Beds
    • 4 Baths
    • 2,913 Sq Ft

    122 Old Farm Rd, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
  • /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
  • /36

    $1,950,000 Sold Jul 02, 2025

    • 2,691 Sq Ft
    • $725/SF
    • 30 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1976

    51 Black Brook Crossing Rd, West Tisbury, MA 02568

    This charming 4 bed/2.5 bath Cape style home is set in a perfect setting, carefully sited on 1 acre bordered by a beautiful stone wall with mature plantings. Newly renovated kitchen with plenty of cabinets and storage, quartz counters and dining room with sliders to a screened-in porch. There is a den and living room with access to a spacious deck. The Great Room features cathedral ceilings,

    Brenda Galligan Karen M. Overtoom R.E.

    51 Black Brook Crossing Rd, West Tisbury, MA 02568
    • /25

      Est $2,093,611 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,636 Sq Ft

      131 Shubael Weeks Path, Vineyard Haven, MA 02568

      131 Shubael Weeks Path, Vineyard Haven, MA 02568
  • /42

    $4,600,000

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS- 15 Old Farm Rd, sits on over 3 beautiful acres, blends refined architecture with serene natural beauty. Reimagined in 2020 by Peter Breese and crafted by Doug Best, this timeless retreat offers open-concept living, anchored by a stunning kitchen, large pantry, screen porch, and a stone fireplace, with seamless indoor-outdoor flow. The main level includes a sunny primary suite

    Tina Miller Compass

    15 Old Farm Rd, Chilmark, MA 02535
  • /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
  • /2

    $1,595,000 Sold Jul 01, 2025

    • 1,176 Sq Ft
    • $1356/SF
    • 2 Beds
    • 2 Baths
    • Built 1998

    10 Red Pony Rd, West Tisbury, MA 02568

    Pastoral and perfect. Room to grow or just move in.

    Lisa Da silva Compass | Point B

    10 Red Pony Rd, West Tisbury, MA 02568
    • /79

      Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 2,604 Sq Ft

      260 South Rd, Chilmark, MA 02535

      260 South Rd, Chilmark, MA 02535
  • /34

    $5,450,000

    • 5 Beds
    • 4.5 Baths
    • 2,913 Sq Ft

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • /12

    $6,180 per month

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • House for Rent

    44 Music St Wt153, West Tisbury, MA 02575

    PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

    Karen Overtoom Karen M. Overtoom R.E.

    44 Music St Wt153, West Tisbury, MA 02575
  • /32

    $3,925,000 Sold Jul 01, 2025

    • 5,603 Sq Ft
    • $701/SF
    • 238 Days On Market
    • 6 Beds
    • 7 Baths
    • Built 1995

    140 Merry Farm Rd, Vineyard Haven, MA 02568

    Site of the original Rainbow Farm, this 8.05-acre parcel is one of the most beautiful pieces of land in West Tisbury. The warm and convivial 5,000 sq ft home with its 4 bedrooms looks out onto a setting that is as if from a bygone era, the vast fields stretching into the distance. The spring-fed pond is a centerpiece of the pastoral view. The home itself has many surprising and charming design

    Mark Jenkins Wallace & Co. Sotheby's

    140 Merry Farm Rd, Vineyard Haven, MA 02568
    • /31

      Est $3,145,737 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,300 Sq Ft

      68 Meeting House Rd, Chilmark, MA 02535

      68 Meeting House Rd, Chilmark, MA 02535
  • /30

    $3,900,000

    • 4 Beds
    • 2 Baths
    • 2,813 Sq Ft

    179 Tisbury Ln E, West Tisbury, MA 02575

    Seven Gates Farm: This warm and convivial home in one of the island’s most desirable communities is less than 1/10th of a mile to the private association beach. The house was designed to accentuate indoor-outdoor living; there is generous decking for morning or afternoon sun, and a screened porch which is the perfect place to enjoy shade and breeze after a day spent at one of the nearby beaches.

    Mark Jenkins Wallace & Co. Sotheby's

    179 Tisbury Ln E, West Tisbury, MA 02575
  • /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

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • /6

    $430,000 Sold Jun 30, 2025

    • Land
    • 1.40 Acres
    • $307,143 per Acre
    • 0 Days On Market

    0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535

    Not listed in LINK.

    LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535
    • /36

      Est $2,321,551 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,436 Sq Ft

      377 State Rd, Vineyard Haven, MA 02568

      377 State Rd, Vineyard Haven, MA 02568
  • /25

    $3,600,000

    • 3 Beds
    • 3 Baths
    • 4,382 Sq Ft

    88 & 90 Quenames Rd, Chilmark, MA 02535

    Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

    Julianna Flanders Flanders Real Estate

    88 & 90 Quenames Rd, 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
  • /47

    $1,595,500 Sold Jun 23, 2025

    • 1,822 Sq Ft
    • $876/SF
    • 73 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2003

    21 Coffins Field Rd, Edgartown, MA 02539

    EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well

    Helena Kirschenbaum Studio Realty

    21 Coffins Field Rd, Edgartown, MA 02539
    • /14

      Est $2,704,037 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,926 Sq Ft

      30 Pond Ln, Vineyard Haven, MA 02568

      30 Pond Ln, Vineyard Haven, MA 02568
  • /41

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,424 Sq Ft

    19 Old Woods Rd, Chilmark, MA 02535

    Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

    Cheri Mason Landvest MV

    19 Old Woods Rd, Chilmark, MA 02535
  • /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
  • /6

    $430,000 Sold Jun 18, 2025

    • Land
    • 1.40 Acres
    • $307,143 per Acre
    • 0 Days On Market

    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

    Not listed in LINK.

    LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
    • /36

      Est $1,288,385 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,780 Sq Ft

      16 Rock Pond Rd, Vineyard Haven, MA 02568

      16 Rock Pond Rd, Vineyard Haven, MA 02568

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