2,453

Homes in ZIP Code 02535

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  • 15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    /42

    $4,250,000

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

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

    Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
  • 27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    /21

    $7,000 total monthly price

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

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt . 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

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • 6 Tabor Hills, Chilmark, MA 02535
    6 Tabor Hills, Chilmark, MA 02535
    6 Tabor Hills, Chilmark, MA 02535
    /43

    $2,100,000 Sold Nov 25, 2025

    • 1,968 Sq Ft
    • $1,067/SF
    • 50 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1993

    6 Tabor Hills, Chilmark, MA 02535

    Set on 3 acres of natural beauty, this 1968 s/f post-and-beam home offers a tranquil and inviting setting surrounded by stone walls, serene gardens, and the glacial erratic stones that distinguish the Chilmark landscape.The main residence features three levels of living. A chef's kitchen with a Viking gas range and pantry overlooks the open floor plan, awash in natural light with wide-plank

    Dawn Bellante Sandpiper Realty Inc

    6 Tabor Hills, Chilmark, MA 02535
    • 394 Lighthouse Rd, Aquinnah, MA 02535
      394 Lighthouse Rd, Aquinnah, MA 02535
      394 Lighthouse Rd, Aquinnah, MA 02535
      /58

      Est $7,061,096 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,945 Sq Ft

      394 Lighthouse Rd, Aquinnah, MA 02535

      394 Lighthouse Rd, Aquinnah, MA 02535
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /42

    $3,995,000

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

    96 Hammett Ln, Chilmark, MA 02535

    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
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /20

    $4,250 total monthly price

    • 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.

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • 20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    /37

    $6,550,000 Sold Nov 14, 2025

    • 3,355 Sq Ft
    • $1,952/SF
    • 46 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1993

    20 Eliot Ave, Chilmark, MA 02535

    Waterfront home on Stonewall Pond with Ocean Views. Nestled along the serene shores of Stonewall Pond, this waterfront home is located in one is Chilmark's most idyllic locations. This remarkable property offers an unparalleled living experience with breathtaking Atlantic Ocean views and exclusive access to Stonewall Beach. Step inside and be greeted by a seamless fusion of elegance and comfort.

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    20 Eliot Ave, Chilmark, MA 02535
    • 260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      /79

      Not Listed For Sale

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

      260 South Rd, Chilmark, MA 02535

      260 South Rd, Chilmark, MA 02535
  • 27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    /39

    $3,500,000

    • 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
  • 836 State Rd, Aquinnah, MA 02535
    836 State Rd, Aquinnah, MA 02535
    836 State Rd, Aquinnah, MA 02535
    /4

    $6,000 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • House for Rent

    836 State Rd, Aquinnah, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

    Karen Overtoom Karen M. Overtoom R.E.

    836 State Rd, Aquinnah, MA 02535
  • 3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    /48

    $1,775,000 Sold Nov 07, 2025

    • 1,728 Sq Ft
    • $1,027/SF
    • 170 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    3 Fulling Mill Rd, Chilmark, MA 02535

    Tucked away in a prime location just off Middle Road is this bright modern home offering the perfect blend of comfort and style. The main level features a large bedroom or first-floor office and a full bath, while the upper floor boasts two additional bedrooms and a beautifully appointed bathroom with a steam shower and double vanity. The open concept living and dining areas flow effortlessly

    Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
    • 4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      /75

      Est $3,405,343 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,362 Sq Ft

      4 Tilton Rd, Chilmark, MA 02535

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

    $4,950,000

    • 5 Beds
    • 4 Baths
    • 3,413 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 historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
  • 5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    /8

    $16,000 total monthly price

    • 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
  • 29 Oxcart Rd, Aquinnah, MA 02535
    29 Oxcart Rd, Aquinnah, MA 02535
    29 Oxcart Rd, Aquinnah, MA 02535
    /31

    $3,750,000 Sold Oct 31, 2025

    • 1,274 Sq Ft
    • $2,943/SF
    • 380 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2009

    29 Oxcart Rd, Aquinnah, MA 02535

    Waterfront beach house on Dogfish Bar in Aquinnah. Take in the beauty of this gem of a location with rolling dunes, waterviews and immense sunsets! This property is one of only a few homes on this stretch of private and preserved beach. This 2009 contemporary beach house offers a reverse floor plan with the entire top floor as the living area, kitchen & dining, and more windows than walls to

    Michelle Kelly Tea Lane Associates

    29 Oxcart Rd, Aquinnah, MA 02535
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,241,450 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,386 Sq Ft

      7 the Aerie, Chilmark, MA 02535

      7 the Aerie, Chilmark, MA 02535
  • 124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    /34

    $4,950,000

    • 5 Beds
    • 4.5 Baths
    • 3,413 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 historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • 849 State Rd Unit 1, Aquinnah, MA 02535
    849 State Rd Unit 1, Aquinnah, MA 02535
    849 State Rd Unit 1, Aquinnah, MA 02535
    /8

    $3,300 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • House for Rent

    849 State Rd Unit 1, Aquinnah, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

    Karen Overtoom Karen M. Overtoom R.E.

    849 State Rd Unit 1, Aquinnah, MA 02535
  • 12 Squibnocket Rd, Chilmark, MA 02535
    12 Squibnocket Rd, Chilmark, MA 02535
    /2

    $5,900,000 Sold Oct 31, 2025

    • 3,143 Sq Ft
    • $1,877/SF
    • 0 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 1849

    12 Squibnocket Rd, Chilmark, MA 02535

    Not Listed in LINK

    LINK Email Cache LINK

    12 Squibnocket Rd, Chilmark, MA 02535
    • 1 Skippers View Ln, Aquinnah, MA 02535
      1 Skippers View Ln, Aquinnah, MA 02535
      1 Skippers View Ln, Aquinnah, MA 02535
      /22

      Est $4,493,868 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,905 Sq Ft

      1 Skippers View Ln, Aquinnah, MA 02535

      1 Skippers View Ln, Aquinnah, MA 02535
  • 60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    /49

    $6,490,000 Pending

    • 6 Beds
    • 8 Baths
    • 5,660 Sq Ft

    60 Meetinghouse Rd, Chilmark, MA 02535

    This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

    Jim Feiner Feiner Real Estate

    60 Meetinghouse Rd, Chilmark, MA 02535
  • 3 E Pasture Ln, Aquinnah, MA 02535
    3 E Pasture Ln, Aquinnah, MA 02535
    3 E Pasture Ln, Aquinnah, MA 02535
    /11

    $20,000 total monthly price

    • 4 Beds
    • 4.5 Baths
    • 2,306 Sq Ft
    • House for Rent

    3 E Pasture Ln, Aquinnah, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

    Karen Overtoom Karen M. Overtoom R.E.

    3 E Pasture Ln, Aquinnah, MA 02535
  • 94 Menemsha Inn Rd, Chilmark, MA 02535
    94 Menemsha Inn Rd, Chilmark, MA 02535
    94 Menemsha Inn Rd, Chilmark, MA 02535
    /44

    $8,178,500 Sold Oct 27, 2025

    • 4,104 Sq Ft
    • $1,993/SF
    • 38 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2001

    94 Menemsha Inn Rd, Chilmark, MA 02535

    Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large

    Julianna Flanders Flanders Real Estate

    94 Menemsha Inn Rd, Chilmark, MA 02535
    • 8 Harpoon Hollow, Aquinnah, MA 02535
      8 Harpoon Hollow, Aquinnah, MA 02535
      8 Harpoon Hollow, Aquinnah, MA 02535
      /30

      Est $1,802,511 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,046 Sq Ft

      8 Harpoon Hollow, Aquinnah, MA 02535

      8 Harpoon Hollow, Aquinnah, MA 02535
  • 18 Homeward Way, Chilmark, MA 02535
    18 Homeward Way, Chilmark, MA 02535
    18 Homeward Way, Chilmark, MA 02535
    /24

    $4,695,000 Pending

    • 5 Beds
    • 2.5 Baths
    • 3,885 Sq Ft

    18 Homeward Way, Chilmark, MA 02535

    Welcome to 18 Homeward Way — a peaceful Chilmark retreat tucked off scenic North Road, just minutes from the storied fishing village of Menemsha. This rare 15-acre offering includes two buildable parcels, creating an extraordinary opportunity for a Vineyard compound. The impeccably maintained residence, built in 1986, radiates classic Vineyard charm. Its thoughtful single-level layout fosters

    Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
  • 33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    /8

    $4,500 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • 9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    /39

    $2,225,000 Sold Oct 24, 2025

    • 2,968 Sq Ft
    • $750/SF
    • 98 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1994

    9 Beetlebung Grove Way, Chilmark, MA 02535

    Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

    Stephanie Roache Donnelly + Co.

    9 Beetlebung Grove Way, Chilmark, MA 02535
    • 51 Blueberry Ridge Ln, Chilmark, MA 02535
      51 Blueberry Ridge Ln, Chilmark, MA 02535
      51 Blueberry Ridge Ln, Chilmark, MA 02535
      /23

      Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 2,229 Sq Ft

      51 Blueberry Ridge Ln, Chilmark, MA 02535

      51 Blueberry Ridge Ln, Chilmark, MA 02535
  • 146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo Rd, Chilmark, MA 02535
    /37

    $4,850,000 Pending

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft

    146 Quansoo Rd, Chilmark, MA 02535

    Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

    Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
  • 6 Briar Path, Aquinnah, MA 02535
    6 Briar Path, Aquinnah, MA 02535
    6 Briar Path, Aquinnah, MA 02535
    /15

    $5,000 total monthly price

    • 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
  • 49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    /9

    $1,500,000 Sold Oct 20, 2025

    • Land
    • 3.9 Acres
    • $384,615 per Acre

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

    3.9-acre parcel in a very distinguished Chilmark neighborhood. The property comes with deeded access to Tisbury Great Pond via the boat landing just 1/3 of a mile away. From there the Atlantic Ocean is just a boat ride away.

    Mark Jenkins Wallace & Co. Sotheby's

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    • 6 Beach Plum Way, Aquinnah, MA 02535
      6 Beach Plum Way, Aquinnah, MA 02535
      6 Beach Plum Way, Aquinnah, MA 02535
      /56

      Est $3,790,555 Not Listed For Sale

      • 7 Beds
      • 5.5 Baths
      • 4,875 Sq Ft

      6 Beach Plum Way, Aquinnah, MA 02535

      6 Beach Plum Way, Aquinnah, MA 02535
  • 4 Nomans Watch Rd, Aquinnah, MA 02535
    4 Nomans Watch Rd, Aquinnah, MA 02535
    4 Nomans Watch Rd, Aquinnah, MA 02535
    /35

    $3,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,686 Sq Ft

    4 Nomans Watch Rd, Aquinnah, MA 02535

    Perched on 2.7 acres in one of Aquinnah’s most breathtaking settings, this beautifully sited coastal retreat offers sweeping views over the Atlantic and Noman’s Land from its elevated position. Designed to embrace the light and scenery, the main level features an open living/dining/kitchen area wrapped in walls of windows—an airy, sun-soaked space where ocean views take center stage. The

    Jen O'Hanlon Compass | The O'Hanlon Group

    4 Nomans Watch Rd, Aquinnah, MA 02535
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /8

    $8,000 total monthly price

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

    56 Chilmark Rd, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! 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 land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    /16

    $475,000 Sold Oct 20, 2025

    • Land
    • 0 Acre
    • 11 Days On Market

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535

    Spectacular beach lot at Quansoo. This is the ultimate amenity. Ownership provides access to one of the most stunning beaches on the entire eastern seaboard. On one side is the majestic Atlantic Ocean and on the other the calm waters of Tisbury Great Pond where kids can catch crabs and play safely as you watch. Skip the lines and crowds at other beaches - come and go as you please for sun, sand,

    Mark Jenkins Wallace & Co. Sotheby's

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    • 7 Tar Barrel Rd, Aquinnah, MA 02535
      7 Tar Barrel Rd, Aquinnah, MA 02535
      7 Tar Barrel Rd, Aquinnah, MA 02535
      /41

      Est $1,815,061 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,803 Sq Ft

      7 Tar Barrel Rd, Aquinnah, MA 02535

      7 Tar Barrel Rd, Aquinnah, MA 02535
  • 34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    /21

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

    Peyton Wallace Studio Realty

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
  • 6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    /26

    $50,700 total monthly price

    • 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
  • 25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    /37

    $7,289,000 Sold Oct 15, 2025

    • 3,777 Sq Ft
    • $1,930/SF
    • 77 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1988

    25 Osprey Ln, Chilmark, MA 02535

    Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary

    Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • 391 Middle Rd, Chilmark, MA 02535
      391 Middle Rd, Chilmark, MA 02535
      391 Middle Rd, Chilmark, MA 02535
      /34

      Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 3,859 Sq Ft

      391 Middle Rd, Chilmark, MA 02535

      391 Middle Rd, Chilmark, MA 02535

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Massachusetts Dukes County Chilmark 02535

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