2,450

Homes in ZIP Code 02535

Section Image Section Image
  • 43 N Slope Ln, Chilmark, MA 02535
    43 N Slope Ln, Chilmark, MA 02535
    43 N Slope Ln, Chilmark, MA 02535
    /31

    $1,799,999

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    43 N Slope Ln, Chilmark, MA 02535

    Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

    Agent Photo

    Barbara O'Hara

    NorthStar Real Estate, LLC

    (508) 850-0854

    43 N Slope Ln, 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 per month

    • 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
  • 00 Eliot Ave Unit 17, Chilmark, MA 02535
    00 Eliot Ave Unit 17, Chilmark, MA 02535
    00 Eliot Ave Unit 17, Chilmark, MA 02535
    /3

    $105,000 Sold Sep 05, 2025

    00 Eliot Ave Unit 17, Chilmark, MA 02535

    • Land
    • 0.7 Acre
    • $150,000 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 29 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    00 Eliot Ave Unit 17, 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

      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

      • $1,671/SF
      • 109 Days On Market

      Last Sold Price $4,350,000

      Last Listing Agent Jill Napior Tea Lane Associates

  • 78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    /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
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /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
  • 2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    /42

    $9,725,000 Sold Apr 24, 2025

    2 Squibnocket Rd, Chilmark, MA 02535

    • 6 Beds
    • 5.5 Baths
    • 5,808 Sq Ft
    • Built 2008

    Last Sold Summary

    • 22% Below List Price
    • $1,674/SF
    • 295 Days On Market

    Last Listing Agent Tina Miller Donnelly + Co.

    2 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 $4,418,187 Not Listed For Sale

      1 Skippers View Ln, Aquinnah, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,905 Sq Ft
      • Built 2001
      1 Skippers View Ln, Aquinnah, MA 02535

      Last Sold Summary

      • 3% Below List Price
      • $1,575/SF
      • 0 Days On Market

      Last Sold Price $4,575,000

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

  • 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

    $3,950,000 Pending

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

    $6,000 per month

    • 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
  • 0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535
    0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535
    0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535
    /3

    $435,000 Sold Jul 23, 2025

    0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535

    • Land
    • 0.3 Acre
    • $1,457,775 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 96 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535
    • 8 Harpoon Hollow, Aquinnah, MA 02535
      8 Harpoon Hollow, Aquinnah, MA 02535
      8 Harpoon Hollow, Aquinnah, MA 02535
      /30

      Est $1,802,497 Not Listed For Sale

      8 Harpoon Hollow, Aquinnah, MA 02535

      • 3 Beds
      • 3 Baths
      • 2,046 Sq Ft
      • Built 1940
      8 Harpoon Hollow, Aquinnah, MA 02535

      Last Sold Summary

      • 13% Above List Price
      • $782/SF
      • 179 Days On Market

      Last Sold Price $1,600,000

      Last Listing Agent Brenda Galligan Karen M. Overtoom R E

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

    $3,950,000 Under Contract

    • 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 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
  • 654 Lighthouse Rd, Aquinnah, MA 02535
    654 Lighthouse Rd, Aquinnah, MA 02535
    654 Lighthouse Rd, Aquinnah, MA 02535
    /29

    $1,470,000 Sold Mar 24, 2026

    654 Lighthouse Rd, Aquinnah, MA 02535

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1972

    Last Sold Summary

    • 22% Below List Price
    • $919/SF
    • 195 Days On Market

    Current Estimated Value $2,186,920

    Last Listing Agent Heidi Vanderhoop Tea Lane Associates

    654 Lighthouse Rd, Aquinnah, MA 02535
    • 82 South Rd, Chilmark, MA 02535
      82 South Rd, Chilmark, MA 02535
      82 South Rd, Chilmark, MA 02535
      /26

      Est $1,935,899 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

      • 6% Above List Price
      • $983/SF
      • 10 Days On Market

      Last Sold Price $1,830,000

      Last Listing Agent Meg Bodnar Tea Lane Associates

  • 85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    /37

    $7,950,000

    • 5 Beds
    • 7 Baths
    • 4,531 Sq Ft

    85 Reservoir Rd, Vineyard Haven, MA 02568

    Nestled within Seven Gates Farm, one of Martha’s Vineyard’s most storied and scenic communities, this 26.5-acre estate features a beautifully renovated farmhouse blending modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property also includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    85 Reservoir Rd, Vineyard Haven, MA 02568
  • 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 per month

    • 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
  • 00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    /7

    $650,000 Sold Aug 14, 2025

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

    • Land
    • 0.2 Acre
    • $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
    • 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

      51 Blueberry Ridge Ln, Chilmark, MA 02535

      • 6 Beds
      • 3.5 Baths
      • 2,229 Sq Ft
      • Built 1989
      51 Blueberry Ridge Ln, Chilmark, MA 02535

      Last Sold Summary

      • $1,032/SF
      • 11 Days On Market

      Last Sold Price $2,300,000

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /38

    $3,995,000

    • 3 Beds
    • 3.5 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
  • 3 E Pasture Ln, Aquinnah, MA 02535
    3 E Pasture Ln, Aquinnah, MA 02535
    3 E Pasture Ln, Aquinnah, MA 02535
    /11

    $20,000 per month

    • 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
  • 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

    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

    Current Estimated Value $6,853,287

    Last Listing Agent Deb Hancock Hancock Real Estate

    25 Osprey Ln, 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 $3,815,089 Not Listed For Sale

      6 Beach Plum Way, Aquinnah, MA 02535

      • 7 Beds
      • 5.5 Baths
      • 4,875 Sq Ft
      • Built 1996
      6 Beach Plum Way, Aquinnah, MA 02535

      Last Sold Summary

      • 2% Above List Price
      • $764/SF
      • 21 Days On Market

      Last Sold Price $3,725,000

      Last Listing Agent Meg Bodnar Tea Lane Associates

  • 308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    /40

    $7,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, 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 per month

    • 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
  • 0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    /22

    $435,000 Sold Aug 26, 2025

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

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 18 Days On Market

    Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

    0 Quansoo Beach Lot Unit 53 43599, 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 $1,967,245 Not Listed For Sale

      7 Tar Barrel Rd, Aquinnah, MA 02535

      • 3 Beds
      • 3 Baths
      • 1,803 Sq Ft
      • Built 1998
      7 Tar Barrel Rd, Aquinnah, MA 02535

      Last Sold Summary

      • 9% Above List Price
      • $998/SF
      • 0 Days On Market

      Last Sold Price $1,800,000

      Last Listing Agent Heidi Vanderhoop Tea Lane Associates

  • 85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    /42

    $7,950,000

    • 5 Beds
    • 7 Baths
    • 4,531 Sq Ft

    85 Reservoir Rd, Vineyard Haven, MA 02568

    Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

    Alyssa Halisky Wallace & Co. Sotheby's

    85 Reservoir Rd, Vineyard Haven, MA 02568
  • 6 Briar Path, Aquinnah, MA 02535
    6 Briar Path, Aquinnah, MA 02535
    6 Briar Path, Aquinnah, MA 02535
    /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
  • 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

    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 $3,466,251

    Last Listing Agent Michelle Kelly Tea Lane Associates

    29 Oxcart Rd, Aquinnah, 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

      391 Middle Rd, Chilmark, MA 02535

      • 6 Beds
      • 4.5 Baths
      • 3,859 Sq Ft
      • Built 1941
      391 Middle Rd, Chilmark, MA 02535

      Last Sold Summary

      • $1,581/SF
      • 38 Days On Market

      Last Sold Price $6,100,000

      Last Listing Agent Jill Napior Tea Lane Associates

  • 64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    /43

    $14,500,000

    • 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
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /8

    $8,000 per month

    • 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 master

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    /2

    $900,000 Sold Sep 17, 2025

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535

    • Land
    • 3.05 Acres
    • $295,082 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 83 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    • 50 Campbell Rd, Vineyard Haven, MA 02568
      50 Campbell Rd, Vineyard Haven, MA 02568
      50 Campbell Rd, Vineyard Haven, MA 02568
      /23

      Est $2,052,201 Not Listed For Sale

      50 Campbell Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,370 Sq Ft
      • Built 1994
      50 Campbell Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Above List Price
      • $1,460/SF
      • 16 Days On Market

      Last Sold Price $2,000,000

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • 47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    /7

    $1,575,000

    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    47 Quenames Rd, Chilmark, MA 02535

    On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

    Dawn Bellante Sandpiper Realty, Inc.

    47 Quenames Rd, 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 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
  • 0 North Rd Unit 40 43533, Aquinnah, MA 02535
    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    /2

    $60,000 Sold Jul 01, 2025

    0 North Rd Unit 40 43533, Aquinnah, MA 02535

    • Land
    • 0 Acre

    Last Sold Summary

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    • 71 Runner Rd, Vineyard Haven, MA 02568
      71 Runner Rd, Vineyard Haven, MA 02568
      71 Runner Rd, Vineyard Haven, MA 02568
      /6

      Est $3,054,777 Not Listed For Sale

      71 Runner Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,935 Sq Ft
      • Built 1982
      71 Runner Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7% Below List Price
      • $1,703/SF
      • 0 Days On Market

      Last Sold Price $3,295,000

      Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County Chilmark 02535

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group