1,747

Chilmark Homes

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  • 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 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
  • 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

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

    $6,000 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. 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
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,272,460 Not Listed For Sale

      7 the Aerie, Chilmark, MA 02535

      • 3 Beds
      • 1.5 Baths
      • 1,386 Sq Ft
      • Built 1989
      7 the Aerie, Chilmark, MA 02535

      Last Sold Summary

      • 21% Above List Price
      • $1,353/SF
      • 11 Days On Market

      Last Sold Price $1,875,000

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • 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 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
  • 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
    • 82 South Rd, Chilmark, MA 02535
      82 South Rd, Chilmark, MA 02535
      82 South Rd, Chilmark, MA 02535
      /26

      Est $2,080,292 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

      • 14% Above List Price
      • $983/SF
      • 10 Days On Market

      Last Sold Price $1,830,000

      Last Listing Agent Meg Bodnar Tea Lane Associates

  • 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
  • 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
  • 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 $6,526,503

    Last Listing Agent Deb Hancock Hancock Real Estate

    25 Osprey Ln, 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.

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

    $3,990,000 Pending

    • 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
  • 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 master

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, 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
    • 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

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

    $900,000 Sold Sep 17, 2025

    45 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

    45 Quenames Rd Unit 30-02, Chilmark, MA 02535
    • 1 Carroll Ln, Chilmark, MA 02535
      1 Carroll Ln, Chilmark, MA 02535
      1 Carroll Ln, Chilmark, MA 02535
      /5

      Est $602,648 Not Listed For Sale

      1 Carroll Ln, Chilmark, MA 02535

      • 2 Beds
      • 1 Bath
      • 708 Sq Ft
      • Built 1920
      1 Carroll Ln, Chilmark, MA 02535

      Last Sold Summary

      • 34% Above List Price
      • $636/SF
      • 21 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Nicholas Korba Landmarks at TODAY Real Estate

  • 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
  • 224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    /3

    $13,200 total monthly price

    • 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
  • 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
    • 7 Flanders Ln, Chilmark, MA 02535
      7 Flanders Ln, Chilmark, MA 02535
      7 Flanders Ln, Chilmark, MA 02535
      /29

      Est $1,719,593 Not Listed For Sale

      7 Flanders Ln, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1954
      7 Flanders Ln, Chilmark, MA 02535

      Last Sold Summary

      • 2% Above List Price
      • $1,400/SF
      • 4 Days On Market

      Last Sold Price $1,680,000

      Last Listing Agent Meg Bodnar Tea Lane Associates

  • 6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    /16

    $3,200,000

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
  • 2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    /33

    $22,000 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • 3 Tennis Ln, Chilmark, MA 02535
    3 Tennis Ln, Chilmark, MA 02535
    /2

    $3,772,500 Sold May 29, 2025

    3 Tennis Ln, Chilmark, MA 02535

    • 4 Beds
    • 4.5 Baths
    • 3,234 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Below List Price
    • $1,167/SF
    • 0 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    3 Tennis Ln, Chilmark, MA 02535
    • 12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      /13

      Est $1,489,144 Not Listed For Sale

      12 Harbor Hill Rd, Chilmark, MA 02535

      • 1 Bed
      • 1 Bath
      • 640 Sq Ft
      • Built 1955
      12 Harbor Hill Rd, Chilmark, MA 02535

      Last Sold Summary

      • 6% Above List Price
      • $2,188/SF
      • 0 Days On Market

      Last Sold Price $1,400,000

      Last Listing Agent Deb Hancock Hancock Real Estate

  • 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
  • 31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    /20

    $16,800 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, 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

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

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

    Last Sold Summary

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

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    • 15 Red Valley Rd, Chilmark, MA 02535
      15 Red Valley Rd, Chilmark, MA 02535
      15 Red Valley Rd, Chilmark, MA 02535
      /34

      Est $5,273,817 Not Listed For Sale

      15 Red Valley Rd, Chilmark, MA 02535

      • 5 Beds
      • 4 Baths
      • 2,373 Sq Ft
      • Built 1954
      15 Red Valley Rd, Chilmark, MA 02535

      Last Sold Summary

      • 3% Above List Price
      • $2,149/SF
      • 31 Days On Market

      Last Sold Price $5,100,000

      Last Listing Agent Jill Napior Tea Lane Associates

  • 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
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    /31

    $40,000 total monthly price

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • 10 N Abels Hill Rd, Chilmark, MA 02535
    10 N Abels Hill Rd, Chilmark, MA 02535
    10 N Abels Hill Rd, Chilmark, MA 02535
    /22

    $1,607,000 Sold Jul 10, 2025

    10 N Abels Hill Rd, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,850 Sq Ft
    • Built 1978

    Last Sold Summary

    • 39% Below List Price
    • $564/SF
    • 354 Days On Market

    Current Estimated Value $1,998,493

    Last Listing Agent Elissa Lash Tea Lane Associates

    10 N Abels Hill Rd, Chilmark, MA 02535
    • 1 Pond Mark, Chilmark, MA 02535
      1 Pond Mark, Chilmark, MA 02535
      1 Pond Mark, Chilmark, MA 02535
      /18

      Est $3,749,483 Not Listed For Sale

      1 Pond Mark, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1955
      1 Pond Mark, Chilmark, MA 02535

      Last Sold Summary

      • 5% Below List Price
      • $3,002/SF
      • 466 Days On Market

      Last Sold Price $3,950,000

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

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County Marthas Vineyard Chilmark

Real Estate & Homes

Learn more about living in Chilmark

Home Trends in Chilmark, MA

On average, homes in Chilmark, Marthas Vineyard sell after 85 days on the market compared to the national average of 54 days. The median sale price for homes in Chilmark, Marthas Vineyard over the last 12 months is $4,350,000, up 102% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$4,350,000
Median Single Family Sale Price
$2,825,000
Average Price Per Sq Ft
$1,852
Number of Homes for Sale
13
Last 12 months Home Sales
27
Months of Supply
5.80
Median List Price
$3,025,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
102%
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