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Chilmark Homes for Sale

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  • 49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    /51

    $5,295,000

    • 5 Beds
    • 4 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

    Meg Bodnar Tea Lane Associates

    49 Gosnold's Way, Chilmark, MA 02535
  • 34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    /42

    $8,750,000

    • 5 Beds
    • 3 Baths
    • 2,269 Sq Ft

    34 Edys Island Way, Chilmark, MA 02535

    Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the Southeast,

    Jill Napior

    34 Edys Island Way, Chilmark, MA 02535
  • 146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo Rd, Chilmark, MA 02535
    /38

    $5,475,000

    • 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
  • 25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    /31

    $2,450,000

    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    25 Fulling Mill Rd, Chilmark, MA 02535

    Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    25 Fulling Mill Rd, Chilmark, MA 02535
  • 345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    /23

    $1,695,000

    • 5 Beds
    • 5 Baths
    • 2,316 Sq Ft

    345 North Rd, Chilmark, MA 02535

    Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    345 North Rd, Chilmark, MA 02535
Massachusetts Marthas Vineyard Chilmark

Real Estate & Homes for Sale in Chilmark, Marthas Vineyard

About Chilmark

Chilmark, located in the up-island region of Martha’s Vineyard, is characterized by its serene, rural landscape and expansive rolling hills reminiscent of Ireland. This quiet town is known for its privacy, with homes set on large lots of at least three acres, often at the end of private dirt roads. The area lacks a downtown district and gastropubs, offering instead the tranquility of mighty-waved beaches like Lucy Vincent Beach, exclusive to town residents. The neighborhood is home to gray-shingled Cape Cod-style houses and vast family compounds, reflecting its reputation for high property values, though it maintains one of the lowest property tax rates on the island. Menemsha, a quaint fishing village within Chilmark, features markets selling fresh seafood and offers scenic hikes along Menemsha Hills. Residents enjoy local amenities such as the Chilmark General Store, known for its pizza and locally sourced goods, and the Yard, a performing arts venue. Chilmark School serves younger children with a unique multi-age classroom approach, while older students attend Martha’s Vineyard Regional High School, which provides a range of educational programs. The town is about a 30-minute drive from Edgartown and Oak Bluffs, with Martha’s Vineyard Airport just 15 minutes away, offering both year-round and seasonal flights.

Learn more about living in Chilmark

Frequently Asked Questions

Is Chilmark a good place to live?
Chilmark is a good place to live. Chilmark is considered very car-dependent and somewhat bikeable. Chilmark is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Chilmark has 1 park for recreational activities. It is sparse in population with 0.1 people per acre and a median age of 56. The average household income is $161,487 which is above the national average. College graduates make up 64.4% of residents. A majority of residents in Chilmark are home owners, with 20.4% of residents renting and 79.6% of residents owning their home. A local real estate agent serving Chilmark can help you decide if this neighborhood is the right one for you. Learn more on our Chilmark neighborhood guide.
Is Chilmark, MA a safe neighborhood?
Chilmark, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Chilmark?
The median home price in Chilmark is $5,295,000. If you put a 20% down payment of $1,059,000 and had a 30-year fixed mortgage with an interest rate of 6.81%, your estimated principal and interest payment would be $27,640 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $1M a year to afford the median home price in Chilmark. The average household income in Chilmark is $161K.
What are the best public schools in Chilmark?
The best public schools that serve Chilmark are:
What are the most popular zip codes in Chilmark, Marthas Vineyard, MA?
The most popular zip codes in Chilmark, Marthas Vineyard, MA include 02649, 02536, 02540, 02568 and 02740.
What are the most popular neighborhoods near Chilmark, Marthas Vineyard, MA?
The most popular neighborhoods near Chilmark, Marthas Vineyard, MA are West Tisbury, Tisbury, Edgartown, Oak Bluffs and Vineyard Haven.

Home Trends in Chilmark, MA

On average, homes in Chilmark, Marthas Vineyard sell after 197 days on the market compared to the national average of 47 days. The average sale price for homes in Chilmark, Marthas Vineyard over the last 12 months is $6,400,000, up 101% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)
$5,862,500
Median Single Family Price
$5,295,000
Average Price Per Sq Ft
$1,569
Number of Homes for Sale
5
Last 12 months Home Sales
6
Months of Supply
10.00
Median List Price
$5,295,000
Median Discount From 1st List Price
23%
Median Home Sale Price YoY Change
84%
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