$3,400,000

19 Old Woods Rd Chilmark, MA 02535

Chilmark Neighborhood

Estimated payment $22,431/month

Total Views 1,046
5 Beds
2 Baths
3,133 Sq Ft
$1,085 Price per Sq Ft

About This Home

Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy with the neighboring property at its end. Each house reflects the simple beauty of its era, open living spaces, and a relaxed, unpretentious spirit. Whether you choose to update, preserve, or reimagine, these homes are rich with potential with ample space for expansion. The land is natural, wooded, sloping and steeped in Chilmark’s rural charm. This is a unique opportunity to own a multi-home compound with a 50-year family history. *The house with pool, studio and garage at the end of the road, also owned by the Benton family, is also available for sale.

Listing Agent

Cheri Mason

Landvest MV

Map

Range of Values:

Collateral Analytics

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ICE

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First American

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Quantarium

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Average Value
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

Date Event Price Change Sq Ft Price
05/21/2025 05/21/25 For Sale $2,950,000 -13.2% $1,217 / Sq Ft
05/21/2025 05/21/25 For Sale $3,400,000 -- $1,085 / Sq Ft
Source: LINK (Vineyard)

Source: LINK (Vineyard)

MLS Number: 43319

APN: CHIL M:0030 B:0075 L:

Massachusetts Dukes County Chilmark 02535 Chilmark

19 Old Woods Rd, Chilmark, MA

Homes for Sale in Chilmark, MA

This home is located at 19 Old Woods Rd, Chilmark, MA 02535 and is currently priced at $3,400,000, approximately $1,085 per square foot. This property was built in 1948. 19 Old Woods Rd is a home located in Dukes County with nearby schools including Martha's Vineyard Regional High School.

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Nearby Homes
Listing Agent
Cheri Mason
Landvest MV