$3,400,000

19 Old Woods Rd Chilmark, MA 02535

Chilmark Neighborhood

Estimated payment $22,232/month

Total Views 4,577
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 Listed on: 05/21/2025

Map

Property Details

Home Type

Multi-Family

Year Built

1950

Lot Details

0

Listing Details

  • Property Sub Type: Multi Family
  • Property Type: Multi Family
  • Co List Office Mls Id: 786
  • Special Features: None
  • Year Built: 1950

Interior Features

  • Appliances: Stove: Yes - gas, Washer: No
  • Has Basement: Crawl space
  • Full Bathrooms: 2
  • Total Bedrooms: 5
  • Fireplace Features: 2
  • Interior Amenities: Irr,OSh,WdStove, Floor 1: 2 bedrooms, a great room and kitchen on a single level, deck and outdoor shower.
  • Main Level Bedrooms: 2
  • Total Bedrooms: 11

Exterior Features

  • Pool Private: No
  • Foundation Details: Crawl space or bulkhead
  • Other Structures: Shed

Garage/Parking

  • Parking Features: Yes

Utilities

  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Well

Lot Info

  • Lot Size Sq Ft: 544500
  • Land Lease Expiration Date: 2026-03-04
  • Zoning: R3

Multi Family

  • Number Of Units Furnished: Unfurnished

Tax Info

  • Tax Annual Amount: 5909.83
  • Tax Lot: 75
  • Tax Map Number: 30
  • Tax Other Annual Assessment Amount: 1770400
  • Tax Year: 2025

Range of Values:

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Average Value
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List 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

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 1950. 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