$2,950,000

19 Old Woods Rd Chilmark, MA 02535

Chilmark Neighborhood

Estimated payment $19,447/month

Total Views 7,205
4 Beds
3 Baths
2,424 Sq Ft
$1,217 Price per Sq Ft

About This Home

Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his celebrated reputation as a leading American scene painter.” You can feel this history when you step inside. Anchored by a classic 1973 home and a classic shingle 1950s artist’s studio, the property is a rare find offering character, privacy, and pastoral beauty. The main house features an updated kitchen, a great room with vaulted ceilings and fireplace, a sitting room with a beach stone fireplace, 2 bedrooms and 2 baths. The oversized screened porch is the perfect spot to end the day. Once outside, the 14x20 pool and hot tub are surrounded by mature plantings, a stone patio and pergola. Nearby, the wisteria-covered patio provides yet another area to enjoy the surroundings. Next door, the detached studio with a full bath —originally built as a creative sanctuary in the 1950s—offers inspiring space for art, writing, or guest accommodations. Rolling hills and stone walls frame the landscape, evoking the casual elegance of old Chilmark. Whether you’re looking to restore, refresh or expand, this property is full of potential in a tranquil up-Island location. *The abutting parcel with two cottages was also part of the Benton family and are available for purchase.

Last Listed By

Cheri Mason

Landvest MV Listed on: 05/21/2025

Map

Home Details

Home Type

Single Family

Year Built

1973

Lot Details

0

Listing Details

  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Co List Office Mls Id: 786
  • Special Features: None
  • Year Built: 1973

Interior Features

  • Appliances: Stove: No, Washer: No
  • Has Basement: Crawlspace
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Total Bedrooms: 4
  • Fireplace Features: 3
  • Interior Amenities: Irr,OSh, Floor 1: The arched front door leads to a charming sitting room with antique beach stone fireplace, an updated kitchen, impressive great room with attached screened porch, 2 bedrooms and 2 baths all on the first floor., Floor 2: A narrow staircase leads to an artists loft, office or bedroom
  • Main Level Bedrooms: 3
  • Total Bedrooms: 8

Exterior Features

  • Pool Private: No
  • Foundation Details: Crawl space
  • Other Structures: There is a pool equipment building and a well house on the property. Next-door, a detached bedroom or studio with full bath, loft and rear deck. In addition, there is a large barn door garage in need of some love.

Garage/Parking

  • Parking Features: Ample

Utilities

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

Lot Info

  • Lot Size Sq Ft: 126324
  • Land Lease Expiration Date: 2026-03-06
  • Zoning: R3

Multi Family

  • Number Of Units Furnished: Unfurnished

Tax Info

  • Tax Annual Amount: 5364.06
  • Tax Lot: 73
  • Tax Map Number: 30
  • Tax Other Annual Assessment Amount: 1007000
  • Tax Year: 2025

Range of Values:

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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)

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Source: LINK (Vineyard)

MLS Number: 43314

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 $2,950,000, approximately $1,216 per square foot. This property was built in 1973. 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