19-C Old Woods Road

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.