16 South Road, Chilmark

Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly pastoral sensibility. A classic barn, two run-in horse stalls, a fenced field, and a coop support equestrian pursuits or a small gentleman’s farm—an increasingly uncommon offering in Chilmark at this price point. The open acreage invites outdoor living, from summer entertaining and gardening to quiet enjoyment of the surrounding landscape and privacy. Inside, the home balances antique charm with thoughtful updates. Four bedrooms and three full baths include two main-level bedrooms and two second-floor en-suite guest rooms, creating a comfortable and flexible layout for hosting family and friends. Living spaces are warm and inviting, with a masonry double fireplace, preserved period details, and an updated kitchen and baths. Recent improvements include HVAC, windows, insulation, and a five-bedroom septic system, offering flexibility for future expansion and barn renovation. Located steps from West Tisbury village, Alleys General Store, the library, the Yoga Barn, the Grange Hall and nearby conservation trails, the setting combines convenience with the privacy and natural beauty that define Chilmark. A distinctive Vineyard offering with uncommon versatility—equally suited as a summer retreat, year-round residence, or small-scale farmstead.

First Floor

Front and side foyer, two lounge areas, one with a masonry fireplace, cathedral ceiling and oversized for dining. A kitchen with a cathedral ceiling, and kitchen island, a full bath. A breaze way for additional storage of shoes, coats and sporting equipment. Two bedrooms.

Second Floor

Two bedroom en-suites, each with their own bathroom.

Third Floor

Attic space

Basement

New full basement with laundry under the 1989 addition. Partial full basement with mechanical room under the original house, remainder is crawl.

Parking

plenty of off street parking

Other Buildings

Large barn with electricity, two levels and garage area. Chicken coop and shed. Horse run-in barn with two stalls.