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

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

OTHER BUILDINGS
Array

SECOND DWELLING
P/Sd

PARKING
plenty of off street parking

Single Family Residence
Chilmark
16 South Road
$2,500,000.00


LINK ID: 44181
Bedrooms: 4
Baths: 3
Rooms: 8
Living Space: 2350
Acreage: 1.6000
Water Frontage: None
1st Floor Bedrooms 2
Outdoor Spaces: Deck, Garden, Patio, Porch
Features: AC,Ins,MiniSplit
Year Built: 1885
Year Renovated: 2018
Second Dwelling: Existing
Zoning: RES
Water: Well
Sewer: Septic Tank
Lead Paint: Unknown
Foundation : mixed-parital poured concrete
Heat: Propane
Fireplaces: yes
Yard Type: Boundary Line Agreement book 01373, page 0990. expansive large yard and field for horses, animals and gardneing
Flooring: hardwood and tile
Stove: Thermador
Washer: yes
TV: Cable