Chilmark, MA 02535 16 South Road

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Presented By: Michele Casavant with Vineyard Village Realty -
  • MLS# 44181
  • 03/09/2026
  • Request Tour
  • Request Info
  • Beds • 4
  • Baths • 3
  • SQFT • 2,350

Home Details

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.
Presented By: Michele Casavant with Vineyard Village Realty -

Interior Features for 16 South Road

Bedrooms

Main Level Bedrooms2
Total Bedrooms4

Bathrooms

Half Baths

Other Interior Features

BasementNew full basement with laundry under the 1989 addition. Partial full basement with mechanical room under the original house, remainder is crawl.
Fireplace Featuresyes
Fireplace Y/NNo
Flooringhardwood and tile
Furnished Y/NUnfurnished
Interior AmenitiesAC, Ins, MiniSplit, Floor 1: 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., Floor 2: Two bedroom en-suites, each with their own bathroom., Floor 3: Attic space

General for 16 South Road

AppliancesStove: Thermador, Washer: yes
Building Area UnitsSquare Feet
CityChilmark
Full Baths3
HeatingPropane
Lot Size Square Feet69696
MLS Area5
Other StructuresLarge barn with electricity, two levels and garage area. Chicken coop and shed. Horse run-in barn with two stalls.
Property SubtypeSingle Family Residence
Property Type1 Family
SewerSeptic Tank
Standard StatusActive
StatusA
Tax Annual Amount4100
Tax Assessed Value905900
Tax Lot20
Tax Year2025
TaxOtherAnnualAssessmentAmount697800
Total Rooms8
UtilitiesCbl
ViewNone, Pasture
Year Built1885
Year Built Effective2018
ZoningRES

Exterior for 16 South Road

Building Area Total2350
Exterior AmenitiesDeck, Garden, Patio, Porch
Foundation Detailsmixed-parital poured concrete, partial granite
Frontage TypeNone
Lot FeaturesBoundary Line Agreement book 01373, page 0990, expansive large yard and field for horses, animals and gardneing
Lot Size Acres1.6
Lot Size Area1.6
Parking Featuresplenty of off street parking
Water SourceWell

Additional Details

Price History

Brian Skidmore

Price $2,395,000
MLS#44181
List Date 03/09/2026
Property Type Single Family
Phone 617.834.3227
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