
205 South Rd Chilmark — Photo 1 of 42
Recent Drop: $655,000
$4,995,000
Chilmark, MA 02575 — Chilmark
Beds
4
Baths
4.5
SqFt
5,402
Style
Single Family
Built
1940
CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.
* Analysis is based on 8 actively listed and recently sold comparable properties strictly within Chilmark, MA.
Water Heater
Was $5,350,000
Jul 30, 2026
MLS® 73495595
Was $5,650,000
May 14, 2026
MLS® 73495595
Apr 3, 2026
MLS® 73495595
2,718
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$173K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
8.4%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
164 housing units permitted in the last 12 months (+80% vs the prior 12 months) — 35 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 5,402 sq ft principal dwelling). Lot size: 260,924 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Tina Miller
Listing Office: Compass
MLS® Number: 73495595
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