205 South Rd Chilmark — Photo 1 of 42
Recent Drop: $655,000
$4,995,000
Investment Analysis — 205 South Rd
Chilmark, MA 02575 — Chilmark
Based on HUD Small Area Fair Market Rent for Dukes County, MA, a 4-bedroom in 02575 carries an estimated $4,060/mo in gross rent — about a 0.46% cap rate and $23,127/yr in estimated NOI at the $4,995,000 list price. Adjust every assumption in the calculator below.
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.
ADU Potential
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater
Geography
Property History
$4,995,000
Was $5,350,000
Jul 30, 2026
MLS® 73495595
$5,350,000
Was $5,650,000
May 14, 2026
MLS® 73495595
$5,650,000
Apr 3, 2026
MLS® 73495595
Listing Agent: Tina Miller
Listing Office: Compass
MLS® Number: 73495595
