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I'm Andrew Goldberg, a Boston real estate advisor specializing in first-time buyers across Greater Boston. I guide you A to Z—from first search to closing day.

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Commonwealth Standard Realty Advisors

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Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 205 South Rd, Chilmark, MA 02575
Active
144 Days on market
205 South Rd Chilmark — Photo 1 of 42

205 South Rd Chilmark — Photo 1 of 42

Recent Drop: $655,000

$5,650,000
$4,995,000

$4,995,000

205 South Rd, Chilmark, MA 02575

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$925/sqft
Local Avg (Chilmark)$1747/sqft
47% BelowMarket Average

* Analysis is based on 8 actively listed and recently sold comparable properties strictly within Chilmark, MA.

Property Details

Financials

Original Price$5,650,000
Annual Taxes$13,900

Parking

Garage3
Off-Street11

Interior Specifications

Total Rooms9
Fireplaces1
Flooring--
BasementFull, Partially Finished

Climate & Utilities

HeatingRadiant, Heat Pump
CoolingHeat Pump
WaterPrivate
SewerInspection Required for Sale

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter
ZoningRES

Property & Lot

Acres5.99
SqFt Lot260,924
Lot FeaturesWooded, Cleared, Gentle Sloping

Amenities & Appliances

Water Heater

Geography

Property History

Price Drop
$4,995,000

Was $5,350,000

Jul 30, 2026

MLS® 73495595

Price Drop
$5,350,000

Was $5,650,000

May 14, 2026

MLS® 73495595

Listed
$5,650,000

Apr 3, 2026

MLS® 73495595

Population

2,718

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$173K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

8.4%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Dukes County

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)

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.

Full Chilmark, MA market report ZIP 02575 market data
Listing Provided By

Listing Agent: Tina Miller

Listing Office: Compass

MLS® Number: 73495595

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