205 South Road

Chilmark MA 02535

5402 sq. ft.

260924 sq. ft.

Single-Family

Last sold for $4,550,000

Tina Miller, last sold this property on 06 October 2026 after 185 days on market.

Overview

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.

Features

4 bedrooms

5 bathrooms

11 carspaces

8 open car spaces

3 garage spaces

5402 sq. ft. floor area

260924 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Chilmark over the last 12 months, the estimated median property value of 205 South Road is $5.25m.

Median value

$5.25m

Estimated value range

$2.1m - $10.5m

Median days on market

Estimated value trend

136%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Chilmark. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 205 South Road

2026

Sold

$4,550,000

06 Oct 2026 by Tina Miller, of Donnelly + Co.

Happy sellers in Chilmark

We have insufficient information to provide an overview of customer satisfaction for Chilmark. Viewing the agent profiles, reviews and sales for Chilmark can provide insights for this location.