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Active Under Contract

205 South Rd

Chilmark, MA 02575

Offered at$4,995,000

Residential · Active Under Contract · MLS #73495595
Listing Courtesy of Compass | Tina Miller

4Bedrooms
5Bathrooms
5,402Square feet
1940Year built

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MLS PIN data

About this home

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.

Property information

Details at a glance

Interior

Rooms
9
Heating
Radiant, Heat Pump
Cooling
Heat Pump
Fireplaces
1

Building

Style
Single Family Residence
Year built
1940
Garage
3
Parking
11
Foundation
Concrete Perimeter

Land & utilities

Lot size
5.99 acres
Water
Private
Sewer
Inspection Required for Sale
Zoning
RES

Financial

Annual taxes
$13,900
Assessment year
2025

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$7,934,114

Estimated range $6,581,578$9,286,649

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationabove average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Chilmark

MetricThis propertyChilmark
List price$4,995,000$1,925,000159% above local
Price / sq ft$925$1,28628% below local
Days on market15310546% above local
Explore homes in Chilmark

Active neighborhood listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.

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Common questions

About 205 South Rd

Can I schedule a private showing?

Yes. Request a tour of 205 South Rd and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.