$4,995,000
Unlock Price Rating!

205 South RD, Chilmark, MA 02575

 Contact
4 Beds
5 Baths
5,402 Sq Ft

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 fireplaceideal 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.

Listing By: mamlspin Realty.com
  • MLS# 73495595
  • Date Listed04/03/2026
  • Days on Realty 150 Days
  • Bedrooms 4
  • Bathrooms 4 Full baths, 1 Half baths
  • Lot Size 5.99 acres (260,924 sq. ft)
  • Sewer Inspection Required for Sale
  • Property Type Single Family
  • County Dukes
  • Year Built 1940
  • Water Private
  • Square Feet 5,402 sq. ft
  • Price Per Sq. Ft $924.66

Interior Features

  • Appliances Water Heater
  • Cooling Heat Pump
  • Heating Radiant, Heat Pump

Exterior / Lot Features

  • Roof -
  • Lot Size Acres 5.99
  • Lot Size SQFT 260,924.00
  • Lot Features Wooded, Cleared, Gentle Sloping

Directions

Heading Up-Island, 205 South Rd will be on your right. PROPERTY IS OCCUPIED. Please NO drive bys.

Financial Considerations

  • Tax Amount $13,900
  • Terms Cash, Conventional, FHA, VA Loan

Schools near 02575

Explore the local neighborhood highlights and top-rated schools near 02575 in Chilmark, MA.

Nearby Schools

Source: School Digger

West Tisbury Elementary School

Public • PK - 8 • Serves this home

5.02 mi

Distance

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for 02575

Discover key demographics, population statistics, and environmental insights for the Chilmark, MA area.

Population & Environment

Source: Sperling's Best Places

Walkability in MA / 02575

Source: Walk Score

4/100

Car-Dependent

Walk Score ®

0/100

Minimal Transit

Transit Score ®

28/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 4/100, Transit Score: 0/100, Bike Score: 22/100.

Property Change History

List Price decreased from $5,350,000 to $4,995,000
Price Per Square Foot decreased from $990.37 to $924.66
Property Heating updated
Heat Pump, Radiant → Radiant, Heat Pump
List Price decreased from $5,650,000 to $5,350,000
Price Per Square Foot decreased from $1,045.91 to $990.37
Property Heating updated
Heat Pump, Central → Heat Pump, Radiant
Agent added 1 new photo to the listing
41 → 42 photos
Property description updated with new details
Agent added 1 new photo to the listing
40 → 41 photos

Points of Interest near 205 South Rd, Chilmark, MA 02575

Frequently Asked Questions for 205 South Rd

Source: Realty.com

205 South Rd, Chilmark, MA 02575 in Chilmark, MA 02575 is a single family listed at $4,995,000. Highlights include 4 bedrooms, 5 bathrooms, 5,402 sq. ft., built in 1940, 5.99 acre lot, $925 per sq. ft.. Realty.com has 42 photos, sales history, school insights, and mortgage tools for this listing.

Realty.com has 42 photos of 205 South Rd.

Our records indicate that 205 South Rd was built in 1940.

The full address for this home is 205 South Rd, Chilmark, MA 02575.

205 South Rd has been listed on Realty.com since Fri April 03, 2026

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 4/100, Transit Score: 0/100, Bike Score: 22/100.

There are 1 schools assigned to this home. Check out the schools near 205 South Rd. West Tisbury Elementary School (Grades: PK - 8)

Listing provided courtesy of: Donnelly + Co. (tel: 508-627-1022)
Listing agent: Tina Miller (tel: 508-561-0042) (#CN236935)

This content last refreshed on 2026-08-31 16:07:04. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.