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4 Beds
5 Baths
6,162 sqft

$4,995,000

205 South Road, Chilmark MA, 02535

Price per sqft$810.61
Built in1940
Property size6,162 sqft
Property typeResidential

Overview

Pending

Listed Apr 3, 2026

Updated 2 weeks ago

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 square feet of gracious living space. The sunny, light-filled main house showcases an open kitchen and living area anchored by a striking central fireplace—ideal for both everyday year-round living and entertaining. An expanded primary suite wing includes a spacious primary bedroom, full bath, bright office, half bath, and dedicated laundry. A second-story space offers flexibility as an art studio, office, or media room. A classic three-season living room invites relaxed enjoyment of the surrounding landscape, including distant winter waterviews. Well-suited for compound living, the property is perfect for the equestrian and includes a guest house, horse barn, fenced pastureland, garage, and an old boat shed—providing exceptional flexibility for family, guests, and a wide range of outdoor pursuits. Deeded access to Chilmark Pond and South Shore Beach offers a rare opportunity to enjoy swimming, kayaking, and some of the Island’s most beautiful and unspoiled coastline. This property has a seven-bedroom septic, full solar, and abuts acres of conservation land. Ideally located in the heart of Chilmark, the property is just minutes from Alley’s Store, Lucy Vincent Beach, Chilmark Tavern, Beetlebung Farm, the Chilmark Store, and more—perfectly capturing the essence of the Chilmark lifestyle and the very best of Vineyard living.

$33,232/mo

Est. mortgage payment based on a $4,995,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
44028

Interior Features

Bedrooms
4
Bathrooms
5
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
5.99 Acres

Other Property Details

Taxes
$13,900
Tax Frequency
Annually

 

Courtesy of Donnelly + Co, Tina Miller

Based on information from LINK Martha's Vineyard as of 9/2/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

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Data last updated 3:50 AM UTC, 9/2/2026

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