205 South Rd Chilmark, MA ^$ 5,650,000

205 South Rd

^$ 5,650,000

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205 South Rd

Chilmark, MA, 02575

^$ 5,650,000

Bedrooms4 Baths4.1 Sq 5,402

Monthly Estimate*

^$ 34,788

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Single Family Home for sale in Chilmark, MA

for $5,650,000 with 4 bedrooms and 4 full baths, 1 half bath. This 5,402 square foot home was built in 1940 on a lot size of 5.99.

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.

Single Family Active

Price

^$ 5,650,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 13,900

Style

Cape

Lot Size

5.99

Year Built

1940

Town/City

Chilmark

County/Region

Dukes

MLS | Web ID

73495595

List By

Tina Miller

Listing Agent

Donnelly + Co.

Broker

Affordability Calculator

$35,946

Per Month

Monthly Principal & Interest: $34,788
Monthly Property Taxes: $1,158
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Chilmark, MA

Average List Price ^$3,032,222

Percent of Sale Price 46%

About Chilmark, MA

871 Population

5% Since 2002

^$91,667 Median Income

52.93 Median Age

17% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
4/3/2026	$5,650,000		Listed Price

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205 South Rd, Chilmark, MA, 02575 is a Single Family Home for sale at $5,650,000 with 5,402 sqft and a lot size of 5.99. 205 South Rd has 4 bedrooms, 4.1 baths, and was built in 1940. The property's zip code is 02575 which is in Chilmark, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 4/24/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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205 South Rd

Single Family Home for sale in Chilmark, MA

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