308 South Road Chilmark, MA ^$ 7,350,000

308 South Road

^$ 7,350,000

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308 South Road

Chilmark, MA, 02535

^$ 7,350,000

Bedrooms4 Baths4.1 Sq 3,490

Monthly Estimate*

^$ 45,255

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Single Family Home for sale in Chilmark, MA

for $7,350,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,490 square foot home was built in 1999.

Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access. The beautifully manicured path, leads from the house to the dock, where you can launch across the pond to your own private South Shore beach lot, included in this sale. Of course the new owner also has access to iconic Lucy Vincent and Squibnocket beaches. The property is surrounded by over seven acres of abutting conservation land. The grounds are meticulously designed, with mature landscaping and gardens that feel both timeless and intentional. This is more than a residence. It's the key to embracing the Chilmark lifestyle defined by privacy, water access, and understated elegance.

Single Family Active

Price

^$ 7,350,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 18,310

Style

Cape

Year Built

1999

Town/City

Chilmark

County/Region

Dukes

MLS | Web ID

73478310

List By

Rose Ryley

Listing Agent

Wallace & Co. Sotheby's International Realty

Broker

Affordability Calculator

$46,781

Per Month

Monthly Principal & Interest: $45,255
Monthly Property Taxes: $1,526
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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Trends

Single family listings in Chilmark, MA

Average List Price ^$2,705,000

Percent of Sale Price 63%

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
2/18/2026	$7,350,000		Listed Price

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308 South Road, Chilmark, MA, 02535 is a Single Family Home for sale at $7,350,000 with 3,490 sqft. 308 South Road has 4 bedrooms, 4.1 baths, and was built in 1999. The property's zip code is 02535 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 2/20/2026.

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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308 South Road

Single Family Home for sale in Chilmark, MA

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