49 Gosnolds Way Chilmark, MA ^$ 5,200,000

49 Gosnolds Way

^$ 5,200,000

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49 Gosnolds Way

Chilmark, MA, 02535

^$ 5,200,000

Bedrooms5 Baths3.1 Sq 4,044

Monthly Estimate*

^$ 32,017

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Single Family Home for sale in Chilmark, MA

for $5,200,000 with 5 bedrooms and 3 full baths, 1 half bath. This 4,044 square foot home was built in 2003 on a lot size of 9.8.

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

Single Family Active

Price

^$ 5,200,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 8,293

Style

Contemporary

Lot Size

9.8

Year Built

2003

Town/City

Chilmark

County/Region

Dukes

MLS | Web ID

73534187

List By

Bonnie Pierce

Listing Agent

Wallace & Co. Sotheby's International Realty

Broker

Affordability Calculator

$32,708

Per Month

Monthly Principal & Interest: $32,017
Monthly Property Taxes: $691
Monthly Home Insurance: --

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Yearly Home Insurance

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 ^$6,726,250

Percent of Sale Price 29%

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.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
6/11/2026	$5,200,000		Listed Price

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49 Gosnolds Way, Chilmark, MA, 02535 is a Single Family Home for sale at $5,200,000 with 4,044 sqft and a lot size of 9.8. 49 Gosnolds Way has 5 bedrooms, 3.1 baths, and was built in 2003. 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 6/11/2026.

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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49 Gosnolds Way

Single Family Home for sale in Chilmark, MA

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