18 Windsor Drive Edgartown, MA ^$ 999,000

18 Windsor Drive

^$ 999,000

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18 Windsor Drive

Edgartown, MA, 02539

^$ 999,000

Bedrooms3 Baths2.0 Sq 1,294

Monthly Estimate*

^$ 6,151

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Single Family Home for sale in Edgartown, MA

for $999,000 with 3 bedrooms and 2 full baths. This 1,294 square foot home was built in 1981 on a lot size of 0.64.

Welcome to this light-filled Vineyard Cape brimming with potential, offering an open layout and abundant natural light. Vaulted ceilings enhance the spacious living and dining area, creating an airy setting for relaxing or entertaining. The kitchen flows seamlessly to an outdoor deck, ideal for summer gatherings and al fresco dining. Two bedrooms and a full bathroom with laundry complete the first floor. Upstairs, you’ll find a generous primary bedroom with abundant closet space, an additional full bathroom, and a cozy loft-style den overlooking the main living area. Centrally located just moments from the bike path, with easy access to Edgartown, nearby beaches, and all down-Island amenities, this property presents a wonderful opportunity to make it your own. With a 4-bedroom septic in place there is potential room for expansion. The property is being sold “AS IS”.

Single Family Active

Price

^$ 999,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 2,782

Style

Cape

Lot Size

0.64

Year Built

1981

Town/City

Edgartown

County/Region

Dukes

MLS | Web ID

73489567

List By

Stephanie Roache

Listing Agent

Donnelly + Co.

Broker

Affordability Calculator

$6,383

Per Month

Monthly Principal & Interest: $6,151
Monthly Property Taxes: $232
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 Edgartown, MA

Average List Price ^$4,733,308

Percent of Sale Price 374%

About Edgartown, MA

4,279 Population

13% Since 2002

^$75,439 Median Income

47.27 Median Age

18% 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
3/20/2026	$999,000		Listed Price

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18 Windsor Drive, Edgartown, MA, 02539 is a Single Family Home for sale at $999,000 with 1,294 sqft and a lot size of 0.64. 18 Windsor Drive has 3 bedrooms, 2.0 baths, and was built in 1981. The property's zip code is 02539 which is in Edgartown, 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 3/20/2026.

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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18 Windsor Drive

Single Family Home for sale in Edgartown, MA

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