36 Smith Hollow Dr Edgartown, MA ^$ 1,985,000

36 Smith Hollow Dr

^$ 1,985,000

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36 Smith Hollow Dr

Edgartown, MA, 02539

^$ 1,985,000

Bedrooms4 Baths2.1 Sq 2,836

Monthly Estimate*

^$ 12,222

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Single Family Home for sale in Edgartown, MA

for $1,985,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,836 square foot home was built in 1985 on a lot size of 1.7.

Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate two-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and independence, complete with its own driveway and parking. The detached garage, with a loft above, adds even more versatility—ideal for storage or future finished space. Situated on one of the largest parcels in the Smith Hollow Association, the property enjoys a tranquil, park-like setting. With direct access to the bike path at the end of the road, you're just minutes from Edgartown and all down-island amenities. More than just a house—this is a place to call home.

Single Family Active

Price

^$ 1,985,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 5,249

Style

Saltbox

Lot Size

1.7

Year Built

1985

Town/City

Edgartown

County/Region

Dukes

MLS | Web ID

73472940

List By

Katie Donahue & Rachel Serwa Group

Listing Agent

Sandpiper Realty, Inc.

Broker

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$12,659

Per Month

Monthly Principal & Interest: $12,222
Monthly Property Taxes: $437
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 Edgartown, MA

Average List Price ^$3,003,636

Percent of Sale Price 51%

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.

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Pricing History

Date	Price	Price Change	Description
1/30/2026	$1,985,000		Listed Price

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36 Smith Hollow Dr, Edgartown, MA, 02539 is a Single Family Home for sale at $1,985,000 with 2,836 sqft and a lot size of 1.7. 36 Smith Hollow Dr has 4 bedrooms, 2.1 baths, and was built in 1985. 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 1/31/2026.

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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36 Smith Hollow Dr

Single Family Home for sale in Edgartown, MA

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