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36 Smith Hollow Dr, 
Edgartown, MA 02539

$1,985,000


4

Beds


3

Baths


2,836

Sq Ft


Single Family

Active

Listed by

Katie Donahue & Rachel Serwa Group

Katie Donahue & Rachel Serwa Group

Sandpiper Realty, Inc.

508-627-3737

Last updated:

February 10, 2026, 11:45 AM

MLS#

73472940

Source:

MLSPIN

About This Home

36 Smith Hollow Dr

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.

Home Facts

Single Family

3 Baths

4 Bedrooms

Built in 1985

Price Summary

1,985,000

$699 per Sq. Ft.

MLS #:

73472940

Last Updated:

February 10, 2026, 11:45 AM


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

2,836 Sq. Ft.


Structure

Structure

Architectural Style:

Saltbox

Building Area:

2,836 Sq. Ft.

Year Built:

1985


Lot

Lot Size (Sq. Ft):

74,052


Finances & Disclosures

Finances

Price:

$1,985,000

Price per Sq. Ft:

$699 per Sq. Ft.

Source:MLSPIN
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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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.