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Properties

  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
  • 36 Smith Hollow Dr, Edgartown, Massachusetts, 4 Bedrooms Bedrooms, 11 Rooms Rooms,2.5 BathroomsBathrooms,Residential,For Sale,Smith Hollow Dr,73472940
Property Description

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.

Features
Heating System:
Baseboard, Natural Gas
Cooling System:
Window Unit(s), Wall Unit(s)
Basement:
Full, Partially Finished, Walk-out Access, Interior Entry
Parking:
Storage, Off Street, Detached, Insulated
Construction:
Post & Beam
Exterior Unit Features:
Outdoor Shower, Deck - Wood, Guest House, Storage
Sewer:
Private Sewer
Style:
Saltbox
Water:
Private
Garage Parking:
2
Lead Paint:
No
Additional Information
Area:
Edgartown
Market Time:
143
Parking Spaces:
8
Tax Year:
2026
Status:
Active
Price Per Sqft:
$700
Zoning:
R60
Orig Price:
$1,985,000
Waterfront:
No
MlsStatus:
Active
Address Map
City:
Edgartown
State:
MA
County:
Dukes
Postal Code:
02539
Longitude:
W71° 26' 10.5''
Latitude:
N41° 24' 14.2''
  • Google Map

Residential

36 Smith Hollow Dr, Edgartown, Massachusetts

4 Bedrooms
2.5 Total Bathrooms
2,836 Sqft
$1,985,000
Listing ID #73472940
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$1,985,000
Bedrooms :
4
Rooms :
11
Total Bathrooms :
2.5
Full Bathrooms :
2
Half Bathrooms :
1
Square Footage :
2,836 Sqft
Year Built :
1985
Lot Area :
1.70 Acre
Listing ID :
73472940
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

The property listing data and information 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 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 set forth herein.

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