36 Smith Hollow Dr, Edgartown, MA 02539

• 5 beds |
• 3 baths |
• 2,836 sqft

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 one-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.

Listing Status:

Pending

Date Added:

September 13, 2025

Data Last Updated:

April 5, 2026 at 12:07AM

Listing Office:

Sandpiper Realty, Inc. : 508-627-3737

Listing Agent:

Katie Donahue & Rachel Serwa Group : 413-559-0053

MLS ID:

73472940

Interior

• Basement: FullPartially FinishedWalk-Out AccessInterior Entry
• A/C: Window Unit(s)Wall Unit(s)
• Heating: BaseboardNatural Gas
• Fireplace: Fireplaces: 0

Exterior

• General: Deck - WoodStorageGuest HouseOutdoor ShowerGuest House
• Style: Saltbox
• Parking: DetachedStorageInsulatedOff StreetParking spaces: 8

Construction

• Roofing: Shingle
• General: Post & BeamConcrete Perimeter

Location

• Road/Access: Private Road
• Originating MLS: MLS Property Information Network
• County: Dukes

Lot

• Zoning: R60M:0011 B:0002 L:213768520

Utilities

• Water: Private
• Sewer: Private Sewer

Financial

• Source: MLS Property Information Network