36 Smith Hollow Dr

Taxes: $5,249 (2026)

About this home

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.

Property details

Sewer

On-Site

Style

Other (See Remarks)

Water

Private Water

Cooling

Window AC, Wall AC

Heating

Electric Baseboard, Hot Air Gravity

Type

Detached

Road type

Private

Construction

Post & Beam

Roof

Aluminum

Garage

Detached, Storage, Insulated

Lot

Cleared, Gentle Slope, Level

Parking

1-10 Spaces

Basement

Full, Partially Finished, Walk Out, Interior Access

Exterior

Deck - Wood, Storage Shed, Guest House, Outdoor Shower