
Residential Land with Home for Sale in Edgartown, Massachusetts
36 Smith Hollow Dr, Edgartown, MA 02539
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.
Location
- Street address
- 36 Smith Hollow Dr
- County
- Dukes County
- Elevation
- 39 feet
Directions
No drive-bys, owners in residence.
Property details
- Acreage
- 1.7 acres
- Zoning
- R60
- MLS #
- MVMLS 32500312
- Posted
Parcels
- 11-2-21
Details and features
Listing
- Type
- Residential Multi Family
Exterior
- Features
- Garden, Outdoor Shower, Private Yard
Structure
- Style
- Saltbox
- Stories
- 2
- Basement
- Finished, Full, Walk-Out Access
- Water
- Well
- Sewer
- Septic Tank
- Heating
- Baseboard, Hot Water, Propane
- Materials
- Shingle Siding
- Roof
- Shingle
Interior
- Room Count
- 11
- Rooms
- Basement, Bathroom x 3, Bedroom x 6
- Appliances
- Water Heater
Property utilities
| Category | Type | Status | Description |
|---|---|---|---|
| Gas | Propane | Connected | — |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Sept 12, 2025 | New listing | $1,985,000 | — | MVMLS |






































