
Land with Home for Sale in South Dennis, Massachusetts
8 Winstons Path, South Dennis, MA 02660
A One of a kind Dennis location. Pond-Front Privacy on 2+ Acres! Tucked away on a private, wooded lot sitting on Fresh Pond, this 3-bedroom, 2.5-bath Colonial offers a rare combination of space, serenity, and water views. Tucked at the end of a quiet little side street, you'll enjoy over 2 acres of privacy with direct pond frontage--perfect for kayaking, fishing, or simply relaxing in a peaceful natural setting. Inside, the home is designed to capture the pond views throughout. Highlights include a huge kitchen with cherry cabinetry, granite counters, and an 8-foot island, with sliders to the deck. The living room features a dramatic wall of windows, custom built-ins, wood floors, and a gas fireplace. Upstairs, the primary suite offers cathedral ceilings, updated bath, and a walk-in closet. Two guest bedrooms and a full bath complete the second level. The lower-level bonus room adds great space for family and friends with a wet bar and direct access to the patio and pond. This hidden retreat abutting conservation land provides unmatched privacy but is still close to everything great about owning a home in Dennis!
Location
- Street address
- 8 Winstons Path
- County
- Barnstable County
- Zip code
- 02660
- Community
- Dennis
- School district
- Dennis-Yarmouth
- Elevation
- 17 feet
Directions
Old Main Street to Winston's Path, private road. Drive past barn on your right, continue down to the end of the road to circular drive at #8.
Property details
- Acreage
- 2.21 acres
- Zoning
- R-40
- MLS #
- CCIAOR 22603047
- Posted
Property taxes
- 2026
- $4,631
Parcels
- DENN M:000108 P:017-000
Open houses
| Date | Begins | Ends | Appt needed | Remarks |
|---|---|---|---|---|
| June 27, 2026 | 11:00 AM | 1:00 PM | No | 1st Open House |
| June 28, 2026 | 11:00 AM | 1:00 PM | No | — |
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
Exterior
- Parking Spaces
- 8
- Features
- Private Yard, Underground Sprinkler System
Structure
- Stories
- 2
- Basement
- Finished, Walk-Out Access
- Water
- Public
- Heating
- Oil
- Cooling
- Central Air
- Materials
- Clapboard, Shingle Siding
- Roof
- Asphalt
Interior
- Room Count
- 7
- Rooms
- Basement, Bathroom x 3, Bedroom x 3
- Flooring
- Carpet, Hardwood, Tile
- Fireplaces
- Yes
- Appliances
- Water Heater
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| June 23, 2026 | New listing | $1,400,000 | — | CCIAOR |


















































