Skip to main contentSkip to navigation
1 / 51

Land with Home for Sale in South Dennis, Massachusetts

8 Winstons Path, South Dennis, MA 02660

$1,349,000
2.2 acres
Active sale
$51k drop
Est $7,278/mo

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!

3,079
Sq feet
3
Beds
2
Full baths
1
1/2 bath
1976
Built

Location

Street address
8 Winstons Path
Zip code
02660
Community
Dennis
School district
Dennis-Yarmouth
Elevation
17 feet
Coordinates
41.6792, -70.1535

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

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

DateEventPriceChangeSource
July 6, 2026Price drop$1,349,000$51,000 -3.6%CCIAOR
June 23, 2026New listing$1,400,000CCIAOR
Subscribe to listing updates

Payment calculator

This 2.21-acre property is located at 8 Winstons Path in South Dennis, MA 02660. The property is available for sale, priced at $1,349,000. It has a 3,079 square foot 3-bedroom, 2.5-bath house built in 1976.

Listed by Oceanside Realty Group, (774) 836-6953

Checked 2 hours agoUpdated Source

Report listing issue

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Contact listing agent Rules
By submitting, I agree to the terms of use and to be contacted by real estate professionals. Message and data rates may apply.
Contact