Recently Listed Open House 6/28 11am - 1pm
8 Winstons Path
South Dennis, MA, 02660 $ 1,400,000
Bedrooms3 Baths2.1 Sq 3,079 Monthly Estimate*
$ 8,840
for $1,400,000 with 3 bedrooms and 2 full baths, 1 half bath. This 3,079 square foot home was built in 1976 on a lot size of 2.21.
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!
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Open House
6/28/2026 11:00 AM - 1:00 PM
8 Winstons Path South Dennis, MA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesGeneralSewer Private Sewer
Heating Hot Water
Cooling Central Air
Roof Asphalt
Appliances Electric Water Heater
Zoning R-40
Garage Spaces 1
Architectural Style Colonial
Construction Materials Clapboard Shingle Siding
Year Built 1976
Stories Count 2
Township Dennis
Property Subtype Single Family Residence
Tax Year 2026
County Barnstable
New Construction false
Property Type Residential
HOA false
Garage Y/N true
Total Rooms 7
Full Baths 2
Status Active
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.
City South Dennis
High School District Dennis-Yarmouth
Lot Size Units Acres
Lot Size Square Feet 96268
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 4631
Showing Instructions NO DRIVE-BYS PLEASE PRIVATE ROAD. Showings by Appointment Only. Call or text Leo at 508-280-7951.
Home Warranty Y/N false
Property Condition Updated/Remodeled Actual
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Dennis-Yarmouth
Elementary School District Dennis-Yarmouth
Tax Assessed Value 2159200
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InteriorBasement Finished
Flooring Hardwood Carpet Tile
Total Fireplaces 3
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Total Bedrooms 3
Below Grade Finished Area Unit Type Square Feet
Total Baths 3
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ExteriorTotal Parking 8
Lot Size Area 2.21
Foundation Details Poured
Building Area Total 3079
Lot Size Acres 2.21
Lot Size Source Assessor
Waterfront Y/N false
Road Frontage Type Private Road
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* Excluded FeaturesList ByOceanside Realty GroupBroker
leo@leosellscapecod.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $8,840
- Monthly Property Taxes
- $386
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in South Dennis, MA
Average List Price $1,294,596
Percent of Sale Price 8%
About South Dennis, MA 6,324 Population
-3% Since 2002
$ 54,881 Median Income
55.63 Median Age
13% Households with Children
Trends Information provided by ATTOM Data Solutions.
4720468 Elementary School
4720469 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 6/23/2026 | $1,400,000 | | Listed Price |