8 Winstons Path South Dennis, MA $ 1,400,000
8 Winstons Path
$ 1,400,000
Recently Listed
Open House 6/28 11am - 1pm
Share Save

8 Winstons Path

South Dennis, MA, 02660
$ 1,400,000
Bedrooms3 Baths2.1 Sq 3,079

Monthly Estimate*

$ 8,840

8 Winstons Path, South Dennis, MA 02660 - Image 1
8 Winstons Path, South Dennis, MA 02660 - Image 2
8 Winstons Path, South Dennis, MA 02660 - Image 3
8 Winstons Path, South Dennis, MA 02660 - Image 4
8 Winstons Path, South Dennis, MA 02660 - Image 5
8 Winstons Path, South Dennis, MA 02660 - Image 6
8 Winstons Path, South Dennis, MA 02660 - Image 7
8 Winstons Path, South Dennis, MA 02660 - Image 8
8 Winstons Path, South Dennis, MA 02660 - Image 9
8 Winstons Path, South Dennis, MA 02660 - Image 10
8 Winstons Path, South Dennis, MA 02660 - Image 11
8 Winstons Path, South Dennis, MA 02660 - Image 12
8 Winstons Path, South Dennis, MA 02660 - Image 13
8 Winstons Path, South Dennis, MA 02660 - Image 14
8 Winstons Path, South Dennis, MA 02660 - Image 15
8 Winstons Path, South Dennis, MA 02660 - Image 16
8 Winstons Path, South Dennis, MA 02660 - Image 17
8 Winstons Path, South Dennis, MA 02660 - Image 18
8 Winstons Path, South Dennis, MA 02660 - Image 19
8 Winstons Path, South Dennis, MA 02660 - Image 20
8 Winstons Path, South Dennis, MA 02660 - Image 21
8 Winstons Path, South Dennis, MA 02660 - Image 22
8 Winstons Path, South Dennis, MA 02660 - Image 23
8 Winstons Path, South Dennis, MA 02660 - Image 24
8 Winstons Path, South Dennis, MA 02660 - Image 25
8 Winstons Path, South Dennis, MA 02660 - Image 26
8 Winstons Path, South Dennis, MA 02660 - Image 27
8 Winstons Path, South Dennis, MA 02660 - Image 28
8 Winstons Path, South Dennis, MA 02660 - Image 29
8 Winstons Path, South Dennis, MA 02660 - Image 30
8 Winstons Path, South Dennis, MA 02660 - Image 31
8 Winstons Path, South Dennis, MA 02660 - Image 32
8 Winstons Path, South Dennis, MA 02660 - Image 33
8 Winstons Path, South Dennis, MA 02660 - Image 34
8 Winstons Path, South Dennis, MA 02660 - Image 35
8 Winstons Path, South Dennis, MA 02660 - Image 36
8 Winstons Path, South Dennis, MA 02660 - Image 37
8 Winstons Path, South Dennis, MA 02660 - Image 38
8 Winstons Path, South Dennis, MA 02660 - Image 39
8 Winstons Path, South Dennis, MA 02660 - Image 40
8 Winstons Path, South Dennis, MA 02660 - Image 41
8 Winstons Path, South Dennis, MA 02660 - Image 42
8 Winstons Path, South Dennis, MA 02660 - Image 43
8 Winstons Path, South Dennis, MA 02660 - Image 44
8 Winstons Path, South Dennis, MA 02660 - Image 45
8 Winstons Path, South Dennis, MA 02660 - Image 46
8 Winstons Path, South Dennis, MA 02660 - Image 47
8 Winstons Path, South Dennis, MA 02660 - Image 48
8 Winstons Path, South Dennis, MA 02660 - Image 49
8 Winstons Path, South Dennis, MA 02660 - Image 50
8 Winstons Path, South Dennis, MA 02660 - Image 51

Single Family Home for sale in South Dennis, MA

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!

See more

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

Single Family Active

Price

$ 1,400,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 4,631

Style

Colonial

Lot Size

2.21

Year Built

1976

Town/City

South Dennis

County/Region

Barnstable

MLS | Web ID

22603047

Features
General
Sewer 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
See more
Interior
Basement 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
See more
Exterior
Total 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
See more
* Excluded Features
List By
Leo Doyle

Listing Agent

Oceanside Realty Group

Broker

leo@leosellscapecod.com

Email

Affordability Calculator

$9,226
Per Month
96%
4%
0%
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

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
4720468 Elementary School
4720469 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
6/23/2026$1,400,000 Listed Price

Map


See all

8 Winstons Path, South Dennis, MA, 02660 is a Single Family Home for sale at $1,400,000 with 3,079 sqft and a lot size of 2.21. 8 Winstons Path has 3 bedrooms, 2.1 baths, and was built in 1976. The property's zip code is 02660 which is in South Dennis, MA