Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 2 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 3 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 4 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 5 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 6 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 7 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 8 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 9 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 10 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 11 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 12 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 13 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 14 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 15 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 16 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 17 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 18 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 19 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 20 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 21 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 22 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 23 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 24 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 25 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 26 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 27 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 28 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 29 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 30 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 31 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 32 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 33 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 34 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 35 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 36 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 37 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 38 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 39 of 40
Single Family Residence at 8 Winstons Path, Dennis MA 02660, Dennis, photo 40 of 40
40 photos

$1,349,000

8 Winstons Path, Dennis MA 02660
Dennis, MA 02660
Listed by Leo Doyle
Bedrooms
3
Bathrooms
2.1
Living area
3,079 sqft
Year built
1976

About this home

A One of a kind Dennis location. Pond-Front Privacy on 2+ Acres! Tucked away on a private lot sitting on Fresh Pond, this 3-bedroom, 2.5-bath Colonial offers a rare combination of space, serenity, and water views. Sitting at the end of a quiet side street, with 2 acres of privacy and 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 an 8-foot island and 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, an 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 oasis abuts conservation but is still close to everything great in Dennis!

Highlights

WaterfrontFireplace

Property details

MLS #
73541191
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
64
On market date
June 24, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
1
Parking spaces
6
Lot size
2.21 acres
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Ezra H Baker Innovation School
0.75 mi away · Grades -1-3
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
305
Student:teacher ratio
8.2:1
District
Dennis-Yarmouth
Middle
Nathaniel H. Wixon School
2.47 mi away · Grades 4-7
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
442
Student:teacher ratio
10.5:1
District
Dennis-Yarmouth
High
Dennis-Yarmouth Regional High
2.11 mi away · Grades 8-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
900
Student:teacher ratio
11.1:1
District
Dennis-Yarmouth

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$8,274/mo
$269,800 down
$1,079,200 loan
Principal & interest$7,000
Property tax (est.)$1,124
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated July 10, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.