Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,400,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,079 Sq. Ft.
  • 2.21 Acres
  • Updated 12 hours ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 6/27 11:00 AM - 1:00 PM

8 Winstons Path,Dennis, MA 02660

8 Winstons PathDennisMA02660

Get directions

View more dates

Join us at 8 Winstons Path on:

  • Open House: 11:00 AM - 1:00 PM

    Sunday 6/28 11:00 AM - 1:00 PM

    8 Winstons Path,Dennis, MA 02660
    8 Winstons PathDennisMA02660
See This Home
Save This Home
See This Home
Save This Home
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!

Full Property Details for 8 Winstons Path

General

  • Price: $1,400,000
  • Taxes: $4,631 (2026)
  • Status: Active
  • Type: Single Family
  • Source: CCI
  • MLS ID: 22603047
  • Updated: Today (6/23/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 7
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Electric Water Heater
  • Flooring: Hardwood, Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Parking

  • Garage: Yes
  • Total Spaces: 8

Location

  • County: Barnstable
  • Driving 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.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water

Utilities

  • Sewer: Private Sewer

Structural Information

  • Architectural Style: Colonial
  • Construction: Clapboard, Shingle Siding
  • Exterior Const.: Clapboard, Shingle Siding
  • Basement Desc.: Finished
  • Roof: Asphalt
  • Stories/Levels: 2
  • Square Feet: 3,079
  • Year Built: 1976
  • Property Condition: Updated/Remodeled, Actual

Lot Features

  • Lot Size (Acres): 2.21
  • Lot Size (Sq. Ft.): 96,268
  • Lot Size Source: Assessor
  • Frontage: Private Road
  • Zoning: R-40

Financial Considerations

  • Price Per Sq. Ft.: $454
  • Assessment Amount: $2,159,200
  • Land Assmt: $290,700
  • Tax Amount: $4,631
  • Tax Year: 2026

Disclosures and Reports

  • Special Conditions: None
  • Property ID: DENN M:000108 P:017000

Listed by Oceanside Realty Group, Leo Doyle

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 8 Winstons Path —

  • Leo Doyle

    Oceanside Realty Group

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 8 Winstons Path

School District:Dennis-Yarmouth School District
NameGradesDistance
Ezra H Baker
810 Route 28, Dennis, MA 02670
PK-30.7 mi
Dennis-Yarmouth Intermediate School
286 Station Avenue, Yarmouth, MA 02664
4-52.3 mi
Dennis-Yarmouth Regional High School
210 Station Avenue, Yarmouth, MA 02664
9-122.1 mi
Dennis-Yarmouth Middle School
286 Station Avenue, Yarmouth, MA 02664
6-82.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 8 Winstons Path Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/23/2026
Listed
$1,400,000
21.21%
MLS
6/13/2022
Sold
$1,155,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 8 Winstons Path

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,351
-3%
$1,004,900
-1%
2024
$4,475
4%
$1,019,300
10%
2023
$4,317
5%
$924,500
26%
2022
$4,099
-1%
$732,000
7%
2021
$4,130
6%
$684,900
7%
2020
$3,891
1%
$637,900
2%
2019
$3,847
7%
$623,500
10%
2018
$3,581
3%
$564,900
—
2017
$3,474
-2%
$564,900
4%
2016
$3,537
2%
$541,600
—
2015
$3,466
13%
$541,600
13%
2014
$3,056
—
$481,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 8 Winstons Path

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Oceanside Realty Group, Leo Doyle

Similar Properties near 8 Winstons Path

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

13 Academy Hill Ln, Dennis, MA 02660 - Photo 1 Price Reduced
-$75,600 (-4.8%)
$1,499,900

13 Academy Hill Ln  Dennis, MA 02660

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,310
    Sq. Ft.
19 Aunt Debbys Rd, Dennis, MA 02638 - Photo 1
$1,299,000

19 Aunt Debbys Rd  Dennis, MA 02638

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,506
    Sq. Ft.
19 Aunt Debbys Rd, Dennis, MA 02639 - Photo 1 Just Listed
$1,299,000

19 Aunt Debbys Rd  Dennis, MA 02639

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,506
    Sq. Ft.
29 Bass River Rd, Yarmouth, MA 02664 - Photo 1
$1,395,000

29 Bass River Rd  Yarmouth, MA 02664

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 2,328
    Sq. Ft.

Just Listed near 8 Winstons Path

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

12 Walnut St, Yarmouth, MA 02675 - Photo 1 Just Listed
$699,000

12 Walnut St  Yarmouth, MA 02675

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,920
    Sq. Ft.
Listed by Lea Pongonis (781) 706-3425
510 North Dennis, Yarmouth, MA 02675 - Photo 1 Just Listed
$789,000

510 North Dennis  Yarmouth, MA 02675

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,790
    Sq. Ft.
9 Deerfield Rd, Yarmouth, MA 02673 - Photo 1 Just Listed
$615,000
Open House

9 Deerfield Rd  Yarmouth, MA 02673

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,040
    Sq. Ft.
106 White Rock Rd, Yarmouth, MA 02675 - Photo 1 Just Listed
$699,000
Open House

106 White Rock Rd  Yarmouth, MA 02675

  • Single Family
  • Active
  • Updated 1 hour ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,648
    Sq. Ft.

Price Reduced near 8 Winstons Path

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

27 Angus Ave, Yarmouth, MA 02664 - Photo 1 Price Reduced
-$9,000 (-3.53%)
$245,900

27 Angus Ave  Yarmouth, MA 02664

  • Lots/Land
  • Active
  • Updated 5 days ago
  • 0.61
    Acres
216 Cranberry Ln, Yarmouth, MA 02664 - Photo 1 Price Reduced
-$16,000 (-2.37%)
$659,000

216 Cranberry Ln  Yarmouth, MA 02664

  • Single Family
  • Active
  • Updated 5 hours ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,012
    Sq. Ft.
17 Angus Ave, Yarmouth, MA 02664 - Photo 1 Price Reduced
-$10,000 (-4.45%)
$214,900

17 Angus Ave  Yarmouth, MA 02664

  • Lots/Land
  • Active
  • Updated 5 days ago
  • 0.92
    Acres
46 Route 6A, Yarmouth, MA 02675 - Photo 1 Price Reduced
-$130,000 (-7.12%)
$1,695,000

46 Route 6A  Yarmouth, MA 02675

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,717
    Sq. Ft.

Recent Sales near 8 Winstons Path

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

23 Farm Ln, Dennis, MA 02660 - Photo 1 Sold
$1,200,000

23 Farm Ln  Dennis, MA 02660

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,262
    Sq. Ft.
3 Pinefield Ln, Dennis, MA 02660 - Photo 1 Sold
$1,500,000

3 Pinefield Ln  Dennis, MA 02660

  • Single Family
  • Closed
  • 4
    Beds
  • 5
    Total Baths
  • 2,660
    Sq. Ft.
7 Vinland Dr, Dennis, MA 02660 - Photo 1 Sold
$1,400,000

7 Vinland Dr  Dennis, MA 02660

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,735
    Sq. Ft.
86 Greenland Cir, Dennis, MA 02641 - Photo 1 Sold
$1,555,375

86 Greenland Cir  Dennis, MA 02641

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 3,202
    Sq. Ft.

8 Winstons Path, Dennis, MA 02660 (MLS# 22603047) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 8 Winstons Path is currently listed for $1,400,000 and was received on June 23, 2026. Want to learn more about 8 Winstons Path? Do you have questions about finding other Single Family real estate for sale in South Dennis? You can browse all South Dennis real estate or contact a Coldwell Banker agent to request more information.

Tour this property