Raymond M. Hall, REALTOR® | Call | Text | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
This property was previously sold — it has since been re-listed. You are now viewing the current active listing.
$1,250,000
-10.7% from original list of $1,400,000 · October 12, 2026

8 Winstons Path, South Dennis, MA 02660

3 bedrooms 2 Full Baths 1 Half Bath 3,079 Sq Ft 2.21 acres 1 Car Garage
MLS# 22603047 · Residential / (Single Family Residence)
Listed: 06/23/26 (listing data as of 11/8/26 at 11:56 am)
  • Natural Light
  • Hardwood Floors
  • Primary Suite
  • Built-Ins
  • Finished Lower Level
  • Central A/C
  • 3 Fireplaces
  • Renovated 2018
  • 1-Car Garage

About This Property

One-of-a-Kind Dennis Retreat, Pond front Privacy on Over 2 Acres! Tucked away at the end of a quiet side street, this beautifully situated 3-bedroom, 2.5-bath Colonial offers a rare combination of privacy, space, and direct frontage on Fresh Pond. Surrounded by over 2 acres of natural beauty and abutting conservation land, this special property offers an ever-changing landscape to enjoy throughout the seasons. From lush summer greenery and vibrant fall foliage to peaceful winter pond views and the fresh colors of spring, there's something beautiful to appreciate year-round. Inside, the home is designed to embrace its spectacular setting. The spacious kitchen features cherry cabinetry, granite countertops, an impressive 8-foot island, and sliders to the deck. A dramatic wall of windows fills the living room with natural light and pond views, complemented by custom built-ins, hardwood floors, and a gas fireplace. Upstairs, the primary suite features cathedral ceilings, an updated private bath, and a walk-in closet, while two additional bedrooms and a full bath provide comfortable space for family and guests. The finished lower level offers a versatile bonus room with a wet bar and

Property Details

Property TypeResidential
(Single Family Residence)
StatusFor Sale
MLS Number22603047
Year Built1976
Annual Taxes$4,631 (2026)
Total Assessment$1,090,396
Square Footage3,079
Price/Sq Ft$406/sq ft
Lot Size2.21 acres
Total Rooms7
Bedrooms3
Full Baths2
Half Baths1
RenovatedYes
Year Renovated2018
Heat Source Oil
Add'l Heating Forced Hot Water
Cooling A/C Central Air
Garage Spaces1
Days on Market138
WaterfrontNo
Fireplaces3

Exterior Features

  • Private Yard
  • Underground Sprinkler System

Location

Sold History 8 Winstons Path last sold June 13, 2022 for $1,155,000
Listed At $1,135,000
Sale / List 101.8%
Days on Market 5
View full sold details

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Listing Courtesy of: Leo Doyle / Oceanside Realty Group

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than John C. Ricotta & Associates are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 11/08/2026. Neither the listing broker nor John C. Ricotta & Associates shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.