55 Winterset Drive Chatham, MA 02633
Listing Courtesy of: MLS LogoCCIMLS / Listed By: Janet Stuart, Coldwell Banker Realty

  55 Winterset Drive Chatham, MA 02633

Active (94 Days)
$2,295,000 (USD)
4
BED
4
BATH
4,066
SQFT

Description

Renovated and expanded Contemporary Cape at the end of a cul-de-sac on just under two acres allows for a unique amount of privacy while being less than a five minute drive to Chatham Village, Chatham Lighthouse, the Chatham Bars Inn and all that Chatham has to offer. As part of Great Hill Estates, this home has deeded rights to Lover's Lake for swimming, kayaking and canoeing. This home offers large open spaces perfect for entertaining and large gatherings. The first floor has a family room with vaulted beamed ceiling and wood burning fireplace open to a kitchen with large island and dining area, another large living room with gas fireplace open to a wraparound deck for grilling, dining and enjoying the views of nature looking out over the property. Enjoy a first floor primary with ensuite bathroom including laundry and a half bath. Upstairs are two more bedrooms, one as a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath. The lower level has a bedroom, a full bath, second laundry, and walk-out access to a stone patio with custom stone seating area and a built-in gas fire-pit. Features including central a/c, hardwood floors, two car attached garage, brand new Bosch heating system and newer roof. Just steps away from the Cape Cod Rail Trail Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

MLS #:
22603375
Taxes
$5,655(2026)
Lot Size
1.94 acres
Type
Single-Family Home
Year Built
1970
Style
Contemporary, Cape Cod
County
Barnstable County
Community
Great Hills

Listed By

Janet Stuart, Coldwell Banker Realty
Source
CCIMLS
Last checked Oct 24 2026 at 9:35 PM GMT+0000
Bathroom Details
  • Full Bathrooms: 3
  • Half Bathroom: 1
Interior Features
  • Recessed Lighting
  • Water Heater
  • Central Vacuum
  • Natural Gas
Subdivision
  • Great Hills
Lot Information
  • Corner Lot
Property Features
  • Fireplace: 4
Heating and Cooling
  • Natural Gas
  • Central Air
Basement Information
  • Full
  • Finished
Homeowners Association Information
  • Dues: $75/Annually
Flooring
  • Hardwood
  • Carpet
Exterior Features
  • Roof: Asphalt
  • Roof: Shingle
Garage
  • Garage
Parking
  • Off Street
  • Paved
  • Total: 14
  • Garage Door Opener
  • Direct Access
Stories
  • 3

Listing Price History

Date
Event
Price
% Change
$ (+/-)
Sep 11, 2026
Price Changed
$2,295,000
-4%
-$95,000
Jul 12, 2026
Listed
$2,390,000
-
-
Location
   
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Disclaimer: 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. This site was last updated 10/24/26 14:35. All properties are subject to prior sale, changes, or withdrawal.