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

Description

Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.

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

Listed By

Janet Stuart, Coldwell Banker Realty
Source
CCIMLS
Last checked Sep 16 2026 at 7:47 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 9/16/26 12:47. All properties are subject to prior sale, changes, or withdrawal.