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

  55 Winterset Drive Chatham, MA 02633

Active (67 Days)
$2,295,000 (USD)
4
BED
3.5
BATH
4,072
SQFT
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Description

Set high on approximately 2 acres in Chatham’s Great Hill area, this sun-filled, wonderfully renovated home offers a rare combination of privacy, space, and 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. Deeded rights to Lovers Lake provide access for kayaking, canoeing, and swimming just steps away. 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, plus a primary bedroom with en-suite full bath, laundry, and ample closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level includes a bedroom, full bath, full laundry, and access to a stone patio with fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central air conditioning throughout, 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 #:
73548377
Taxes
$5,655(2026)
Lot Size
1.94 acres
Type
Single-Family Home
Year Built
1970
Style
Cape, Contemporary
County
Barnstable County
Community
Great Hill

Listed By

Janet Stuart, Coldwell Banker Realty
Source
MLS PIN
Last checked Sep 16 2026 at 9:59 AM GMT+0000
Bathroom Details
Interior Features
  • Range
  • Refrigerator
  • Dryer
  • Washer
  • Dishwasher
  • Microwave
  • Laundry: First Floor
  • Windows: Insulated Windows
  • Gas Water Heater
  • Oven
  • Washer/Dryer
  • Bathroom
  • Laundry: Gas Dryer Hookup
Kitchen
  • Flooring - Hardwood
  • Countertops - Stone/Granite/Solid
  • Deck - Exterior
  • Exterior Access
  • Kitchen Island
  • Recessed Lighting
  • Window(s) - Picture
  • Open Floorplan
Subdivision
  • Great Hill
Lot Information
  • Corner Lot
Property Features
  • Fireplace: 4
  • Fireplace: Living Room
  • Fireplace: Family Room
  • Fireplace: Bedroom
  • Foundation: Concrete Perimeter
Heating and Cooling
  • Natural Gas
  • Baseboard
  • Central Air
  • Ductless
Basement Information
  • Full
  • Garage Access
  • Finished
  • Walk-Out Access
  • Interior Entry
Homeowners Association Information
  • Dues: $75/Annually
Flooring
  • Tile
  • Hardwood
  • Carpet
Exterior Features
  • Roof: Shingle
Utility Information
  • Utilities: Water: Public, For Gas Range, Outdoor Gas Grill Hookup, For Gas Dryer
  • Sewer: Private Sewer
School Information
  • Elementary School: Chatham
  • Middle School: Chatham
  • High School: Monomoy
Garage
  • Attached Garage
Parking
  • Off Street
  • Paved Drive
  • Attached
  • Under
  • Garage Door Opener
  • Garage Faces Side
  • Total: 14
Living Area
  • 4,072 sqft

Listing Price History

Date
Event
Price
% Change
$ (+/-)
Sep 11, 2026
Price Changed
$2,295,000
-4%
-$95,000
Jul 11, 2026
Listed
$2,390,000
-
-
Location
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Disclaimer: The property listing data and information, or the Images, set forth herein wereprovided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. © 2026 MLS Property Information Network, Inc.. 9/16/26 02:59

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