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

Set high on 1.8 acres at the end of a quiet cul-de-sac, this expanded renovated contemporary Cape offers privacy, beautiful natural surroundings, and an exceptional setting for large family gatherings and entertaining. Located in one of Chatham’s most sought-after areas, the home offers the best of both worlds—a peaceful, private setting with convenient access to Chatham Village, the bike path, and some of Chatham’s most beautiful beaches. As a member of the Great Hill Estates Association, the property also includes rights to Lovers Lake. Treetop views, abundant windows, and multiple decks bring the beauty of the setting into the home. The expansive outdoor living spaces are designed for entertaining, with a large deck, additional seating areas, a gas line for grilling, and a stone patio with a gas fire pit and built-in stone seating. A fenced area in the backyard provides a convenient space for a dog. The first floor features two spacious great rooms, each with dramatic open-beamed ceilings and fireplaces, along with a large kitchen with granite countertops, island seating, and an open dining area. A half bath and first-floor primary suite with an en-suite full bath and laundry complete the main level. Upstairs, another bedroom offers its own fireplace and sitting area, along with an additional bedroom and full bath. The lower level provides a fourth bedroom, full bath, laundry, and walkout access to the patio. With generous living spaces indoors and out, this home is perfectly suited for entertaining, holidays, and gathering with family and friends. A new Bosch heating system adds peace of mind. Enjoy the privacy and natural beauty of this special property while being just minutes from all that makes Chatham such a sought-after destination.

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 Oct 4 2026 at 1:07 PM 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.. 10/4/26 06:07

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