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 (105 Days)
$2,295,000 (USD)
4
BED
3.5
BATH
4,072
SQFT
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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 #:
73548377
Taxes
$5,655(2026)
Lot Size
1.94 acres
Type
Single-Family Home
Year Built
1970
Style
Cape, Contemporary
County
Barnstable County

Listed By

Janet Stuart, Coldwell Banker Realty
Source
MLS PIN
Last checked Oct 24 2026 at 8:35 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
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: 10
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.. 10/24/26 13:35

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