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

Description

Wonderfully renovated and expanded Contemporary Cape set back at the end of a quiet cul-de-sac on just under two acres offering total privacy and nature at every turn. As part of Great Hill, this home includes deeded rights to Lover's Lake for swimming, kayaking, and canoeing just a short footpath away. Features include hardwood floors, lots of windows and french doors for loads of sunlight, open floor plan, vaulted ceilings and multiple decks all perfect for entertaining and large family gatherings. The first floor includes two great rooms each with vaulted beamed ceilings, one with a gas fireplace and one with a wood-burning fireplace, a renovated kitchen with a wall of windows at the kitchen sink overlooking the property, a large dining area, a half bath and a primary suite with ensuite renovated bathroom with large walk-in shower and laundry. Off the great room is a large wraparound deck with gas connection for the grill and room for full dining, lounging and taking in the professionally landscaped grounds, sprawling flower beds and quaint stone walls. Off the other great room and connecting with the kitchen is another deck overlooking the property with a perfect spot for morning coffee, reading and relaxing. On the second floor is a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath with shower and separate spa tub. The lower level has a bedroom with sitting area and full window, a full bath, another laundry, and walk-out access to a stone patio with custom stone wraparound seating and a built-in gas fire-pit. Enjoy brand new Bosch heating system, central a/c, central vac, attached 2 car garage, gas connection and town water. Key location with easy access to Route 6 for commuting off cape and the outer cape areas.yet a 5-minute drive to Chatham Village, Chatham Light, Lighthouse Beach, Chatham Bars Inn, Seaside Links Golf Course, and Hardings Beach. Steps to tennis courts, pickleball courts and the Chatham Scenic Bike Loop connecting to the Cape Cod Rail Trail bike path. House comes 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 20 2026 at 2:26 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
   
Calculate drive times to this property
 
Powered by INRIX® Drive Time

Powered by Walk Score®

Estimated Monthly Mortgage Payment

*Based on Fixed Interest Rate withe a 30 year term, principal and interest only

Listing price
Down payment
%
Interest rate
%
Mortgage calculator estimates are provided by Coldwell Banker Real Estate LLC and are intended for information use only. Your payments may be higher or lower and all loans are subject to credit approval.
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 10/20/26 07:26. All properties are subject to prior sale, changes, or withdrawal.