Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
4 Beds
4 Baths
4,072 sqft

$2,295,000

55 Winterset Drive, Chatham MA, 02633

Price per sqft$563.61
Built in1970
Property size4,072 sqft
Property typeResidential

Overview

Active

Listed Jul 11, 2026

Updated 2h ago

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.

$15,269/mo

Est. mortgage payment based on a $2,295,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
73548377

Interior Features

Bedrooms
4
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.94 Acres

Other Property Details

Taxes
$5,655
Tax Frequency
Annually
Association Fee Frequency
Yearly
Garage
Yes
55+/Senior Community
No

This listing is provided by Janet Stuart with Coldwell Banker Realty - Concord

The property listing data and images displayed herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors, and public records, and compiled by MLS Property Information Network, Inc. This information is intended solely for the personal, non-commercial use of consumers who have a genuine interest in purchasing or leasing listed properties. It may not be used for any purpose other than to identify prospective properties of interest.

MLS Property Information Network, Inc. and its subscribers make no representations or warranties regarding the accuracy of the listing data or images presented.

©2026 MLS Property Information Network, Inc. All rights reserved.

Data last updated 4:26 PM UTC, 10/24/2026

Powered by Luxury Presence