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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 9h ago

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.

$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

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Data last updated 7:11 AM UTC, 10/6/2026

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