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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 2 days 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
Available since
July 11, 2026

Interior Features

Bedrooms
4
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
1.94 Acres

Other Property Details

Taxes
$5,655
Tax Frequency
Annually
Garage
Yes

 

Courtesy of Janet Stuart

Based on information from DASH - Coldwell Banker (CB) as of 10/10/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

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Data last updated 9:12 AM UTC, 10/10/2026

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