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For Sale

55 Winterset Drive, Chatham MA 02633

Chatham, MA 02633

$2.29M
4 BD · 4 BA · 4,072 sf · 1.94 ac · Built 1970
The residence

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.

At a glance
Property type
Single Family Residence
Status
Active
Year built
1970
Lot size
1.94 acres
Living area
4,072 sf
MLS#
bc69cbd18adc62236bffac784234e122
Beds · Baths
4 · 4
Location

Chatham, MA.

Chatham sits at the elbow of Cape Cod, where Atlantic light, a working fishing fleet and a long Main Street of shopfronts set the pace. The lighthouse, the fish pier and the barrier beaches are the landmarks people navigate by.

Estimated Monthly Payment+
$11K/mo
Approximate · principal & interest only
Display Currency
$2.29M

Indicative conversion — settlement always in USD.

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Listing courtesy of Coldwell Banker Realty - Concord · MLSPIN

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Listings updated Oct 23, 2026

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