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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

Welcome to this exceptional Great Hill Estates retreat, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short stroll away. Elevated above a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out.A sought-after first-floor primary suite features an ensuite bath and laundry, providing convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent family room with vaulted beamed ceilings and a wood-burning fireplace. A separate living room with a gas fireplace opens to a wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs, two spacious bedrooms share a full bath, including one with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, second laundry area, and direct access to a stone patio with custom seating and a built-in gas fire pit. Additional highlights include central air conditioning, hardwood floors, a two-car attached garage, a brand-new Bosch heating system, and a newer roof. Just steps from the Cape Cod Rail Trail, tennis courts, and pickleball courts, this home is offered fully furnished and ready to enjoy.

$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 2:47 AM UTC, 11/3/2026

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