55 Winterset Drive Chatham, MA 02633
Listing Courtesy of: MLS LogoCCIMLS / Listed By: Janet Stuart, Coldwell Banker Realty

  55 Winterset Drive Chatham, MA 02633

Active (104 Days)
$2,295,000 (USD)
4
BED
4
BATH
4,072
SQFT

Description

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. garage, brand new Bosch heating system and newer roof. Close to Chatham Village, the Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

MLS #:
22603375
Taxes
$5,655(2026)
Lot Size
1.94 acres
Type
Single-Family Home
Year Built
1970
Style
Contemporary, Cape Cod
County
Barnstable County
Community
Great Hills

Listed By

Janet Stuart, Coldwell Banker Realty
Source
CCIMLS
Last checked Nov 3 2026 at 10:09 PM GMT+0000
Bathroom Details
  • Full Bathrooms: 3
  • Half Bathroom: 1
Interior Features
  • Recessed Lighting
  • Water Heater
  • Central Vacuum
  • Natural Gas
Subdivision
  • Great Hills
Lot Information
  • Corner Lot
Property Features
  • Fireplace: 4
Heating and Cooling
  • Natural Gas
  • Central Air
Basement Information
  • Full
  • Finished
Homeowners Association Information
  • Dues: $75/Annually
Flooring
  • Hardwood
Exterior Features
  • Roof: Asphalt
  • Roof: Shingle
Garage
  • Garage
Parking
  • Off Street
  • Paved
  • Total: 14
  • Garage Door Opener
  • Direct Access
Stories
  • 3

Listing Price History

Date
Event
Price
% Change
$ (+/-)
Sep 11, 2026
Price Changed
$2,295,000
-4%
-$95,000
Jul 12, 2026
Listed
$2,390,000
-
-
Location
   
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Disclaimer: The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. This site was last updated 11/3/26 14:09. All properties are subject to prior sale, changes, or withdrawal.