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 (10 Days)
$2,390,000 (USD)
4
BED
4
BATH
4,066
SQFT

Description

Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

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

Listed By

Janet Stuart, Coldwell Banker Realty
Source
CCIMLS
Last checked Jul 21 2026 at 7:02 PM GMT+0000
Bathroom Details
  • Full Bathrooms: 3
  • Half Bathroom: 1
Interior Features
  • Recessed Lighting
  • Laundry: Laundry Room
  • Water Heater
  • Central Vacuum
  • Breakfast Bar
  • Eat-In Kitchen
  • Kitchen Island
  • 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
  • Carpet
Exterior Features
  • Roof: Asphalt
  • Roof: Shingle
Garage
  • Garage
Parking
  • Off Street
  • Paved
  • Total: 14
  • Garage Door Opener
  • Direct Access
Stories
  • 3
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 7/21/26 12:02. All properties are subject to prior sale, changes, or withdrawal.