$2,295,000
4 Bed
3 Bath
4,066 Sqft Building
84,506 Sqft Lot

55 Winterset Drive, Chatham, Massachusetts 02633

  • Residential Property Type
  • 564.44 Price/Sqft
  • 14 Cars Garage
  • 1970 Year Built

Property Description

Set up high on approximately 2 acres in Chatham’s Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home’s appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham’s beaches.

Basic Details

CCIMLS
$2,295,000
$5,655
2026
Residential
For Sale
4
3
1
3.5
8
1970
4,066 Sqft
84,506 Sqft
Active
Single Family Residence
22603375
Coldwell Banker Realty
Janet Stuart

Features

: Natural Gas
: Central Air
: Finished, Full
: Partial
: Patio, Deck
: 14
: Water Heater, Natural Gas
4
: Carpet, Hardwood
2
: Central Vacuum, Recessed Lighting
: Corner Lot
: Paved, Off Street, Direct Access, Garage Door Opener
: Shingle, Asphalt
No
0 - .1

Additional Information

: Contemporary, Cape Cod
: Beach Access
$75
Annually
: Shingle Siding
: Standard
: Public
No
72
10/02/2026

Address Map

55 Winterset Drive
MA
Barnstable
Chatham
02633
0
W70° 1' 22.7''
N41° 41' 39''
Old Queen Anne Road to Winterset Drive, house located at the end on the left.
Great Hills
Property