$2,390,000
4 Bed
3 Bath
4,066 Sqft Building
84,506 Sqft Lot

55 Winterset Drive, Chatham, Massachusetts 02633

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

Property Description

Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and 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. Home is being offered fully furnished if desired.

Basic Details

CCIMLS
$2,390,000
$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

: Hot Water
: Central Air
: Finished, Full, Interior Entry
: Partial
: Patio, Deck
: 14
: Gas Water Heater
: French
4
: Carpet, Hardwood
2
: Recessed Lighting
: Laundry Room, First Floor
: Major Highway, Cul-de-sac, Bike Path, Conservation Area, Near Golf Course, House Of Worship, Marina, Medical Facility, School, Shopping, Cape Cod Rail Trail, Public Tennis
: Basement
: Shingle, Asphalt
: Dining Room, Recessed Lighting, Shared Half Bath
: Living Room, Cathedral Ceiling(s), Recessed Lighting, Beamed Ceilings, Shared Half Bath
: Private Full Bath
: Septic Tank
No
0 - .1

Additional Information

: Contemporary, Cape Cod
$75
Annually
: Shingle Siding
: Poured
: Actual, Updated/remodeled
: Standard
: Well
R60
No
33
08/14/2026

Address Map

55 Winterset Drive
MA
Barnstable
Chatham
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