Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 2 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 3 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 4 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 5 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 6 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 7 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 8 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 9 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 10 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 11 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 12 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 13 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 14 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 15 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 16 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 17 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 18 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 19 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 20 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 21 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 22 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 23 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 24 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 25 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 26 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 27 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 28 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 29 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 30 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 31 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 32 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 33 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 34 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 35 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 36 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 37 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 38 of 39
Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham, photo 39 of 39
39 photos

$2,390,000

55 Winterset Drive, Chatham MA 02633
Chatham, MA 02633
Listed by Janet Stuart
Bedrooms
4
Bathrooms
3.1
Living area
4,072 sqft
Year built
1970

About this home

Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to 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, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

Highlights

Fireplace

Property details

MLS #
73548377
Property type
Single Family Residence
Subdivision
Great Hill
Status
Active
Days on market
48
On market date
July 11, 2026
Stories
N/A
Total bathrooms
4
Garage spaces
2
Parking spaces
14
Lot size
1.94 acres
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Chatham Elementary School
0.95 mi away · Grades 0-4
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
145
Student:teacher ratio
8.5:1
District
Monomoy Regional School District
Middle
Monomoy Regional Middle School
0.3 mi away · Grades 5-7
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
456
Student:teacher ratio
10.9:1
District
Monomoy Regional School District
High
Monomoy Regional High School
4.66 mi away · Grades 8-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
670
Student:teacher ratio
11.0:1
District
Monomoy Regional School District

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$14,543/mo
$478,000 down
$1,912,000 loan
Principal & interest$12,401
Property tax (est.)$1,992
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 6 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.