Single Family Residence at 55 Winterset Drive, Chatham MA 02633, Chatham
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$2,295,000

55 Winterset Drive, Chatham MA 02633
Chatham, MA 02633
Listed by Janet Stuart
Bedrooms
4
Bathrooms
3.5
Living area
4,072 sqft
Year built
1970

About this home

Set on 1.9 acres at the end of a quiet cul-de-sac in Chatham, this unique home occupies the corner and offers privacy, a natural setting, and wraparound decks. The property has deeded rights to Lovers Lake for kayaking, canoeing and swimming just steps away. Inside, the home features beamed ceilings, hardwood floors, and an abundance of windows and doors, many of which are new. The first floor includes two great rooms, an open kitchen with granite countertops, island seating and a large dining area, plus a primary bedroom with en-suite full bath, laundry, and ample closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level includes a bedroom, full bath, laundry, and access to a stone patio with fire pit and built-in stone seating. The home has central air conditioning throughout, a newer Bosch heating system, and a new roof. Conveniently located near Chatham Village, the bike path, and Chatham beaches.

Highlights

Fireplace

Property details

MLS #
73548377
Property type
Single Family Residence
Subdivision
Great Hill
Status
Active
Days on market
75
On market date
July 11, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
2
Parking spaces
14
Lot size
1.94 acres
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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

Walkability

Blended score for Chatham's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

76
Walkable
out of 100
EPA National Walkability Index
13.7 / 20 -- Above average walkable
Nearby-amenity density
87 / 100
Restaurants & cafes13
Grocery stores3
Parks11
Schools3
Transit stops2
Pharmacies1

Market position

How this listing compares to current activity in Chatham, from live MLS data.

On the market 75 days -- 56 fewer days than Chatham's current average of 131 days.
For reference, the median list price across 87 active listings in Chatham right now is $2,150,000.

Mortgage calculator

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Est. monthly payment
$13,971/mo
$459,000 down
$1,836,000 loan
Principal & interest$11,908
Property tax (est.)$1,913
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 8 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.