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

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

About this home

Renovated and expanded Contemporary Cape at the end of a cul-de-sac on just under two acres allows for a unique amount of privacy while being less than a five minute drive to Chatham Village, Chatham Lighthouse, the Chatham Bars Inn and all that Chatham has to offer. As part of Great Hill Estates, this home has deeded rights to Lover's Lake for swimming, kayaking and canoeing. This home offers large open spaces perfect for entertaining and large gatherings. The first floor has a family room with vaulted beamed ceiling and wood burning fireplace open to a kitchen with large island and dining area, another large living room with gas fireplace open to a wraparound deck for grilling, dining and enjoying the views of nature looking out over the property. Enjoy a first floor primary with ensuite bathroom including laundry and a half bath. Upstairs are two more bedrooms, one as a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath. The lower level has a bedroom, a full bath, second laundry, and walk-out access to a stone patio with custom stone seating area and a built-in gas fire-pit. Features including central a/c, hardwood floors, two car attached garage, brand new Bosch heating system and newer roof. Just steps away from the Cape Cod Rail Trail Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73548377
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
108
On market date
July 11, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
2
Parking spaces
10
Lot size
1.94 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

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, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 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
Google Places 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 108 days -- 28 fewer days than Chatham's current average of 136 days.
For reference, the median list price across 99 active listings in Chatham right now is $1,650,000.

Mortgage calculator

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

Adjust tax / insurance estimates
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. Last updated 10 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.