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Single Family Residence at 15 Windy Hill Way, Chatham MA 02633, Chatham
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42 photos

$5,850,000

15 Windy Hill Way, Chatham MA 02633
Chatham, MA 02633
Listed by Timothy Bailey
Bedrooms
5
Bathrooms
5.1
Living area
5,620 sqft
Year built
2007

About this home

This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

Highlights

Private poolFireplace

Property details

MLS #
73495151
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
149
On market date
April 1, 2026
Stories
N/A
Total bathrooms
6
Garage spaces
2
Parking spaces
7
Lot size
0.93 acres

Location

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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Chatham Elementary School
1.27 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
1.73 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
5.15 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

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Est. monthly payment
$35,379/mo
$1,170,000 down
$4,680,000 loan
Principal & interest$30,354
Property tax (est.)$4,875
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 28, 2026.

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.