15 Windy Hill Way
Chatham, MA, 02633
$6,250,000
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.
Current real estate data for Single Family in Chatham as of May 17, 2026
72
Single Family Listed
90
Avg DOM
1,022
Avg $ / SqFt
$3,287,487
Avg List Price
Property Details
Price:
$6,250,000
MLS #:
22601111
Status:
Active
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Apr 1, 2026
Finished Sq Ft:
5,620
Total Sq Ft:
5,620
Lot Size:
40,473 sqft / 0.93 acres (approx)
Year Built:
2007
Schools
School District:
Monomoy
Interior
Appliances
Dishwasher, Washer, Range Hood, Refrigerator, Gas Range, Electric Dryer, Electric Water Heater
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
2
Flooring
Wood, Carpet, Tile
Interior Features
Recessed Lighting, HU Cable TV
Laundry Features
Laundry Room, Recessed Lighting, Second Floor
Main Level Bathrooms
1
Exterior
Architectural Style
Cape Cod, Shingle
Attached Garage YN
1
Community Features
Deeded Beach Rights
Construction Materials
Shingle Siding
Exterior Features
Outdoor Shower
Fencing
Partial
Garage Spaces
2
Lot Features
In Town Location, School, Medical Facility, Major Highway, Near Golf Course, Shopping, Public Tennis, Marina, Level
Open Parking YN
1
Other Structures
Pool House
Parking Features
Basement
Parking Spots
5
Parking Total
5
Patio And Porch Features
Deck, Porch, Patio
Roof
Pitched, Wood
Spa Features
Private, Heated
Stories
2
Window Features
Bay/Bow Windows
Financial
Tax Year
2026
Taxes
$23,421
Map
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Community
- Address15 Windy Hill Way Chatham MA
- CityChatham
- CountyBarnstable
- Zip Code02633
Subdivisions in Chatham
Property Summary
- 15 Windy Hill Way Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $6,250,000 and features 5 beds, 6 baths, and has approximately 5,620 square feet of living space, and was originally constructed in 2007. The current price per square foot is $1,112. The average price per square foot for Single Family listings in Chatham is $1,022. The average listing price for Single Family in Chatham is $3,287,487. To schedule a showing of MLS#22601111 at 15 Windy Hill Way in Chatham, MA, contact your Thomas D Brown R E Associates agent at 508-487-1112.
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Raised in Orleans and now a resident of Truro, Lucy is extremely familiar with life on the Outer Cape. She is experienced in real estate sales on Cape Cod and has been involved in construction, development and real estate for over thirty-five years here on the Outer Cape. She presently handles all facets of marketing for both Brown Associates and Cape Vacation Rentals. Degree in Sales & Marketing; formerly associated with Nickerson Realty Corp. where she handled all phases of land development, a…
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15 Windy Hill Way
Chatham, MA