15 Windy Hill Way
Chatham, MA, 02633
$5,850,000
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 Aug 16, 2026
56
Single Family Listed
111
Avg DOM
1,126
Avg $ / SqFt
$3,081,957
Avg List Price
Property Details
Price:
$5,850,000
MLS #:
22601111
Status:
Active
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
chatham
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
Interior
Appliances
Dishwasher, Gas Range, Refrigerator, Range Hood, Washer, Water Heater
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
2
Flooring
Wood, Tile, Carpet
Heating
Natural Gas
Interior Features
Central Vacuum, HU Cable TV, Recessed Lighting, Walk-In Closet(s)
Laundry Features
Electric Dryer, Laundry Room
Exterior
Association Amenities
Beach Access
Attached Garage YN
1
Community Features
Deeded Beach Rights
Construction Materials
Shingle Siding
Exterior Features
Outdoor Shower, Hot Tub, Underground Sprinkler System
Fencing
Partial
Garage Spaces
2
Lot Features
Gentle Sloping, Interior Lot, Sloped, Level, Views
Other Structures
Pool House
Parking Features
Direct Access, Garage Door Opener, Driveway, Gravel
Parking Spots
5
Parking Total
5
Patio And Porch Features
Deck, Patio, Porch
Roof
Pitched, Wood
Spa Features
Hot Tubs/Spa
Stories
2
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 $5,850,000 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 $1,041. The average price per square foot for Single Family listings in Chatham is $1,126. The average listing price for Single Family in Chatham is $3,081,957. 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