
15 Windy Hill Way Chatham — Photo 1 of 42
Recent Drop: $400,000
$5,850,000
Chatham, MA 02633 — Chatham (village)
Beds
5
Baths
5.5
SqFt
5,620
Style
Single Family
Built
2007
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.
* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Chatham, MA.
Electric Water Heater • Water Heater • Range • Dishwasher • Microwave • Refrigerator • Washer • Dryer • Wine Refrigerator
Was $6,250,000
Jun 24, 2026
MLS® 73495151
Apr 1, 2026
MLS® 73495151
Dec 2, 2025
MLS® 73379321
May 22, 2025
MLS® 73379321
4,512
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$85K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
15.9%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
513 housing units permitted in the last 12 months (-50% vs the prior 12 months) — 128 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 5,620 sq ft principal dwelling). Lot size: 40,510 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Timothy Bailey
Listing Office: John C. Ricotta & Associates, Inc.
MLS® Number: 73495151
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