15 Windy Hill Way Chatham — Photo 1 of 42
Recent Drop: $400,000
$5,850,000
Investment Analysis — 15 Windy Hill Way
Chatham, MA 02633 — Chatham (village)
Based on HUD Small Area Fair Market Rent for Barnstable Town, MA MSA, a 5-bedroom in 02633 carries an estimated $3,400/mo in gross rent — about a 0.13% cap rate and $7,587/yr in estimated NOI at the $5,850,000 list price. Adjust every assumption in the calculator below.
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.
ADU Potential
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Electric Water Heater • Water Heater • Range • Dishwasher • Microwave • Refrigerator • Washer • Dryer • Wine Refrigerator
Geography
Property History
$5,850,000
Was $6,250,000
Jun 24, 2026
MLS® 73495151
$6,250,000
Apr 1, 2026
MLS® 73495151
$6,750,000
Dec 2, 2025
MLS® 73379321
$6,750,000
May 22, 2025
MLS® 73379321
Listing Agent: Timothy Bailey
Listing Office: John C. Ricotta & Associates, Inc.
MLS® Number: 73495151