15 Windy Hill Way
Chatham, MA · $6,250,000
Zillow ↗
📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

15 Windy Hill Way

Chatham, MA 02633
$6,250,000
7 days on market · Listed Apr 1, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
View on Zillow ↗
Type
SF
Beds
5
Baths
5.5
Sq Ft
5,620
Acres
0.93
Year Built
2007
$ / Sq Ft
$1,112
Days on Market
7

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$33,406
Cash Flow / yr
$-280,243
Cash-on-Cash
-16%
Cash Required
$1,750,000
Projected Revenue / yr
$184,328
Avg Daily Rate
$1,010
Occupancy
50%
STR Range (P50)
$135,097
🟢 LOW RISK — Registration required with town clerk. No current caps.
STR revenue range: $86,528$186,963

Location & Nearby

Map of 15 Windy Hill Way, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🚤 Battlefield Road Town Landing (Champlain Flats)
    0.32 mi
  • B
    Stage Harbor Yacht Club
    0.37 mi
  • C
    🍦 Buffy's Ice Cream
    0.45 mi
  • D
    🚤 Bridge Street Town Landing
    0.60 mi
  • E
    Stage Harbor Marina (Chatham)
    0.65 mi
  • F
    🚤 Sears Road Town Landing
    0.81 mi
  • G
    🚤 Stage Harbor Boat Ramp
    0.84 mi
  • H
    🚤 Vineyard Avenue Town Landing
    1.01 mi

About this property

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.

Similar listings in Chatham

📋 Chatham Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Chatham
Listed by Timothy P Bailey, John C Ricotta & Assoc.