15 Windy Hill Way, Chatham MA 02633
Chatham, MA 02633 • Chatham (village)
$6,250,000
$5,850,000
Est. $31,733/month
Track this home for price, status, and open-house alerts.
About this home
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.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
Scan with phone
Public Records & Permits
Log in to view assessor & tax records, ownership history, and recent building permits for this property.
BMN Estimate
Get the number an algorithm can't give you
A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.
Recently Sold Nearby
Property History
Market Insights
1
Price Changes
6.4%
Price Range
Property Timeline
Price Reduced
Jun 24, 2026
$5,850,000
$400,000
(-6.4%)
From $6,250,000 to $5,850,000 (-6.4%)
Listed for Sale
Apr 2, 2026
$6,250,000
Original listing
Agent: Timothy Bailey
Office: John C. Ricotta & Associates, Inc.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/24/2026 | ↓ Price Reduced | $5,850,000 | $400,000 | - | From $6,250,000 to $5,850,000 (-6.4%) |
| 04/02/2026 | 🏠 Listed for Sale | $6,250,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $23,421 | $6,596,800 |
Financial Details
Annual Property Tax
$23,421
Tax Year 2026
Assessed Value
$6,596,800
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
2007
Living Area
5,620 sq ft
Lot Size
0.93 acres
Bedrooms
5
Full Baths
5
Half Baths
1
Total Rooms
13
Interior
Heating
Central, Forced Air, Natural Gas
Cooling
Central Air
Flooring
Wood, Tile, Carpet
Appliances
Electric Water Heater, Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator
Fireplace
None
Fireplaces
2
Basement
Full, Finished, Walk-out Access, Interior Entry
Laundry
Electric Dryer Hookup, Washer Hookup
Features
Central Vacuum
Exterior
Construction
Frame
Architecture
Cape, Shingle
Roof
Wood
Features
Porch, Deck, Patio, Pool - Inground, Rain Gutters, Storage, Sprinkler System, Screens, Outdoor Shower, Stone Wall, Outdoor Gas Grill Hookup
Pool
In Ground
Spa
None
Fencing
None
Patio/Porch
Porch, Deck, Patio
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Garage Door Opener, Off Street, Driveway, Stone/gravel
Total Spaces
7
Utilities
Electric
None
Water
Public
Sewer
Private Sewer
Gas
None
Other
For Gas Range, For Gas Oven, For Electric Dryer, Washer Hookup, Outdoor Gas Grill Hookup
Financial
Annual Tax
$23,421
Assessed Value
$6,596,800
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Barnstable
Total market time (incl. prior listings)
88 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
2007
Bedrooms
5
Full Bathrooms
5
Half Bathrooms
1
Living Area
5,620 sq ft
Total Rooms
13
Floor Layout
Interactive room guide
Floor Layout
Finished Area
4,514 sq ft above grade
1,106 sq ft below grade
Display Options
Outdoor Areas
PoolIn Ground
Patio & porchPorch, Deck, Patio
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Tile, Carpet
Appliances:
Electric Water Heater, Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator
Interior Features:
Central Vacuum
Windows:
Screens
Basement:
Full, Finished, Walk-Out Access, Interior Entry
Laundry:
Electric Dryer Hookup, Washer Hookup
Security:
Security System
Construction & Materials
Style:
Cape, Shingle
Year Built:
2007
Structure Type:
Exterior Materials:
Frame
Roof:
Wood
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Central, Forced Air, Natural Gas
Cooling:
Central Air
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Porch, Deck, Patio, Pool - Inground, Rain Gutters, Storage, Sprinkler System, Screens, Outdoor Shower, Stone Wall, Outdoor Gas Grill Hookup
Patio & Porch:
Porch, Deck, Patio
Fencing:
Other Structures:
Lot Features:
Cleared, Level
Road Surface:
Paved
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
7
Parking Features:
Attached, Garage Door Opener, Off Street, Driveway, Stone/Gravel
Special Features
Fireplaces:
2
Fireplace Type:
Pool:
Private Pool
Pool Features:
In Ground
Community Amenities:
Nearby Schools
School information not available for this location.
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$1,952
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
Loading map...
Neighborhood
Chatham (village)
15 Windy Hill Way, Chatham MA 02633
Chatham, MA 02633
Listing Information
Listing Agent
Timothy Bailey
Listing Office
John C. Ricotta & Associates, Inc.
Office Phone
508-945-5000
Agent MLS ID
CN228729
Office MLS ID
AN4535
Listing Data Updated
Jun 28, 2026 4:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
Contact Us
Ask about this property — free, no obligation.
Similar Homes for Sale
Comparable Properties
Customize Comparable Search
Finding comparable properties...
Loading market insights for Chatham.