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Steele Associates Real Estate

15 Windy Hill Way, Chatham, MA 02633 (MLS# 22601111)

15 Windy Hill Way, Chatham, MA 02633

$5,850,000
Property Type: Residential Bedrooms: 5 Baths: 6 Square Footage: 5,620 Lot Size (sq. ft.): 40,473 Status: Active
Current Price: $5,850,000 List Date: 4/01/2026 Last Modified: 8/11/2026

Overview

Description

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.

Listing Details MLS# 22601111

Contract Info

Original List Price
6250000
List Price/SqFt
1040.93

Legal and Taxes

Street #
15
Street Name
Windy Hill
Street Suffix
Way
County
Barnstable
Town
Chatham
Village
Chatham
State
MA
Zip Code
02633
Tax ID
CHAT M:12A B:004B L:C8
Estimated Annual Taxes
23421
Tax Year
2026
Building Assessments
5070200
Other Assessments
55700
Total Assessment
6596800
Land Court Cert #
(178561)
Underground Fuel Tank
No
Lead Base Paint
No
Asbestos
No
Flood Ins Required
No
Mass Use Code
101 - Residential, single family
Nitrogen Sensitive Area
Yes

General Property Info

Region
Lower Cape
School District
Monomoy
Zoning
R40
Property Sub-Type
Single Family Residence
Year Built
2007
Renovated
Yes
Year Renovated
2015
Renovated Comments
Finished Basement. New Furnace 2025
Total Finished Space
5620
Field Card SqFt
4514
Additional Finished Space
1106
Additional SqFt Source
Public Records
Total Rooms
13
Stories
2
Private Pool
Yes
Private Dock
No
Leased Land
No
Lot Size SqFt
40473
Lot Size Source
Assessor
Acres
0.93
Garage
Yes
# of Cars
2
# of Parking Spaces
5
Year Round
Yes
Bedrooms - Total
5
Baths - Full
5
Baths - Half
Yes
Baths - Total
6
Golf Course Front
No
Golf Course View
No
Waterfront
No
Waterview
No
Miles to Beach
.1 - .3
Mi. to Beach Comments
Private access to Stage Harbor
Fireplace
Yes
# Fireplaces
2
Warranty Available
No
Property Includes Recording Devices
No

Baths Per Level

Basement Baths
Yes
Baths - Level 1
Yes
Baths - Level 2
4

Convenient To

Convenient to Water Body 1
Stage Harbor
Convenient to Water Body 2
Oyster Pond
Convenient to Water Body 3
Nantucket Sound

Sewer

Septic Tank Description
Title V Grade Level

More Information

DPR Eligibility

DPR Eligible
No

Room Types

Bedroom 3 Level
Second
Bedroom 4 Level
Second
Dining Room Level
First
Kitchen Level
First

Property Features

Street Description: Paved; Private Special Listing Cond: None Architectural Style: Cape Cod; Shingle Year Built Desc: Actual Basement Description: Finished; Full; Garage Access; Interior Access; Walk-Out Access Foundation Details: Poured Lot Features: Gentle Sloping; Interior Lot; Level; Sloped; Views Neighborhood Amen: Beach Access; Deeded Beach Rights Garage Description: Attached; Direct Access; Garage Door Opener Parking Features: Driveway; Gravel Convenient To: Golf Course; In Town Location; Major Highway; Marina; Medical Facility; Public Tennis; School; Shopping Appliances: Dishwasher; Electric Dryer; Gas Range; Range Hood; Refrigerator; Washer Floors: Carpet; Tile; Wood Interior Features: Central Vacuum; Hot Tubs/Spa; HU Cable TV; Recessed Lighting; Walk-In Closet(s) Patio And Porch Features: Deck; Patio; Porch Private Pool Description: Covered; In Ground; Vinyl Other Structures: Pool House Exterior Features: Hot Tub; Outdoor Shower; Private Yard; Underground Sprinkler System Fencing: Partial Roof Description: Pitched; Wood Siding Description: Shingle Sewer: Septic Tank Heating: Forced Air Cooling: Central Air Fuel Type: Natural Gas Water: Public Hot Water: Water Heater Hot Water Source: Electric Room Types: Bedroom 2; Bedroom 3; Bedroom 4; Bedroom 5; Dining Room; Family Room; Foyer; Kitchen; Laundry; Living Room; Office; Primary Bedroom

Room Information

Room Name Level
Primary Bedroom Second
Bedroom 2 Second
Bedroom 3 Second
Bedroom 4 Second
Foyer First
Laundry Second
Dining Room First
Living Room First
Kitchen First
Bedroom 5 Second
Family Room First
Family Room Basement
Office Second

Documents

IDX
Listing Office: John C Ricotta & Assoc.
Listing Agent: Timothy P Bailey
Source MLS Verified
Last Updated: August - 11 - 2026
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS, Inc include the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS, Inc shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 02/14/2017. All properties are subject to prior sale, changes, or withdrawal. Copyright 2020© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved
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