5-bed, 5.5-bath single-family home in Chatham

Active$5,850,000

MLS® Listing#22601111 · Single Family Residence · Listed Apr 1, 2026

15 Windy Hill Way, Chatham, MA 02633

Barnstable County

Showing 5 of 93 photos

5Beds

5.5Baths

5,620Sq Ft

2007Year built

0.93Acre lot

2Garage

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.

Full description online — scan the code for the complete listing.

Property information

Property type: Residential
Sub-type: Single Family Residence
Year built: 2007
Living area: 5,620 Sq Ft
Lot size: 0.93 acres
Garage spaces: 2
Annual taxes (2026): $23,421
HOA fee: None
Price / Sq Ft: $1,041
Days on market: 187

Features

Interior: Central Vacuum · Recessed Lighting · Walk-In Closet(s)
Appliances: Dishwasher · Gas Range · Refrigerator · Range Hood
Cooling: Central Air
Heating: Natural Gas
Flooring: Wood · Tile · Carpet
Parking: Direct Access · Garage Door Opener · Driveway · Gravel
Laundry: Laundry Room
Fireplace: Gas
Pool: Pool Cover · Vinyl · In Ground · Private
Patio: Deck · Patio · Porch

$5,850,000List price

5Beds

5.5Baths

5,620Sq Ft

2007Year built

0.93Acre lot

2Garage

6 months agoOn market

$5,850,000

15 Windy Hill Way

Chatham, MA 02633

Active

Your local EXIT Realty office

EXIT Cape Realty (Brewster)Brewster, MACall

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Description

Property Information

Property type: Residential
Sub-type: Single Family Residence
Style: Cape Cod / Shingle
Year built: 2007
Living area: 5,620 Sq Ft
Lot size: 0.93 acres
Garage spaces: 2
Parking spaces: 5
Zoning: R40
Days on market: 187
MLS^® Listing#: 22601111

Property Features

Interior: Central Vacuum · Recessed Lighting · Walk-In Closet(s)
Exterior: Outdoor Shower
Appliances: Dishwasher · Gas Range · Refrigerator · Range Hood · Washer · Water Heater
Cooling: Central Air
Heating: Natural Gas
Flooring: Wood · Tile · Carpet
Fireplace: Gas
Basement: Finished · Full
Pool: Pool Cover · Vinyl · In Ground · Private
Parking: Direct Access · Garage Door Opener · Driveway · Gravel · Attached
Laundry: Laundry Room
Patio: Deck · Patio · Porch
Fencing: Partial
Lot features: Sloped · Gentle Sloping · Interior Lot · Level · Views
Construction: Shingle Siding
Roof: Wood
Windows: Bay Window(s)
Other structures: Pool House
Sewer: Septic Tank
Water source: Public

Rooms

First Floor

Other Room 2
Living Room

Second Floor

Other Room 4
Other Room 1
Laundry

Basement

Other Room 3

Second

Bedroom 1
Bedroom 2
Bedroom 3
Laundry

First

Dining Room
Living Room
Master Bedroom

Financial Details

HOA: None
Annual taxes: $23,421Tax year 2026
Assessed value: $6,596,800
Parcel number: CHAT M:12A B:004B L:C8

Directions

Stage Harbor Road to Champlain Road to Windy Hill Way #15.

Listing Courtesy: John C Ricotta & Assoc. - 5089455000

Presented by: Timothy P Bailey

The data relating to real estate for sale on this site comes from the Broker Reciprocity of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than the brokerage firm owning this website are marked with the IDX Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor the brokerage firm owning this website shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. 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. Copyright ©2026 Cape Cod & Islands Multiple Listing Service, Inc. All Rights Reserved.

Last Updated: 2026-04-01T00:00:00.000Z

Chatham Market Statistics

How this home compares to 96 active listings in Chatham, MA

	Chatham median	This listing
Median listing price	$2,295,000	$5,850,000
Median days on market	52	187
Median Sq Ft	2,586	5,620
Median price / Sq Ft	$868	$1,041

Market statistics compiled from active EXIT Realty® and MLS listings in Chatham, MA.

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Explore commute times from 15 Windy Hill Way, Chatham, MA 02633.

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Comparable nearby listings and their asking prices.

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Connect with a Local Real Estate Expert

Tina Petrova
REALTOR
EXIT Cape Realty (Brewster)
Isabela De Lima
REALTOR
EXIT Cape Realty (Brewster)
Leo de Alba
REALTOR
EXIT Cape Realty (Brewster)
Dave Harris
Broker of Record, Franchisee
EXIT Cape Realty (Brewster)
Christer Holmquist
Sales Representative
EXIT Cape Realty (Brewster)
Conroy Wilson
REALTOR
EXIT Cape Realty (Brewster)

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. Copyright ©2026 MLS Property Information Network, Inc. All Rights Reserved.

Description

Property Information

Property Features

Rooms

First Floor

Second Floor

Basement

Second

First

Financial Details

Directions

Chatham Market Statistics

Commute Calculator

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50 Sylvan WayChatham, MA 02659#73533378

50 Sylvan WaySouth Chatham, MA 02659#22602789

48 Hillcrest RoadChatham, MA 02633#22604112

5 Hillcrest LaneChatham, MA 02650#22604664

60 Harbor Hill RdChatham, MA 02633#73511079

60 Harbor Hill RoadChatham, MA 02633#22601737

Similar Home Values

Connect with a Local Real Estate Expert

Tina Petrova

Isabela De Lima

Leo de Alba

Dave Harris

Christer Holmquist

Conroy Wilson

Chatham Market Statistics

More homes to consider

50 Sylvan WayChatham, MA 02659#73533378

50 Sylvan WaySouth Chatham, MA 02659#22602789

48 Hillcrest RoadChatham, MA 02633#22604112

5 Hillcrest LaneChatham, MA 02650#22604664

60 Harbor Hill RdChatham, MA 02633#73511079

60 Harbor Hill RoadChatham, MA 02633#22601737

Similar Home Values