15 Windy Hill Way Chatham, MA ^$ 5,850,000

15 Windy Hill Way

^$ 5,850,000

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15 Windy Hill Way

Chatham, MA, 02633

^$ 5,850,000

Bedrooms5 Baths5.1 Sq 5,620

Monthly Estimate*

^$ 40,404

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Single Family Home for sale in Chatham, MA

for $5,850,000 with 5 bedrooms and 5 full baths, 1 half bath. This 5,620 square foot home was built in 2007 on a lot size of 0.93.

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.

Single Family Active

Price

^$ 5,850,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 23,421

Style

Cape Cod, Shingle

Lot Size

0.93

Year Built

2007

Town/City

Chatham

County/Region

Barnstable

MLS | Web ID

22601111

Features

General

Heating Natural Gas

Cooling Central Air

Roof Pitched Wood

Appliances Dishwasher Gas Range Refrigerator Range Hood Washer Water Heater

Garage Spaces 2

Patio/Porch Features Deck Patio Porch

Architectural Style Cape Cod Shingle

Construction Materials Shingle Siding

Year Built 2007

Stories Count 2

Property Subtype Single Family Residence

Tax Year 2026

Community Features Deeded Beach Rights

County Barnstable

Property Type Residential

Association Amenities Beach Access

Attached Garage true

Garage Y/N true

Other Structures Pool House

Total Rooms 13

Full Baths 5

Status Active

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

City Chatham

MLS Area Chatham

Lot Size Units Acres

Lot Size Square Feet 40473

Spa Features Hot Tubs/Spa

Tax Annual Amount 23421

Home Warranty Y/N false

Building Area Units Square Feet

Standard Status Active

Tax Assessed Value 6596800

Interior

Interior Amenities Central Vacuum HU Cable TV Recessed Lighting Walk-In Closet(s)

Basement Finished Full

Flooring Wood Tile Carpet

Total Fireplaces 2

Air Conditioning Y/N true

Heating Y/N true

Half Baths 1

Laundry Features Electric Dryer

Total Bedrooms 5

Total Baths 6

Exterior

Exterior Amenities Outdoor Shower Hot Tub Underground Sprinkler System

Fencing Partial

Parking Features Direct Access Garage Door Opener Driveway Gravel

Lot Features Gentle Sloping Interior Lot Sloped Level Views

Water Source Public

Total Parking 5

Lot Size Area 0.93

Building Area Total 5620

Lot Size Acres 0.93

Waterfront Y/N false

* Excluded Features

List By

Timothy P Bailey

Listing Agent

John C Ricotta & Assoc.

Broker

timbailey1@verizon.net

Affordability Calculator

$42,356

Per Month

Monthly Principal & Interest: $40,404
Monthly Property Taxes: $1,952
Monthly Home Insurance: --

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Down Payment

Loan Term

Interest Rate

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Yearly Home Insurance

Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Chatham, MA

Average List Price ^$3,210,716

Percent of Sale Price 45%

About Chatham, MA

6,037 Population

-10% Since 2002

^$69,389 Median Income

60.04 Median Age

13% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

0 Elementary School

0 Middle School

Unknown High School High School

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Pricing History

Date	Price	Price Change	Description
8/11/2026	$5,850,000		Listed Price

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15 Windy Hill Way, Chatham, MA, 02633 is a Single Family Home for sale at $5,850,000 with 5,620 sqft and a lot size of 0.93. 15 Windy Hill Way has 5 bedrooms, 5.1 baths, and was built in 2007. The property's zip code is 02633 which is in Chatham, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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 Weichert Realtors include the name of the listing broker company. Neither the listing company nor Weichert Realtors 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.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 10/17/2026. All properties are subject to prior sale, changes, or withdrawal.

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15 Windy Hill Way

Single Family Home for sale in Chatham, MA

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