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15 Windy Hill Way

Chatham, MA 02633

Offered at$5,850,000

Residential · Active · MLS #73495151
Listing Courtesy of John C. Ricotta & Associates, Inc. | Timothy Bailey

5Bedrooms
6Bathrooms
5,620Square feet
2007Year built

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MLS PIN data

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.

Property information

Details at a glance

Interior

Rooms
13
Heating
Central, Forced Air, Natural Gas
Cooling
Central Air
Flooring
Wood, Tile, Carpet
Fireplaces
2

Building

Style
Single Family Residence
Year built
2007
Garage
2
Parking
7
Foundation
Concrete Perimeter
Roof
Wood

Land & utilities

Lot size
0.93 acres
Water
Public
Sewer
Private Sewer
Zoning
R40

Financial

Annual taxes
$23,421
Assessment year
2026

Listing history

Price and status timeline

  1. Ter

    $6,750,000 · May 22, 2025

Property value estimate

An informed starting point

Estimated value$6,870,968

Estimated range $5,960,776$7,781,160

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Sold Jul 10, 2026$5,325,000

2 Blanchard Road

Photo insights

Condition signals

Overall presentationabove average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Chatham

MetricThis propertyChatham
List price$5,850,000$2,850,000105% above local
Price / sq ft$1,041$1,1459% below local
Days on market88913% below local
Explore homes in Chatham

Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.

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Common questions

About 15 Windy Hill Way

Can I schedule a private showing?

Yes. Request a tour of 15 Windy Hill Way and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.