For sale

Price cut: $400K (6/24)

$5,850,000

15 Windy Hill Way, Chatham, MA 02633

5beds

5,620sqft

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Single Family Residence

Built in 2007

0.93 Acres Lot

$5,340,800 Zestimate^®

$1,041/sqft

$-- HOA

What's special

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.

101 days

1,165

54

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Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 5
Bathrooms: 6
Full bathrooms: 5
1/2 bathrooms: 1
Main level bathrooms: 1

Primary bedroom

Description: Flooring: Wood
Features: Balcony, Recessed Lighting, Closet
Level: Second

Bedroom 2

Description: Flooring: Wood
Features: Bedroom 2, Closet, Recessed Lighting
Level: Second

Bedroom 3

Description: Flooring: Wood
Features: Bedroom 3, Closet, Recessed Lighting
Level: Second

Bedroom 4

Description: Flooring: Wood
Features: Bedroom 4, Balcony, Closet, Private Full Bath, Recessed Lighting
Level: Second

Primary bathroom

Features: Private Full Bath

Dining room

Description: Flooring: Wood
Features: Recessed Lighting, Dining Room
Level: First

Kitchen

Description: Countertop(s): Granite,Flooring: Wood
Features: Kitchen, Breakfast Nook, Built-in Features, Kitchen Island, Pantry, Private Half Bath, Recessed Lighting
Level: First

Living room

Description: Fireplace(s): Gas,Flooring: Wood
Features: Recessed Lighting, Living Room
Level: First

Heating

Has Heating (Unspecified Type)

Cooling

Central Air

Appliances

Included: Dishwasher, Washer, Range Hood, Refrigerator, Gas Range, Electric Dryer, Electric Water Heater
Laundry: Laundry Room, Recessed Lighting, Second Floor

Features

Recessed Lighting, HU Cable TV
Flooring: Wood, Carpet, Tile
Windows: Bay/Bow Windows
Basement: Finished,Interior Entry,Full
Number of fireplaces: 2
Fireplace features: Gas

Interior area

Total structure area: 5,620
Total interior livable area: 5,620 sqft

Property

Parking

Total spaces: 5
Parking features: Basement
Attached garage spaces: 2
Has uncovered spaces: Yes

Features

Stories: 2
Entry location: First Floor
Patio & porch: Deck, Porch, Patio
Exterior features: Outdoor Shower
Has private pool: Yes
Pool features: Pool Cover, Vinyl, In Ground
Has spa: Yes
Spa features: Private, Heated
Fencing: Partial

Lot

Size: 0.93 Acres
Features: In Town Location, School, Medical Facility, Major Highway, Near Golf Course, Shopping, Public Tennis, Marina, Level

Details

Additional structures: Pool House
Parcel number: CHAT M:12A B:004B L:C8
Zoning: R40
Special conditions: None

Construction

Type & style

Home type: SingleFamily
Architectural style: Cape Cod, Shingle
Property subtype: Single Family Residence

Materials

Shingle Siding
Foundation: Poured
Roof: Pitched, Wood

Condition

Updated/Remodeled, Actual
New construction: No
Year built: 2007
Major remodel year: 2015

Utilities & green energy

Sewer: Septic Tank

Community & HOA

Community

Features: Deeded Beach Rights

HOA

Has HOA: No

Location

Region: Chatham

Financial & listing details

Price per square foot: $1,041/sqft
Tax assessed value: $6,596,800
Annual tax amount: $23,421
Date on market: 4/1/2026
Cumulative days on market: 101 days
Road surface type: Paved

Estimated market value

$5,340,800

$5.07M - $5.61M

$7,882/mo

Price history

Date	Event	Price
6/24/2026	Price change	$5,850,000-6.4%$1,041/sqft
Source: CCIMLS #22601111 Report a problem
4/1/2026	Listed for sale	$6,250,000-7.4%$1,112/sqft
Source: CCIMLS #22601111 Report a problem
12/2/2025	Listing removed	$6,750,000$1,201/sqft
Source: MLS PIN #73379321 Report a problem
5/22/2025	Listed for sale	$6,750,000$1,201/sqft
Source: CCIMLS #22502496 Report a problem

Public tax history

Tax history is unavailable.

Monthly payment

Est. payment

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All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.

HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

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