For sale

Price cut: $400K (6/24)

$5,850,000

15 Windy Hill Way, Chatham, MA 02633

5beds

5,620sqft

$34,496/mo

Get pre-qualified

Single Family Residence

Built in 2007

0.93 Acres Lot

$5,447,100 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.

154 days
958
37

Facts & features

Interior

Bedrooms & bathrooms

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

Heating

Natural Gas

Cooling

Central Air

Appliances

Included: Dishwasher, Gas Range, Refrigerator, Range Hood, Washer, Water Heater
Laundry: Electric Dryer, Laundry Room

Features

Central Vacuum, HU Cable TV, Recessed Lighting, Walk-In Closet(s)
Flooring: Wood, Tile, Carpet
Basement: Finished,Full
Number of fireplaces: 2

Interior area

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

Property

Parking

Total spaces: 5
Parking features: Direct Access, Garage Door Opener, Driveway, Gravel
Attached garage spaces: 2
Has uncovered spaces: Yes

Features

Stories: 2
Patio & porch: Deck, Patio, Porch
Exterior features: Outdoor Shower, Hot Tub, Underground Sprinkler System
Has spa: Yes
Spa features: Hot Tubs/Spa
Fencing: Partial

Lot

Size: 0.93 Acres
Features: Gentle Sloping, Interior Lot, Sloped, Level, Views

Details

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

Construction

Type & style

Home type: SingleFamily
Property subtype: Single Family Residence

Materials

Shingle Siding
Roof: Pitched,Wood

Condition

Year built: 2007

Utilities & green energy

Water: Public

Community & HOA

Community

Features: Deeded Beach Rights

HOA

Has HOA: Yes
Amenities included: Beach Access

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: 134 days

Estimated market value

$5,447,100

$5.17M - $5.72M

$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