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.
For sale
$6,750,000
15 Windy Hill Way, Chatham, MA 02633
5beds
5,620sqft
Est.:
Single Family Residence
Built in 2007
0.93 Acres Lot
$6,141,200 Zestimate®
$1,201/sqft
$-- HOA
What's special
Swimming poolYacht clubLarge deckDedicated laundry roomHot tubDining roomFinished basement
- 78 days
- on Zillow |
- 1,774 |
- 75 |
Zillow last checked: 7 hours ago
Listing updated: August 08, 2025 at 10:56am
Listed by:
Timothy P Bailey 508-237-3274,
John C Ricotta & Assoc.
Source: CCIMLS,MLS#: 22502496

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
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: 1
- 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: 12A4BC8
- Zoning: R40
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: 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: $1,201/sqft
- Tax assessed value: $6,749,600
- Annual tax amount: $23,421
- Date on market: 5/22/2025
- Road surface type: Paved
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