For sale 50$1,879,900
166 Chestnut Street
Blue Mountains, Ontario L9Y5T5
For sale· Added
About this home
A rare expression of design, setting and four-season living in Windfall.One of only ten homes backing directly onto the pond and expansive green space, this exceptional residence enjoys a coveted 115-foot-deep lot and nearly 4,000 sq. ft. of beautifully finished living space. With its rare walkout basement, generous scale and thoughtful design, this is a home that feels distinctly different from the rest.The main living spaces are beautifully appointed with a custom kitchen featuring a 36-inch commercial-style gas range, bespoke laundry room, designer lighting and high-end plumbing fixtures sourced through Georgian Design Center. The upper level offers five bedrooms, including two expansive suites that each feel like a private primary retreat, complete with ensuites and walk-in closets. The principal primary suite elevates the experience further with a custom built-in closet and an oversized glass shower. A fifth bedroom offers flexibility as a guest room, office or dedicated media room.Every detail, down to the custom drapery has been intentionally selected to create a home that feels sophisticated, warm and effortlessly livable.The walkout lower level extends the living space with a huge family room, built-in wet bar, 108-bottle wine fridge, full bathroom and additional bedroom currently styled as a home gym. Outside, a massive deck and covered porch overlook the pond and green space, complemented by a full irrigation system for effortless landscaping and maintenance.Featured in Our Homes Magazine in Summer 2025, the home reflects a level of design and finish that is immediately evident.And then there is Windfall - pools, The Shed, walking trails and an effortless connection to Blue Mountain and the surrounding landscape, all just moments from the Village and ski hills.A truly special opportunity to own one of Windfall's most distinctive homes, in one of its most coveted settings.
Location
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Property details
Listing
- MLS® number
- X13825876
- Added
- Sep 24, 2026 ()
- Updated
- Oct 5, 2026 ()
- Info refreshed
Overview
- Property type
- Single Family
- Building type
- Detached
- Storeys
- 2
- Ownership
- Freehold
Inside
- Bedrooms
- 5+1
- Bathrooms
- 5
- Half baths
- 1
- Heating
- Forced air, Natural gas
- Cooling
- Central air conditioning
- Fireplace
- Yes (2)
- Appliances
- Washer, Refrigerator, Dishwasher, Wine Fridge, Stove, Dryer, Microwave
- Features
- Sump Pump
Building
- Basement
- Finished, Full
- Exterior
- Stone, Hardboard
- Foundation
- Poured Concrete
- Parking
- Attached Garage, Garage · 4 spaces
- Amenities
- Fireplace(s)
Land
- Lot size
- 49.9 x 115.2 ft
- Zoning
- R1-3-62-H19
Services
- Water
- Municipal water
- Sewer
- Sanitary sewer
- Utilities
- Sewer, Electricity, Cable
Location
- Cross streets
- Grey Rd 19/Crosswinds Blvd
- Directions
- Grey Rd 19 to Crosswinds Blvd to Sugar Maple Street to Chestnut Street.
- Nearby
- School Bus
Running costs
- Annual property tax
- $6,935
- Condo fee
- $105 Monthly
- Includes Parcel of Tied Land
Rooms
| Office | Main level | 3.28 x 2.74 m |
| Recreational, Games room | Basement | 8.15 x 6.55 m |
| Bedroom 5 | Basement | 3.05 x 3.66 m |
| Dining room | Main level | 3.28 x 3.96 m |
| Kitchen | Main level | 3.2 x 4.88 m |
| Living room | Main level | 5.18 x 4.88 m |
| Laundry room | Main level | 4.65 x 3.05 m |
| Bedroom 5 | Second level | 6.1 x 4.72 m |
| Bedroom 2 | Second level | 2.82 x 3.81 m |
| Bedroom 3 | Second level | 2.82 x 3.89 m |
| Bedroom 4 | Second level | 3.28 x 3.96 m |
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