166 CHESTNUT STREET, Blue Mountains
6 BEDS · 5 BATHS · 2500 - 3000 sqft
$1,879,900
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. Furniture package can be negotiated.
General Info
| MLS Listing ID: X13825876 | Bedrooms: 6 | Bathrooms: 5 | Year Built: 0 |
| Listing Type: Single Family | Half Baths: 1 | Fireplace Fuel: N/A | Maintenance Fee: 105.00 |
| Foundation: Poured Concrete | Roof: N/A | Title To Land: Freehold | Parking Space Total: 4 |
| Parking: N/A | Heating: Forced air | Size: 2500 - 3000 sqft | Air Conditioning : Central air conditioning |
| Home Style: N/A | Finished Floor Area: N/A | Fireplaces: N/A | Basement: Full (Finished) |
| Water Supply: Municipal water | Road Type: N/A | Pool Type: N/A |
Amenities/Features
- Sump Pump















































