166 Chestnut Street, Blue Mountains, ON L9Y 5T5

About this property

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.

Property facts & features

Property type

Detached

MLS® number

X13825876

Source status

New

Bedrooms

6

Bathrooms

5

Reported interior area

Not provided

Neighbourhood

Not provided

Postal code

L9Y 5T5

Parking spaces

4

Garage

Attached

Lot depth (source units)

115.16

Annual property tax

6935

Basement

Full, Finished

Laundry

Not provided

Interior features

Sump Pump, Storage

Exterior features

Not provided

Values and units are reported by the listing source. Verify measurements and fees with the brokerage.

Floor plans & room measurements

Floor plans and verified room measurements are not available for this property.

Property value & listing history

Multi-event history, valuations and sold comparables require verified property identity and display permissions. No historical events or estimated values have been inferred.

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Planning estimate with Canadian semiannual compounding. Excludes mortgage insurance, closing costs and special assessments. This is not a lender quote or mortgage approval.

Location & neighbourhood

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