NewFor Sale

166 Chestnut Street
Blue Mountains, Grey County, ON, L9Y 5T5

Detached
TRREB
MLS® Number: X13825876
Estimated Value
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$1,879,900List Price
5+1Bedrooms
5Bathrooms
2Garages
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Current valuation for 166 Chestnut Street, Blue Mountains, ON L9Y 5T5. Listed for $1,879,900 on 2026-11-02

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Description

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.

Features

GolfParkSchool Bus RouteSchoolSkiing

Amenities

No amenities available

Summary

Tax:$6,935 / 2026
Listing #:X13825876
Property Type:Detached, 2-Storey
Building Age:0-5
Size:2500-3000 feet²
Land Size:49.9 x 115.16
Days on CPRB:
Garage:Attached 2 garage
Locker:None
On CPRB Since:
Listing Brokerage:Bosley Real Estate Ltd.

Rooms

Details

Property

Property Type:Detached
Style:2-Storey
Community:Blue Mountains
Municipality:Grey County

Building

Size:2500-3000 feet²
Building Age:0-5
Construction:Stone, Hardboard

Inside

Bedrooms:5+1
Bedrooms Above Grade:5
Bathrooms:5
Kitchens:1
Family Room:Yes
Appliances Included:Sump Pump, Storage
Basement:Full, Finished

Parking

Garage Type:Attached
Garage Spaces:2
Total Parking Spaces:4

Utilities

Cooling:Central Air
Heating Type:Forced Air
Heating Fuel:Gas
Utility Sewer:Sewer

Highlights

Fireplace Type:Natural Gas

Land

Cross Street:Grey Rd 19/Crosswinds Blvd

$1,879,900

List price

166 Chestnut Street, Blue Mountains – Detached for sale · MLS® # X13825876