Scout N Secure

$1,879,900

Map

166 Chestnut Street

Blue Mountains, Ontario L9Y5T5

For sale· Added

5+1 bed5 bath2,500–3,000 sqft

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

OfficeMain level3.28 x 2.74 m
Recreational, Games roomBasement8.15 x 6.55 m
Bedroom 5Basement3.05 x 3.66 m
Dining roomMain level3.28 x 3.96 m
KitchenMain level3.2 x 4.88 m
Living roomMain level5.18 x 4.88 m
Laundry roomMain level4.65 x 3.05 m
Bedroom 5Second level6.1 x 4.72 m
Bedroom 2Second level2.82 x 3.81 m
Bedroom 3Second level2.82 x 3.89 m
Bedroom 4Second level3.28 x 3.96 m

Ask about this home

$1,879,900
166 Chestnut Street
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