Salehian.com 647-325-5000

166 Chestnut Street

Blue Mountains, Blue Mountains, L9Y 5T5

$1,879,900

Photo 1 of 47Photo 2 of 47Photo 3 of 47Photo 4 of 47Photo 5 of 47Photo 6 of 47Photo 7 of 47Photo 8 of 47Photo 9 of 47Photo 10 of 47Photo 11 of 47Photo 12 of 47Photo 13 of 47Photo 14 of 47Photo 15 of 47Photo 16 of 47Photo 17 of 47Photo 18 of 47Photo 19 of 47Photo 20 of 47Photo 21 of 47Photo 22 of 47Photo 23 of 47Photo 24 of 47Photo 25 of 47Photo 26 of 47Photo 27 of 47Photo 28 of 47Photo 29 of 47Photo 30 of 47Photo 31 of 47Photo 32 of 47Photo 33 of 47Photo 34 of 47Photo 35 of 47Photo 36 of 47Photo 37 of 47Photo 38 of 47Photo 39 of 47Photo 40 of 47Photo 41 of 47Photo 42 of 47Photo 43 of 47Photo 44 of 47Photo 45 of 47Photo 46 of 47Photo 47 of 47
  • 5+1 bedrooms
  • 5 bathrooms
  • 4 parking
  • 2500-3000 sq ft

Listed 25 days ago · MLS® X13825876

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. Furniture package can be negotiated.

Details

Type
Detached
Style
2-Storey
Age
0-5 years
Size
2500-3000 sq ft
Lot
49.9 × 115.16 ft
Basement
Full, Finished
Garage
Attached
Kitchens
1
Property tax
$6,935 (2026)
Neighbourhood
Blue Mountains
Municipality
Blue Mountains
Price per sq ft
$684 (about the same as detached houses in Blue Mountains)

Interior

Bedrooms
5 above ground + 1 below
Bathrooms
1 × 2-piece, 1 × 5-piece, 2 × 3-piece, 1 × 4-piece
Rooms
17 above ground
Family room or den
Yes
Fireplace
Natural Gas
Features
Sump Pump, Storage

Heating, cooling and services

Heating
Forced Air, Gas
Air conditioning
Central Air
Water and sewer
Sewer

Building and exterior

Style
2-Storey
Exterior
Stone, Hardboard
Roof
Asphalt Shingle
Foundation
Poured Concrete
Age
0-5 years
Faces
West

Parking

Garage spaces
2
Total parking
4

Lot

Size
49.9 × 115.16 ft (rectangular)

More

Possession
Flex
Nearby
Golf, Park, School Bus Route, School, Skiing
Cross street
Grey Rd 19/Crosswinds Blvd

Rooms

RoomLevelSizeFeatures
OfficeMain3.28 × 2.74 m (10'9" × 9')
Dining RoomMain3.28 × 3.96 m (10'9" × 13')
KitchenMain3.2 × 4.88 m (10'6" × 16')
Living RoomMain5.18 × 4.88 m (17' × 16')
LaundryMain4.65 × 3.05 m (15'3" × 10')
Bedroom 5Second6.1 × 4.72 m (20' × 15'6")
Bedroom 2Second2.82 × 3.81 m (9'3" × 12'6")
Bedroom 3Second2.82 × 3.89 m (9'3" × 12'9")
Bedroom 4Second3.28 × 3.96 m (10'9" × 13')
RecreationBasement8.15 × 6.55 m (26'9" × 21'6")
Bedroom 5Basement3.05 × 3.66 m (10' × 12')

Location

Location is approximate. See nearby homes on the map

Recent sales nearby

See what similar homes within 1 km sold for in the last year. Create a free account or sign in to see them.

The neighbourhood

Getting around Car-dependent

No subway, LRT or GO station within a short trip.

Within a 10-minute walk: no grocery stores, 0 cafés and restaurants, 0 parks.

Who lives here postal area L9Y

Owners / renters
75% / 25%
Median household income
$85,000
Average age
48
Children under 15
13%
Homes
60% detached, 3% high-rise
Commute by transit
1%
Population
28,925

Languages spoken most at home besides English: Polish 0.2%, Punjabi (Panjabi) 0.2%, Tagalog (Pilipino, Filipino) 0.1%, Kurdish 0.1%.

Safety

Crime Severity Index for Collingwood (The Blue Mountains) (OPP): 29 vs 57 for Ontario (2025).

Police-reported figures for the whole police service area, not this street. Rates use the area’s resident population.

Distances are approximate. Places © OpenStreetMap contributors. Neighbourhood figures: Statistics Canada, 2021 Census. Crime Severity Index: Statistics Canada.

Living here

Commute

Noise Nothing major nearby

No highway within 500 m, rail line within 300 m, or airport flight path nearby.

Distances from the map, not noise measurements. Visit at rush hour to judge for yourself.

Internet Wireless only

50/10 Mbps or faster available here by wireless only (the federal high-speed target).

From the federal broadband map. Check exact speeds and providers for the address.

Roads, rail, airports and planned stations © OpenStreetMap contributors. Internet: Innovation, Science and Economic Development Canada, National Broadband Data.

Listed by Bosley Real Estate Ltd..

Listing information provided by PropTx Innovations Inc. and TRREB; deemed reliable but not guaranteed accurate by PropTx.

Similar homes nearby

See more in Blue Mountains