$ 1,879,900

166 Chestnut Street, Blue Mountains

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. (id:1945)
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Property details for 166 Chestnut Street, Blue Mountains

Type
Residential
Bedrooms
6
Bathrooms
5
Lot Size
49.9 x 115.2 FT
Stories
2
Basement
Finished, Full
Parking
Attached Garage, Garage
Heating
Forced air, Natural gas
Cooling
Central air conditioning
Exterior
Stone, Hardboard
Ownership
Freehold
Annual Taxes
$6,935
Condo Fee
$105 / Monthly

Nearby Listings Stat

Estimated price and comparable properties near 166 Chestnut Street

Active Listings
11
Min Price
$1,299,900
Max Price
$2,999,999
Avg Price
$1,927,245
Days on Market
55
days
Sold Listings
1
Min Sold Price
$1,698,000
Max Sold Price
$1,698,000
Avg Sold Price
$1,698,000
Days until Sold
46
days

Neighbourhood Census Data

The Blue Mountains, Ontario

Population
566
Median Age
60.3
Median Income
$48,725
Dwelling Value
$599,516

Housing Tenure

Owners 90%
Renters 10%

Age Distribution

Dwelling Types

Commute Mode

Education Level

Housing Age

Commute Duration

Avg Household Size: 1.9
Pop. Density: 163.5/km²
Avg Shelter Cost: $1,620/mo
Owners with Mortgage: 52.2%
Owners Spending 30%+: 24.4%
Tenants Spending 30%+: 0%
English only: 90.4%
English and French: 9.6%
Median Household Income: $95,744
Median Employment Income: $28,992

Price History

Listed
September 24, 2026
by Bosley Real Estate Ltd.
Current Price
$1,879,900
Type
Residential
For Sale
166 Chestnut Street

Contact Agent Get in touch about 166 Chestnut Street, Blue Mountains

JUSTIN BOCK
JUSTIN BOCK
Bosley Real Estate Ltd.