Loading

166 Chestnut Street Blue Mountains, Ontario L9Y 5T5

166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 1 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 2 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 3 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 4 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 5 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 6 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 7 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 8 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 9 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 10 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 11 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 12 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 13 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 14 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 15 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 16 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 17 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 18 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 19 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 20 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 21 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 22 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 23 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 24 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 25 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 26 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 27 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 28 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 29 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 30 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 31 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 32 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 33 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 34 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 35 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 36 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 37 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 38 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 39 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 40 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 41 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 42 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 43 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 44 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 45 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 46 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 1 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 2 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 3 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 4 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 5 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 6 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 7 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 8 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 9 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 10 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 11 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 12 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 13 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 14 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 15 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 16 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 17 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 18 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 19 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 20 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 21 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 22 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 23 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 24 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 25 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 26 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 27 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 28 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 29 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 30 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 31 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 32 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 33 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 34 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 35 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 36 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 37 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 38 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 39 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 40 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 41 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 42 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 43 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 44 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 45 - X13825876
166 Chestnut Street, Blue Mountains, Ontario L9Y 5T5 - Photo 46 - X13825876

$1,879,900

Maintenance, Parcel of Tied Land

$105 Monthly

6 Bedroom 5 Bathroom 2,500 - 3,000 ft2
Fireplace Central Air Conditioning Forced Air

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:36109)

Virtual Tour

Property Details

MLS® Number X13825876
Property Type Single Family
Community Name Blue Mountains
Amenities Near By Golf Nearby, Park, Schools, Ski Area
Community Features School Bus
Equipment Type Water Heater - Tankless, Water Heater
Features Sump Pump
Parking Space Total 4
Rental Equipment Type Water Heater - Tankless, Water Heater

Building

Bathroom Total 5
Bedrooms Above Ground 5
Bedrooms Below Ground 1
Bedrooms Total 6
Age 0 To 5 Years
Amenities Fireplace(s)
Appliances Dishwasher, Dryer, Microwave, Stove, Washer, Wine Fridge, Refrigerator
Basement Development Finished
Basement Type Full (finished)
Construction Style Attachment Detached
Cooling Type Central Air Conditioning
Exterior Finish Stone, Hardboard
Fireplace Present Yes
Fireplace Total 2
Foundation Type Poured Concrete
Half Bath Total 1
Heating Fuel Natural Gas
Heating Type Forced Air
Stories Total 2
Size Interior 2,500 - 3,000 Ft2
Type House
Utility Water Municipal Water

Parking

Attached Garage
Garage

Land

Acreage No
Land Amenities Golf Nearby, Park, Schools, Ski Area
Sewer Sanitary Sewer
Size Depth 115 Ft ,2 In
Size Frontage 49 Ft ,10 In
Size Irregular 49.9 X 115.2 Ft
Size Total Text 49.9 X 115.2 Ft
Zoning Description R1-3-62-h19

Rooms

Level Type Dimensions
Second Level Bedroom 5 6.1 m x 4.72 m
Second Level Bedroom 2 2.82 m x 3.81 m
Second Level Bedroom 3 2.82 m x 3.89 m
Second Level Bedroom 4 3.28 m x 3.96 m
Basement Recreational, Games Room 8.15 m x 6.55 m
Basement Bedroom 5 3.05 m x 3.66 m
Main Level Office 3.28 m x 2.74 m
Main Level Dining Room 3.28 m x 3.96 m
Main Level Kitchen 3.2 m x 4.88 m
Main Level Living Room 5.18 m x 4.88 m
Main Level Laundry Room 4.65 m x 3.05 m

Utilities

Cable Installed
Electricity Installed
Sewer Installed
INQUIRE ABOUT
166 Chestnut Street
First Name(Required)
Last Name
This REALTOR.ca listing content is owned and licensed by REALTOR® members of The Canadian Real Estate Association

The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademark DDF® is owned by The Canadian Real Estate Association (CREA) and identifies CREA's Data Distribution Facility (DDF®)


The Lakelands Association of REALTORS®

Bosley Real Estate Ltd.

September 24 2026 09:01:19

RealtyPress WordPress CREA DDF® Plugin

Cookies
We serve cookies. If you think that's ok, just click "Accept all". You can also choose what kind of cookies you want by clicking "Settings".
Settings Accept all
Cookies
Choose what kind of cookies to accept. Your choice will be saved for one year.
Save Accept all