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166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains
  • 166 CHESTNUT STREET The Blue Mountains

166 CHESTNUT STREET, The Blue Mountains, Ontario

$1,879,900

  • 6 Beds
  • 5 Baths

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:56241)

  • Listing ID: X13825876
  • Property Type: Single Family
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Rooms

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

Details

  • Amenities Nearby: Golf Nearby, Park, Schools, Ski area
  • Community Features: School Bus
  • Equipment: Water Heater - Tankless, Water Heater
  • Features: Sump Pump
  • Maintenance Fee: 105.00
  • Maintenance Fee Type: Parcel of Tied Land
  • Maintenance Fee Payment Unit: Monthly
  • Ownership: Freehold
  • Parking Spaces: 4
  • Rental Equipment: Water Heater - Tankless, Water Heater
  • Transaction: For sale
  • Zoning Description: R1-3-62-H19

Building

  • Amenities: Fireplace(s)
  • Appliances: Dishwasher, Dryer, Microwave, Stove, Washer, Wine Fridge, Refrigerator
  • BasementType: Full (Finished)
  • Basement Development: Finished
  • Bedrooms Main Level: 5
  • Bedrooms Lower Level: 1
  • Construction Style Attachment: Detached
  • Cooling: Central air conditioning
  • Exterior Finish: Stone, Hardboard
  • Fireplace Present: True
  • Fireplace Total: 2
  • Foundation: Poured Concrete
  • Bathrooms (Half): 1
  • Bathrooms (Total): 5
  • Heating: Forced air
  • Heating Fuel: Natural gas
  • Size Interior: 2500 - 3000 sqft
  • Stories Total: 2
  • Type: House
  • Utility Water: Municipal water

Land

  • Amenities: Golf Nearby, Park, Schools, Ski area
  • Sewer: Sanitary sewer
  • Size Frontage: 49 ft ,10 in
  • Size Irregular: 49.9 x 115.2 FT
MLS®

Listing provided by Bosley Real Estate Ltd.
MLS®, REALTOR®, and the associated logos are trademarks of the Canadian Real Estate Association.

REALTOR®

This REALTOR.ca listing content is owned and licensed by REALTOR® members of the Canadian Real Estate Association. This property for sale is located at 166 CHESTNUT STREET in The Blue Mountains Ontario. It was last modified on September 24th, 2026. Contact Sheila Shepherd to schedule a viewing or to discover other The Blue Mountains homes for sale.

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