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166 Chestnut Street in Blue Mountains for sale

Asking price
$1,879,900
Estimate (Sep 24)
$1,757,996
MLS #:
X13825876
Type:
Detached, 2-Storey
Approx. SQFT:
2500-3000
Basement:
Full, Finished
5+1 5+1
2 49.9 x 115.16 ft lot
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.

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  • Date Listed: Thursday, September 24, 2026
  • Listing Brokerage: Bosley Real Estate Ltd. - Disclaimer: The information contained in this listing has not been verified by Bosley Real Estate Ltd. and should be verified by the buyer.
  • Virtual Tour: View Virtual Tour for 166 Chestnut Street
  • City: Blue Mountains

    More 5 bedrooms homes for sale in Blue Mountains

  • Neighbourhood: Blue Mountains
  • Major Intersection: Grey Rd 19/Crosswinds Blvd
  • Full Address: 166 Chestnut Street, Blue Mountains, L9Y 5T5, ON, Canada
  • Kitchen:
  • Living Room:
  • Amenities:
  • Taxes: $6,935.00 (2026)
Office11 x 9 ft99 sq ft
Dining11 x 13 ft143 sq ft
Kitchen10 x 16 ft160 sq ft
Living17 x 16 ft272 sq ft
Laundry15 x 10 ft150 sq ft
5th Br20 x 15 ft300 sq ft
13 x 16 ft208 sq ft
2nd Br9 x 12 ft108 sq ft
3rd Br9 x 13 ft117 sq ft
4th Br11 x 13 ft143 sq ft
Rec27 x 21 ft567 sq ft
5th Br10 x 12 ft120 sq ft
  • Sunday - October 04 12:00 - 4:00 PM

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WHAT'S YOUR HOME WORTH?

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