166 Chestnut Street, Blue Mountains, ON

Blue Mountains, Blue Mountains Hood
Grey Rd 19/Crosswinds Blvd
5+1 Br | 5 Bath | 2500-3000 Sqft
$1,879,900 For Sale

Property Overview

  • Detached — 2-Storey
  • SqFt: | 2500-3000 Sqft
  • Lot Size: 49.90 x 115.16 Feet
  • Age: 0-5 Years
  • Basement: Full, Finished
  • Exterior: Stone, Hardboard
  • Taxes: 6,935 / 2026
  • Zoning: n/a
  • MLS #: X13825876
  • Sewer: Sewer
  • Heat Source: Gas , Forced Air

Property Description

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.

Fridge, Stove, Dishwasher, Microwave, Washer Dryer, Bar Fridge, Wine Fridge, Light Fixtures, Drapery, irrigation system

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 2-Storey
  • Lot: 49.90 x 115.16 Feet
  • Region: Grey County
  • Hood: Blue Mountains
  • Zoning: n/a
  • Lot Irreg: Fronting on: West
  • Fronting On: West

Building Details

  • Age: 0-5 Years
  • Exterior: Stone, Hardboard
  • Heat: Gas , Forced Air
  • A/C: Central Air
  • Interior Features: Sump Pump, Storage
  • Pool: None
  • Sewer: Sewer
  • Garage: Attached
  • Total Parking: 4.00

Property Interior

  • Sqft: 2500-3000 Sqft
  • Bed: 5 +1
  • Bath: 5
  • Kitchen: 1
  • Family Room: No
  • Basement: Full, Finished
Rooms Details

Office

Main Level

3.28 x 2.74

Dining Room

Main Level

3.28 x 3.96

Kitchen

Main Level

3.2 x 4.88

Living Room

Main Level

5.18 x 4.88

Laundry

Main Level

4.65 x 3.05

Bedroom 5

Second Level

6.1 x 4.72

Second Level

3.96 x 4.88

Bedroom 2

Second Level

2.82 x 3.81

Bedroom 3

Second Level

2.82 x 3.89

Bedroom 4

Second Level

3.28 x 3.96

Recreation

Basement Level

8.15 x 6.55

Bedroom 5

Basement Level

3.05 x 3.66

Property Listed by: Bosley Real Estate Ltd.
Virtual Tour: n/a

Home Valuation Estimate

What is 166 Chestnut Street, Blue Mountains, ON worth in today’s Blue Mountains, Blue Mountains market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 5-bedroom Detached with 2500-3000 sq. ft. in Blue Mountains, Blue Mountains. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 166 Chestnut Street
  • Neighborhood: Blue Mountains
  • Zip/Postal Code: L9Y 5T5
  • Nearby Amenities: Golf, Park, School Bus Route, School, Skiing
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About 166 Chestnut Street, Blue Mountains, ON L9Y 5T5, Blue Mountains

Located at 166 Chestnut Street, Blue Mountains, ON in Blue Mountains (Blue Mountains neighbourhood), near Grey Rd 19/Crosswinds Blvd. This freehold home offers Detached, ["2-Storey"], 5 bedrooms, 5 bathrooms and 2500-3000 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Full, Finished • 4 parking spots • Garage: Attached • Heating: Gas Forced Air • Cooling: Central Air. Property taxes are approximately $6,935 for 2026. 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 priv.

FAQs for 166 Chestnut Street, Blue Mountains, ON , Blue Mountains , Blue Mountains

What are the listing details for 166 Chestnut Street, Blue Mountains, ON?
166 Chestnut Street, Blue Mountains, ON is a Detached for sale in Blue Mountains, in the Blue Mountains neighbourhood, Grey County. The current list price is $1,879,900. MLS number: X13825876.
How many bedrooms and bathrooms does this home have?
166 Chestnut Street, Blue Mountains, ON is listed as a Detached with a ["2-Storey"] style, featuring 5+1 bedroom(s) and 5 bathroom(s). The listed interior size range is 2500-3000 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 49.90 x 115.16 Feet. The basement is listed as: Full, Finished. Garage type: Attached. Total parking: 4 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Forced Air. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Stone, Hardboard.
Where is this property located?
166 Chestnut Street, Blue Mountains, ON is located in the Blue Mountains neighbourhood of Blue Mountains. The listed cross street is Grey Rd 19/Crosswinds Blvd.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $6,935 / 2026. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.