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Photo 1 of 166 Chestnut Street, Blue Mountains — HOMEH
Photo 1 of 166 Chestnut Street, Blue Mountains — HOMEH
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For Sale
Walk-Out BasementLarge Lot
Listed for:Listed 25 days ago
$1,879,900

166 Chestnut Street

Blue Mountains, ON L9Y 5T5

Detached House For Sale
Kim Karimi
Kim Karimi

Real Estate Broker

416-838-3031
Down Payment AssistanceGet Best Mortgage Rates

Sale & Price History for 166 Chestnut Street, Blue Mountains

No listing history available

Real estate boards require you to or to see the full details of this property.

*Sold prices and complete sale & price history are regulated data. Under the Trust in Real Estate Services Act, 2002 (TRESA) and the rules of the Real Estate Council of Ontario (RECO), and pursuant to the Multiple Listing Service® rules of the Canadian Real Estate Association (CREA) and the Toronto Regional Real Estate Board (TRREB), this information may be shown only to registered users who have agreed to the applicable terms of use (a Virtual Office Website, or "VOW," arrangement). HOMEH Inc., Brokerage therefore provides it to signed-in members only. Creating an account is free and takes under a minute.

About 166 Chestnut Street, Blue Mountains

Summarized Description

  • Rare walkout basement enhances living space.
  • Custom kitchen with high-end appliances.
  • Five spacious bedrooms with ensuites.
  • Expansive green space and pond views.
  • Oversized glass shower in primary suite.
  • Built-in wet bar and wine fridge.
  • Massive deck and covered porch for outdoor living.
  • Proximity to Blue Mountain and ski hills.

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. Furniture package can be negotiated.

Key Facts & Features

Property Costs

Annual Property Tax Amount
$6,935
Land Transfer Tax Fee
$34,073

Rental Items

Rental Equipment
HWT
Under Contract
On Demand Water Heater

Basement Type
Full, Finished

Interior Features

Laundry Level
Main Level
Interior Extras
Sump Pump, Storage
View
Forest, Pond, Park/Greenbelt
Fireplace/Stove
Yes
Fireplace Features
Natural Gas
Elevator
No

Exterior Features

Pool
None
Property Features
Golf, Park, School Bus Route, School, Skiing

Building

Building Type
Detached
Building Style
2-Storey
Approx Age
0-5

Construction

Exterior Finish
Stone, Hardboard
Roof
Asphalt Shingle
Foundation Details
Poured Concrete
Special Designation
Unknown

Lot

Lot Front
49.90 ft
Lot Depth
115.16 ft
Lot Shape
Rectangular

Inclusions

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

Exclusions

Exclusions
Fan in Primary Bedroom

Parking & Garages

Garage Type
Attached
Garage Spaces
2
Parking Spaces
2
Total Garage And Parking Spaces
4

Heating & Cooling

Heat Source
Gas
Heat Type
Forced Air
Air Conditioning
Central Air
Water
Municipal
Sewers
Sewer
Natural Gas
Yes
Hydro
Yes
Cable
Yes
Telephone
Yes

Bedrooms
5 + 1
Washrooms
5
Kitchens
1
Family / bonus room
Yes

Room sizes

  • Kitchen—
    Main level
  • Laundry—
    Main level
  • Recreation—
    Basement level
  • Bedroom 3—
    Second level
  • Living Room—
    Main level
  • Bedroom 5—
    Second level
  • Dining Room—
    Main level
  • Bedroom 5—
    Basement level
  • Bedroom 2—
    Second level
  • Bedroom 4—
    Second level
  • Room—
    Second level
  • Office—
    Main level

Washrooms

  • 2-piece
  • 5-piece
  • 3-piece
  • 4-piece

Municipality
Blue Mountains
Neighbourhood
Blue Mountains
Main cross streets
Grey Rd 19/Crosswinds Blvd
Zoning
R1-3-62-H19
Directions
Grey Rd 19 to Crosswinds Blvd to Sugar Maple Street to Chestnut Street

MLS® number
X13825876
Data source
Toronto Regional Real Estate Board
Listed on
2026-09-24
Updated on
2026-10-16
Days on market
25 days
Possession type
Flexible
Co-op commission
2%
Seller
Listed by
BOSLEY REAL ESTATE LTD.

Home Market Value

Current home valuation for 166 Chestnut Street, Blue Mountains, Blue Mountains, ON. Listed for $1,879,900

HOMEH Estimate

?

$1,711,849

Estimated Sales Range

?

$1,547,894 - $1,958,290

HOMEH Estimate for 166 Chestnut Street, Blue Mountains

Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.

$1,711,849Low confidence
Based on 11 comparable properties
+ $168,051 (10%) above our estimate
See the full analysisFree Every recent nearby sale behind this number

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Blue Mountains, ON
Minimum Down Payment Required:20.0%

20% required for homes $1.5M or more

Minimum down payment

$375,980

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Land Transfer Tax

Provincial

$34,073

Total Land Transfer Tax

$34,073

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