166 Chestnut Street, Blue Mountains, ON L9Y 5T5
Blue Mountains · Near Grey Rd 19/Crosswinds Blvd · View map
About this home
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.
The home
- Type
- 2-storey detached home
- Style
- 2-Storey
- Square footage
- 2500-3000 sq ft
- Bedrooms
- 5
- Basement bedrooms
- 1
- Bathrooms
- 5
- Kitchens
- 1
- Rooms
- 17
- Basement
- Full, Finished
- Lot size
- 49.9 x 115.2 ft
- Faces
- West
- View
- Forest, Pond, Park/Greenbelt
- Approximate age
- 0-5 years
Ownership & fees
- Ownership
- Freehold, with a share in common elements (POTL)
- POTL fee
- $105.00/mo
- Fee includes
- Shared parts of the complex, such as a private road. Ask what it covers.
- Exterior
- Stone, Hardboard
Heating & cooling
- Heating fuel
- Gas
- Heating type
- Forced Air
- Air conditioning
- Central Air
- Fireplace
- Yes
Garage & parking
- Garage
- Attached
- Garage spaces
- 2
- Driveway spaces
- 2
- Total parking
- 4
Taxes & other
- Property taxes
- $6,935/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- Flex
- Cross street
- Grey Rd 19/Crosswinds Blvd
- Neighbourhood
- Blue Mountains
More
- Price per sq ft
- ~$684 (at 2,750 sq ft)
- MLS® number
- X13825876
No matching details. Ask Will instead
The home and its surroundings
- Sump Pump
- Storage
- Golf
- Park
- School Bus Route
- School
- Skiing
- Mortgage
- Property tax
- POTL fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
166 Chestnut Street, Blue Mountains, ON L9Y 5T5
Blue Mountains · Near Grey Rd 19/Crosswinds Blvd
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Listing history for 166 Chestnut Street
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 166 Chestnut Street
Answers come straight from this home’s MLS® listing.
How much is 166 Chestnut Street listed for, and what would it cost each month?
166 Chestnut Street is listed for $1,879,900. With 20% down ($375,980), the mortgage payment would be roughly $7,583 a month at 4.5% over 30 years. Add property tax and the common-element (POTL) fee and the estimate comes to about $8,266 a month, all in. That figure is an illustration, not a quote.
Is 166 Chestnut Street freehold or a condo, and is there a monthly fee?
166 Chestnut Street is a 2-storey detached home in Blue Mountains. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, but the home is a parcel of tied land (POTL) with a common-element fee of $105.00 a month for shared parts of the complex, such as a private road, snow clearing and visitor parking. Ask what it covers before you offer.
How many bedrooms and bathrooms does 166 Chestnut Street have?
166 Chestnut Street has 5 bedrooms, plus 1 more bedroom in the basement, and 5 bathrooms.
Does 166 Chestnut Street have a garage and parking?
Yes. The listing shows the garage as attached, with room for 2 cars. The driveway adds 2 spaces. In total the listing counts 4 parking spaces.
Does 166 Chestnut Street have a finished basement?
The listing describes the basement as full, finished. It counts 1 bedroom on that level. Finished basement space is usually not counted in the square footage shown.
What style of home is 166 Chestnut Street?
166 Chestnut Street is a 2-storey detached home. A 2-storey detached house has its living space on the main floor and the bedrooms upstairs, on its own lot with no shared walls.
How big is 166 Chestnut Street, and what is the lot size?
The listing puts the home between 2,500 and 3,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 49.9 x 115.2 ft.
How is 166 Chestnut Street heated and cooled?
Heating is forced air (gas). Cooling is central air.
What are the property taxes for 166 Chestnut Street?
Property taxes are $6,935 a year (2026), or about $578 a month.
Where is 166 Chestnut Street?
166 Chestnut Street is in Blue Mountains. The nearest main intersection is Grey Rd 19/Crosswinds Blvd. The postal code is L9Y 5T5.
Is 166 Chestnut Street still for sale?
Yes. It is an active listing (MLS® X13825876). Listings here update from the board through the day and come down once a home sells.
What are similar detached homes near 166 Chestnut Street asking?
Similar detached homes for sale nearby right now include 147 Lakeshore Road E at $1,999,000 (5 bed), 118 Timber Lane at $2,050,000 (5 bed) and 156 Chamonix Crescent at $1,449,000 (5 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 166 Chestnut Street sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 166 Chestnut Street?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar detached homes nearby
More detached homes for sale near Blue Mountains, picked by style, size and price.
2-storey detached home$1,999,000147 Lakeshore Road E, Blue Mountains5 bed · 4 bath · Blue MountainsCourtesy of: RE/MAX Four Seasons Realty LimitedView home →
2-storey detached home$2,050,000118 Timber Lane, Blue Mountains5 bed · 5 bath · Blue MountainsCourtesy of: Royal LePage Signature RealtyView home →
2-storey detached home$1,449,000156 Chamonix Crescent, Blue Mountains5 bed · 4 bath · Blue MountainsCourtesy of: CV Real EstateView home →Courtesy of: Bosley Real Estate Ltd.
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. 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.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax and the common-element (POTL) fee. For illustration only.