362 Winston Road, Oakville, ON L6L 4W5
1020 - WO West, Oakville · Near Rebecca/Fourth Line · View map
About this home
Welcome to 362 Winston Road, a sophisticated South Oakville residence situated on a coveted street surrounded by custom multimillion-dollar homes, and walking distance from Appleby College. This deceptively large, renovated bungalow features an amazing, multi-level rear addition that dramatically expands its square footage and provides distinct, functional living zones. The heart of the addition is a spacious ground-floor family room with a gas fireplace, large windows, and a direct walk-out to a private, west-facing backyard. Positioned on its own dedicated upper level, the expansive primary bedroom retreat serves as a private sanctuary complete with a sitting area, skylight, generous closet space, and a 5-piece ensuite. The original main level accommodates daily living with hardwood floors, solid wood California shutters, an updated skylit kitchen, a breakfast nook, a formal dining room, two additional bedrooms, and a 4-piece bathroom. The home's footprint extends into a fully finished lower level, significantly increasing functional space with a large recreation room, home office, gym, laundry area, full 3-piece bathroom, and extensive storage. With four full bathrooms distributed throughout, the layout effortlessly accommodates families and guests. Externally, the property features a rare, oversized attached four-car garage and mature landscaping. This property offers a rare blend of space, privacy, and location in one of South Oakville's premier enclaves.
The home
- Type
- Detached bungalow
- Style
- Bungalow
- Square footage
- 2000-2500 sq ft
- Bedrooms
- 3
- Bathrooms
- 4
- Kitchens
- 1
- Rooms
- 11
- Basement
- Crawl Space, Full, Unfinished, Finished
- Lot size
- 75.1 x 155.9 ft
- Faces
- West
- Approximate age
- 51-99 years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Stucco (Plaster)
Heating & cooling
- Heating fuel
- Gas
- Heating type
- Forced Air
- Air conditioning
- Central Air
- Fireplace
- Yes
- Central vacuum
- Yes
Garage & parking
- Garage
- Attached
- Garage spaces
- 4
- Driveway spaces
- 4
- Total parking
- 8
- Parking features
- Private, Private Double
Taxes & other
- Property taxes
- $9,004/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- Flexible
- Cross street
- Rebecca/Fourth Line
- Neighbourhood
- 1020 - WO West
More
- Price per sq ft
- ~$800 (at 2,250 sq ft)
- MLS® number
- W14117948
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The home and its surroundings
- Central Vacuum
- Water Heater Owned
- Auto Garage Door Remote
- Mortgage
- Property tax
- Maintenance 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.
362 Winston Road, Oakville, ON L6L 4W5
1020 - WO West, Oakville · Near Rebecca/Fourth Line
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Listing history for 362 Winston Road
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 362 Winston Road
Answers come straight from this home’s MLS® listing.
How much is 362 Winston Road listed for, and what would it cost each month?
362 Winston Road is listed for $1,799,900. With 20% down ($359,980), the mortgage payment would be roughly $7,260 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $8,011 a month, all in. That figure is an illustration, not a quote.
Is 362 Winston Road freehold or a condo, and is there a monthly fee?
362 Winston Road is a detached bungalow in 1020 - WO West, Oakville. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 362 Winston Road have?
362 Winston Road has 3 bedrooms and 4 bathrooms.
Does 362 Winston Road have a garage and parking?
Yes. The listing shows the garage as attached, with room for 4 cars. The driveway adds 4 spaces. In total the listing counts 8 parking spaces.
Does 362 Winston Road have a finished basement?
The listing describes the basement as crawl space, full, unfinished, finished. Finished basement space is usually not counted in the square footage shown.
What style of home is 362 Winston Road?
362 Winston Road is a detached bungalow. A detached bungalow has all of its main living space, including the bedrooms, on one floor, usually over a full basement.
How big is 362 Winston Road, and what is the lot size?
The listing puts the home between 2,000 and 2,500 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 75.1 x 155.9 ft.
How is 362 Winston Road heated and cooled?
Heating is forced air (gas). Cooling is central air.
What are the property taxes for 362 Winston Road?
Property taxes are $9,004 a year (2026), or about $750 a month.
Where is 362 Winston Road?
362 Winston Road is in the 1020 - WO West community of Oakville. The nearest main intersection is Rebecca/Fourth Line. The postal code is L6L 4W5.
Is 362 Winston Road still for sale?
Yes. It is an active listing (MLS® W14117948). Listings here update from the board through the day and come down once a home sells.
What are similar detached homes near 362 Winston Road asking?
Similar detached homes for sale nearby right now include 384 Ashbury Road at $1,599,000 (3+1 bed), 412 Sandmere Place at $1,590,000 (3+5 bed) and 357 Morden Road at $1,575,000 (3+2 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 362 Winston Road 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 362 Winston Road?
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 1020 - WO West, picked by style, size and price.
Detached bungalow$1,599,000384 Ashbury Road, Oakville3+1 bed · 2 bath · 1020 - WO WestCourtesy of: GLOBAL BRICKS EXECUTIVE HOMES REALTYView home →
Detached bungalow$1,590,000412 Sandmere Place, Oakville3+5 bed · 5 bath · 1020 - WO WestCourtesy of: MASTER`S TRUST REALTY INC.View home →
Detached bungalow$1,575,000357 Morden Road, Oakville3+2 bed · 2 bath · 1020 - WO WestCourtesy of: RE/MAX GOLD REALTY INC.View home →Courtesy of: Royal LePage Realty Plus Oakville, Brokerage
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. For illustration only.