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, an exceptional South Oakville residence situated on one of the area's most prestigious and highly sought-after streets, surrounded by stunning custom-built multi-million-dollar homes. Just a short walk to the renowned Appleby College, this beautifully renovated bungalow offers an outstanding blend of elegance, comfort, and convenience. Thoughtfully updated and impeccably maintained, the home features a substantial rear addition showcasing a spacious family room with a cozy gas fireplace and a walkout to the private west-facing backyard. Large windows adorned with solid wood California shutters fill the home with natural light, while hardwood flooring throughout the main level adds warmth and timeless appeal. The updated kitchen overlooks the mature backyard and features a skylight that floods the space with sun. Adjacent to the kitchen, a charming breakfast nook with a bay window provides the perfect spot for casual dining, while a separate formal dining room offers an elegant setting for entertaining. Privately located on the upper level, the impressive primary retreat features a spacious sitting area, skylight, generous closet space, and a 5-piece ensuite. Two additional bedrooms and a 4-piece bathroom complete the main floor. The finished lower level expands the living space with a large recreation room, office, gym or potential additional bedroom, laundry area, abundant storage, and another full bathroom. With four full bathrooms throughout the home, there is plenty of room for family and guests. Outside, a rare oversized attached four-car garage and a private west-facing backyard offer exceptional outdoor enjoyment, mature landscaping, and beautiful sunset views. Ideally located close to high-ranking public and private schools, parks, transit, shopping, and major highways, this solidly built home presents a rare opportunity to own in one of South Oakville's most desirable enclaves.
The home
- Type
- 1 1/2 storey
- Style
- 1 1/2 Storey
- 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
- ~$877 (at 2,250 sq ft)
- Listed
- Sep 25, 2026 · 17 days ago
- MLS® number
- W13830254
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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 $1,974,000. With 20% down ($394,800), the mortgage payment would be roughly $7,963 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $8,713 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 1 1/2 storey 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 1 1/2 storey. A 1½-storey home has a full main floor and a partial second floor under the roofline, often with dormer windows.
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.
How long has 362 Winston Road been on the market?
362 Winston Road was listed on September 25, 2026. It has been on the market for 17 days. It is an active listing (MLS® W13830254). Listings here update from the board through the day and come down once a home sells.
What are similar bungalows near 362 Winston Road asking?
Similar bungalow-style homes for sale nearby right now include 1119 Rebecca Street at $1,999,000 (3 bed), 499 Valley Drive N at $1,398,000 (4 bed) and 1373 Hixon Street at $1,775,000 (3 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 647-619-2256.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar bungalows nearby
More bungalow-style homes for sale near 1020 - WO West, picked by style, size and price.
1 1/2 storey$1,999,0001119 Rebecca Street, Oakville3 bed · 3 bath · 1020 - WO WestCourtesy of: ROYAL LEPAGE SIGNATURE REALTYView home →
1 1/2 storey$1,398,000499 Valley Drive N, Oakville4 bed · 2 bath · 1020 - WO WestCourtesy of: SUTTON GROUP QUANTUM REALTY INC.View home →
1 1/2 storey$1,775,0001373 Hixon Street, Oakville3 bed · 2 bath · 1017 - SW SouthwestCourtesy of: ROYAL LEPAGE CERTIFIED REALTYView home →Courtesy of: Royal LePage Realty Plus Oakville, Brokerage
PropTx MLS® assumes no responsibility for the accuracy of any information shown. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.