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.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
1 1/2 Storey
Approx. Age:
51-99
Total Approx Floor Area:
2000-2500
Lot Depth:
155'11"47.5 m
Lot Frontage:
75'1½"22.9 m
Direction Faces:
West
Bedrooms:
3
Bathrooms:
4.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
3
Kitchens Above Grade:
1
Rooms Above Grade:
11
Zoning:
RL2-0
Heating type:
Forced Air
Heating Fuel:
Gas
Fireplaces:
2
Foundation:
Concrete Block
Roof:
Asphalt Shingle
Basement:
Crawl Space, Full, Unfinished, Finished
Fireplace Features:
Natural Gas
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
4.0
Parking Features:
Private, Private Double
Parking Spaces:
4
Total Parking Spaces:
8.0
Family Room:
Yes
Possession Details:
Flexible
Pool:
None
Link:
No
HST Applicable To Sale Price:
Included In
Assessment:
$1,042,000
Assessment Year:
2025
Taxes:
$9,003.51 /
2026
Assessment:
$1,042,000.00 /
2025
Halton
Oakville
1020 - WO West
Central Vacuum, Water Heater Owned, Auto Garage Door Remote
All window coverings, electrical light fixtures, washing machine and dryer, upright freezer in basement, bar fridge, central vac & attachments, Maytag oven, dishwasher, Kitchenaid fridge, over the range hood, on the counter microwave, alarm system (owned), bathroom mirrors, Hot water heater (owned), GDO + remotes.
Listed by Royal LePage Realty Plus Oakville, Brokerage
Data was last updated September 25, 2026 at 09:08 PM (UTC)
Area Statistics
Listings on market:
100
Avg list price:
$1,999,995
Min list price:
$924,900
Max list price:
$5,399,000
Avg days on market:
35
Min days on market:
0
Max days on market:
718
These statistics are generated based on the current listing's property type
and located in
1020 - WO West. Average values are
derived using median calculations. This data is not produced by
the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.