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.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
Bungalow
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, outdoor umbrella.
Listed by Royal LePage Realty Plus Oakville, Brokerage
Data was last updated October 26, 2026 at 10:15 PM (UTC)
Area Statistics
Listings on market:
103
Avg list price:
$1,999,900
Min list price:
$924,900
Max list price:
$6,199,000
Avg days on market:
39
Min days on market:
1
Max days on market:
228
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.