362 Winston Road
1020 - WO West · Oakville · ON · L6L 4W5
Listed yesterday
About this property
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.
Key facts
See this home in person
Free, no commitment. The agent confirms the time with you.
Open houses
No upcoming open houses.
Property details
Rooms & baths
- Kitchens
- 1
- Den / Family room
- Yes
- Rooms above / below grade
- 11
- Bedrooms above / below
- 3
- Washrooms
- 1 × 4-pc · Main
- 1 × 3-pc · Ground
- 1 × 5-pc · Second
- 1 × 3-pc · Basement
Basement
- Basement
- Crawl Space, Full, Unfinished, Finished
Fireplace
- Fireplace
- Yes (2 · Natural Gas)
Heating & cooling
- Heat
- Forced Air · Gas
- A/C
- Central Air
Finishes & appliances
- Central vacuum
- Yes
Interior features
- Central Vacuum
- Water Heater Owned
- Auto Garage Door Remote
Outdoor
- Direction faces
- West
Construction
- Construction
- Stucco (Plaster)
- Roof
- Asphalt Shingle
- Foundation
- Concrete Block
Parking & garage
- Garage
- Attached · 4
- Covered spaces
- 4
- Total
- 8
- Features
- Private, Private Double
Utilities
- Sewer
- Sewer
- Water
- Municipal
Lot
- Width / Depth
- 75.1 ft · 155.9 ft
Taxes & fees
- Taxes
- $9,004/2026
Included & excluded
- Inclusions
- 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.
- Exclusions
- Oval mirror in primary bedroom.
Overview
- Property type
- Detached
- Style
- Bungalow
- Age
- 51-99
- Possession
- Flexible
- Cross street
- Rebecca/Fourth Line
Mortgage calculator
Location
Cross street: Rebecca/Fourth Line
Market Overview
Oakville
Listing data provided by the Toronto Regional Real Estate Board (TRREB).
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The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. 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.
Last updated: October 27, 2026.