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.
About this home
Photos of 362 Winston Road
Facts and features of 362 Winston Road
| Type | Detached |
|---|---|
| Style | Bungalow |
| Bedrooms | 3 |
| Bathrooms | 4 |
| Size | 2000-2500 sq ft |
| Lot | 75.13 x 155.94 Feet |
| Parking | 8 |
| Garage | Attached |
| Heating | Forced Air |
| Cooling | Central Air |
| Basement | Crawl Space, Full, Unfinished, Finished |
| Exterior | Stucco (Plaster) |
| Age | 51-99 |
| Taxes | $9,004 (2026) |
| Days on market | 4 |
| Listing brokerage | Royal LePage Realty Plus Oakville, Brokerage |
Rooms
17 rooms, with sizes
| Room | Level | Size | Features |
|---|---|---|---|
| Bedroom 2 | Main | 13′ 7″ × 11′ 3″ 4.13 × 3.44 m | |
| Bathroom | Ground | 10′ 8″ × 5′ 1″ 3.25 × 1.54 m | 3 Pc Bath |
| Bathroom | Main | 6′ 6″ × 4′ 11″ 1.99 × 1.51 m | 4 Pc Bath |
| Dining Room | Main | 16′ 3″ × 7′ 8″ 4.96 × 2.33 m | |
| Recreation | Basement | 14′ 6″ × 10′ 8″ 4.42 × 3.26 m | |
| Bathroom | Second | 11′ 1″ × 5′ 0″ 3.37 × 1.52 m | 5 Pc Ensuite |
| Laundry | Basement | 26′ 11″ × 8′ 0″ 8.21 × 2.45 m | |
| Breakfast | Main | 12′ 0″ × 8′ 9″ 3.66 × 2.66 m | |
| Family Room | Ground | 17′ 4″ × 15′ 7″ 5.29 × 4.76 m | |
| Kitchen | Main | 11′ 8″ × 9′ 8″ 3.56 × 2.94 m | |
| Bathroom | Basement | 6′ 6″ × 6′ 1″ 1.98 × 1.85 m | 3 Pc Bath |
| Primary Bedroom | Second | 21′ 1″ × 19′ 4″ 6.43 × 5.89 m | |
| Office | Basement | 11′ 7″ × 10′ 8″ 3.53 × 3.26 m | |
| Bedroom 3 | Main | 13′ 7″ × 9′ 0″ 4.15 × 2.74 m | |
| Living Room | Main | 15′ 4″ × 9′ 10″ 4.67 × 2.99 m | |
| Den | Basement | 14′ 10″ × 10′ 8″ 4.53 × 3.26 m | |
| Other | Main | 8′ 11″ × 4′ 1″ 2.72 × 1.25 m |
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362 Winston Road
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362 Winston Road
Listing information is deemed reliable but is not guaranteed accurate by PropTx or the Toronto Regional Real Estate Board. Data source: PropTx. Listings are refreshed from the MLS® at least daily.
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.
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MLS® W14117948 Data source: PropTx Listed October 26, 2026