$1,679,900
2455 Rebecca Street, Oakville, ON L6L 2B1
West
Listing courtesy of RE/MAX ESCARPMENT REALTY INC.
West · L6L 4W5
$1,799,900
$900 / sq ft1 weeks on market
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.
17 rooms. Dimensions as published by the listing brokerage.
| Room | Level | Dimensions | Features |
|---|---|---|---|
| Living Room | Main | 4.67 × 2.99 m15.3 × 9.8 ft | — |
| Dining Room | Main | 4.96 × 2.33 m16.3 × 7.6 ft | — |
| Kitchen | Main | 3.56 × 2.94 m11.7 × 9.6 ft | — |
| Breakfast | Main | 3.66 × 2.66 m12.0 × 8.7 ft | — |
| Bedroom 2 | Main | 4.13 × 3.44 m13.5 × 11.3 ft | — |
| Bedroom 3 | Main | 4.15 × 2.74 m13.6 × 9.0 ft | — |
| Bathroom | Main | 1.99 × 1.51 m6.5 × 5.0 ft | 4 Pc Bath |
| Other | Main | 2.72 × 1.25 m8.9 × 4.1 ft | — |
| Family Room | Ground | 5.29 × 4.76 m17.4 × 15.6 ft | — |
| Bathroom | Ground | 3.25 × 1.54 m10.7 × 5.1 ft | 3 Pc Bath |
| Primary Bedroom | Second | 6.43 × 5.89 m21.1 × 19.3 ft | — |
| Bathroom | Second | 3.37 × 1.52 m11.1 × 5.0 ft | 5 Pc Ensuite |
| Laundry | Basement | 8.21 × 2.45 m26.9 × 8.0 ft | — |
| Bathroom | Basement | 1.98 × 1.85 m6.5 × 6.1 ft | 3 Pc Bath |
| Recreation | Basement | 4.42 × 3.26 m14.5 × 10.7 ft | — |
| Den | Basement | 4.53 × 3.26 m14.9 × 10.7 ft | — |
| Office | Basement | 3.53 × 3.26 m11.6 × 10.7 ft | — |
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What this home costs beyond the asking price, and how that price compares to what else is on the market.
This home is priced in line with comparable listings — about 45% of comparable detached listings in West are asking less.
Based on 93 comparable active detached listings in West. These are asking prices, not sale prices.
Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.
Payable on closing, on top of the purchase price.
An estimate on the asking price of $1,799,900. Rates current as of September 2026; confirm the final figure with your real estate lawyer.
Listing courtesy of Royal LePage Realty Plus Oakville, Brokerage. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.
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