$1,974,000
For sale: Detached

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.
Sold data
Detached homes in Oakville (WO West) took a median of 28 days to sell over the last 90 days, with the quickest quarter selling within 13 days and the slowest quarter taking more than 50, across 308 recorded sales.
That clock counts only the listing each home finally sold on. Measured from the first time these properties came to market, including any earlier listings that were withdrawn and re-entered, the median is 70 days.
The median sale price was $1,649,900.
Homes sold for about 4.6% below asking on average, so there was room to negotiate.
About 12% of sales closed above the list price.
Around 20% of sellers reduced their price before finding a buyer.
Based on 308 recorded sales in the last 90 days. Aggregate statistics only; individual sale prices are not shown.
Schools
Oakville (WO West) has 56 Fraser Institute–rated schools (45 elementary and 11 secondary), averaging 7.8/10.
School ratings from the Fraser Institute's Ontario school report cards.
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