
Welcome to this remarkable 1 1/2 Storey detached located in the coveted neighborhood of West. Expertly crafted featuring premium stucco (plaster) construction, this residence presents an exceptional opportunity offered at $2,100,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.
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.
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This detached home located at 362 Winston Road, Oakville is currently for sale and has been available on SousaSells for 0 days. This property is listed at $2,100,000 with an estimated mortgage of $6,990* per month. It has 3 beds, 4 bathrooms, and is 2000-2500 square feet. 362 Winston Road, Oakville is in the West neighborhood.
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* Estimated mortgage assumes a 30% down payment, 4.00% interest rate, and 30-year amortization.Yes! Featuring 3 bedrooms and 4 bathrooms, this home offers ample space and comfort for growing families in West, Oakville.
Families, couples, or downsizers looking for a well-proportioned home in Oakville.
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No historical data available for this property.
This could be the first listing for this address.
If you are looking for a house in Oakville or researching Oakville real estate for sale, this 3-bedroom detached at 362 Winston Road, Oakville, ON offers an exceptional opportunity to buy a home in Oakville, Ontario. Whether you are a first-time Oakville home buyer or comparing active Oakville MLS® homes for sale, working with a dedicated Oakville buyer agent ensures you receive priority showing access, unrepresented buyer protection, and aggressive price negotiation.
Browse all verified Oakville real estate listings, compare active Oakville houses for sale, and view brand new MLS® inventory before it hits the open market.
Under Ontario REBBA/TRESA regulations, the listing brokerage is legally bound to the seller's financial interests. Work with an experienced Oakville realtor & real estate broker who represents you 100%—at zero cost to you as a buyer.
Estimated mortgage: $6,990*/month*. Estimated Ontario Land Transfer Tax: $38,975. First-time Oakville home buyers may qualify for up to $8,475 in rebates.
The current listing price for 362 Winston Road, Oakville, ON in West, Oakville is $2,100,000.
This property features 3 bedrooms and 4 bathrooms across approximately 2000-2500 sqft.
362 Winston Road, Oakville, ON is a Detached (1 1/2 Storey) featuring a Crawl Space, Full, Unfinished, Finished basement.
Interior highlights include: Central Vacuum, Water Heater Owned, Auto Garage Door Remote.
Yes, this property offers parking space for 8.0 vehicles (Attached).
Heating is provided via Gas and cooling via Central Air.
West Oak Trails, Oakville
16 assaults (50.0/100k)
14 B&E (43.8/100k)
22 thefts (68.8/100k)
Improving vs previous year
Formula: (Annual Occurrences / Population) Ă— 100,000. This standard policing calculation normalizes incident frequencies across different population sizes, allowing accurate safety comparisons between quiet residential pockets and dense urban centres.
Disclaimer: Crime and safety analytics are compiled from official municipal and regional police open data records for general consumer informational and demographic research purposes only. Data is deemed reliable but is not guaranteed and does not constitute a legal representation or guarantee of future safety.
Data-driven valuation for 362 Winston Road, Oakville, ON L6L 4W5
Based on 0 recent similar sales in the pocket.
Properties in this area are selling at a steady pace.
Calculate your monthly payment, minimum downpayment, and land transfer taxes for this home in Oakville.
About Purchasing a Home in Oakville, ON
For a property listed at $2,100,000 in Oakville, the legal minimum down payment is $420,000 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.
Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $38,975 for this transaction. As this listing is in Oakville (outside the City of Toronto), no additional municipal land transfer tax is levied, resulting in total estimated land transfer taxes of $38,975.
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Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.
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