$1,974,000 - 362 Winston Road, Oakville
Detached for Sale in Oakville
Popular ListingNeighbourhood: 1020 - WO West
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- MLS Number
- W13830254
- Property Type
- Detached
- Status
- active
- Days on Site
- 12
- Bedrooms
- 3
- Bathrooms
- 4
- Square Feet
- 2,000 - 2,499 sqft
- Neighbourhood
- Oakville
- Taxes (2026)
- $9,004
- Listing Brokerage
- Royal LePage Realty Plus Oakville, Brokerage
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.
Estimate your monthly payments for this property
Estimated Payment
$8,731.67/mo
5-yr fixed avg.
Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.
Discover 1020 - WO West
1020 - WO West is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.
Why Live in 1020 - WO West
- •Convenient location in Oakville
- •Access to local shops and dining
- •Good public transit connections
- •Community parks and green spaces
- •Well-maintained neighbourhoods
Nearby Schools
Transit & Commuting
- •MiWay bus routes throughout the area
- •GO Transit stations within driving distance
- •Easy highway access to 401/403/QEW
- •Walking distance to local amenities
Parks & Amenities
- •Local parks and recreational facilities
- •Community centres
- •Shopping plazas nearby
- •Restaurants and cafes
Lifestyle & Community
1020 - WO West offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.
362 Winston Road, Oakville
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Monthly Cash Flow Breakdown
Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.
Joe's Thoughts
Honest perspective from 30+ years of GTA real estate experience
Fair Market Value
At $987/sqft, this property is priced in line with current Oakville market conditions. The pricing suggests the seller has done their homework. We may have modest room for negotiation, typically 2-4% in today's market.
Detached Home Advantages
Detached homes in Oakville are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.
Starter Home Potential
3 bedrooms works well for couples planning families or small families with one child. Consider whether you might outgrow the space in 5-7 years. If so, factor in potential moving costs when making your decision. Alternatively, some buyers convert a bedroom to an office and make it work long-term.
Bathroom Count Matters
With 4 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.
Oakville Premium
Oakville commands premium prices for good reasons: top-rated schools, waterfront access, charming downtown, and affluent community. Homes here hold value exceptionally well during market corrections. The trade-off is higher property taxes and home prices. If schools and lifestyle are priorities, Oakville delivers.
About 1020 - WO West
I know 1020 - WO West well from working with many buyers and sellers here. Each pocket has its own character - let me share what I've learned about this specific street and block. During our showing, I'll point out local amenities, school catchments, and what similar homes have sold for recently.