The trademarks MLS®, Multiple Listing Service®, and the associated logos are owned by the Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). Data is deemed reliable but not guaranteed.
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.
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Age Groups
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Owners vs Renters
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What’s NearbyDistances approximate
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Transit score information is not available for this listing.
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Estimated Rental Income
Rental estimate coming soon
We’re not showing a number until we have a data source we trust. When it’s connected, this section will show:
A monthly rent range from nearby leased homes of the same type and size
The leased comparables behind it (signed-in, VOW-gated)
Gross yield at the current list price
Monthly Cost
A quick estimate to plan with. Taxes come from the listing; change the other inputs to match your situation.
Estimated monthly$7,484/mo
Mortgage (principal + interest)$6,733
Property taxFrom listing: $9,004/yr$750
Minimum 20% ($359,980 on this price) applies to homes priced over $1.5M in Canada; the slider starts at 20%. Confirm with a lender.
Mortgage uses Canadian semi-annual compounding. Houses-Gate doesn’t offer financing.
Estimated Budget
About how much cash you’ll need on closing day, besides the mortgage.
Down payment20% of the list price$359,980
Ontario land transfer taxProvincial brackets, no first-time refund$32,473
Legal fees & disbursementsTypical range $1,800–$2,800$1,800
Home inspectionTypical range $500–$800$600
Title insuranceTypical range $300–$600$400
Cash needed at closingEstimate$395,253
First-time buyers can get up to $4,000 back on Ontario land transfer tax. Oakville has no municipal land transfer tax (Toronto does).
Uses Ontario’s land transfer tax brackets and the down payment set in Monthly Cost. Legal, inspection and title-insurance figures are typical ranges, not quotes.
Listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The data is deemed reliable but is not guaranteed to be accurate. The trademarks MLS®, Multiple Listing Service®, and the associated logos are owned by the Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
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.
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither listing broker(s) nor HousesGate shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless.
