

























362 Winston Road
1020 - WO West, Oakville
$1,799,900
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.
No extras listed.
Visit this home
Pick a time that works for you.
No upcoming open houses.
Ask our AI assistant
Schools, payments, offer timing, history — ask in plain words. This home is already in the conversation.
Listing History
Schools
Could you afford this home?
What the bank counts
This home's actual carrying costs, payment stress-tested at 6%
- Mortgage, tested at 6%
- $9,213
- Property tax
- $750
- Heat allowance
- $150
- Housing costs
- $10,113 / mo
Lenders cap these at 39% of gross income — that sets the number.
Income needed
$311,000
gross annual household income
- Payment at 4%
- $7,574 / mo
- Cash down
- $359,980
Assumes no other monthly debts · 25-yr amortization
Full affordability checkInvestment Analysis
Estimated rent, cap rate and monthly cash flow for this property
Values and trends
Nearby listings
Comparable sales
- No similar listings found.











































































































































































































































































































































































































































































































































































































































































































































































































































