362 Winston Road

1020 - WO West, Oakville, Ontario L6L 4W5

Overview

At a glance

Days on market0 days
ListedOct 26, 2026
UpdatedOct 26, 2026
Building age51-99 years
Size2000-2500 sq ft
Lot75.13 x 155.94 Feet
Property taxes$9,004 (2026)
Parking8 spaces
BasementCrawl Space, Full, Unfinished, Finished
MLS® numberW14117948
Data sourcePropTx MLS® System
Listing brokerageRoyal LePage Realty Plus Oakville, Brokerage

About this home

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.

Details

Property

Style
Bungalow
Building age
51-99
Fronting on
West
Cross street
Rebecca/Fourth Line
Community
1020 - WO West
Municipality
Oakville

Inside

Bedrooms above grade
3
Bathrooms
4
Kitchens
1
Basement
Crawl Space, Full, Unfinished, Finished
Family room
Yes
Fireplace
Natural Gas
Interior features
Central Vacuum, Water Heater Owned, Auto Garage Door Remote

Utilities

Heating
Forced Air
Heating fuel
Gas
Cooling
Central Air
Sewer
Sewer

Building

Construction
Stucco (Plaster)
Foundation
Concrete Block
Roof
Asphalt Shingle
Pool
None

Parking

Garage
Attached
Parking spaces
4
Total parking
8
Driveway
Private, Private Double

Land

Frontage
75.13
Depth
155.94
Lot size units
Feet
Waterfront
No
Rooms (17)
RoomLevelSizeFeatures
Living RoomMain4.67 x 2.99 Meters
Dining RoomMain4.96 x 2.33 Meters
KitchenMain3.56 x 2.94 Meters
BreakfastMain3.66 x 2.66 Meters
Bedroom 2Main4.13 x 3.44 Meters
Bedroom 3Main4.15 x 2.74 Meters
BathroomMain1.99 x 1.51 Meters4 Pc Bath
OtherMain2.72 x 1.25 Meters
Family RoomGround5.29 x 4.76 Meters
BathroomGround3.25 x 1.54 Meters3 Pc Bath
Primary BedroomSecond6.43 x 5.89 Meters
BathroomSecond3.37 x 1.52 Meters5 Pc Ensuite
LaundryBasement8.21 x 2.45 Meters
BathroomBasement1.98 x 1.85 Meters3 Pc Bath
RecreationBasement4.42 x 3.26 Meters
DenBasement4.53 x 3.26 Meters
OfficeBasement3.53 x 3.26 Meters
Value

What it’s worth

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Market read

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History

Listing history

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Neighbourhood

Around 1020 - WO West

What’s nearby

Quiet streetBackyard faces west

  • Elementary schoolSt. Nicholas Catholic Elementary Schoolabout 9 min walk
  • High schoolThomas A. Blakelock High Schoolabout 7 min walk
  • ParkSpring Garden Parkabout 5 min walk
  • Playground about 6 min walk
  • Trail about 4 min walk
  • River or lakeFourteen Mile Creekabout 4 min walk
  • Grocery storeWalmart Supercentreabout 19 min walk
  • DowntownOakvilleabout 3.5 km
  • LibraryOakville Public Library - Woodside Branchabout 11 min walk
  • Rec centre or arenaYMCAabout 16 min walk
  • Golf courseOakville Golf Clubabout 3.5 km
  • HospitalOakville Trafalgar Memorial Hospitalabout 6.3 km
  • Highway on-ramp about 27 min walk
  • GO or train stationBronteabout 33 min walk

Approximate: straight-line distances, and the backyard and street worked out from the map pin and map data © OpenStreetMap contributors. Check school boundaries with the school board.

On the map

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Community

The 1020 - WO West market

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Costs

What it would cost

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Every monthEstimate
Mortgage payment$0
Property tax$0
Monthly total$0
At closing
Ontario land transfer tax$0

Estimates only, not financial advice. Uses Canadian semi-annual compounding, the minimum down payment and mortgage insurance rules, and Ontario’s land transfer tax brackets. Your lender and lawyer confirm the real numbers. Legal fees, title insurance and moving costs aren’t included.

Listing courtesy of Royal LePage Realty Plus Oakville, Brokerage. Listing information from the PropTx MLS® System. Each listing shows the brokerage that represents it. 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. Information is deemed reliable but is not guaranteed accurate by PropTx. Last updated October 26, 2026 at 10:38 p.m.

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