362 Winston Road

1020 - WO West, Oakville, L6L 4W5

$1,974,000

Reduced $126,000 from $2,100,000

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  • 3 bedrooms
  • 4 bathrooms
  • 8 parking
  • 2000-2500 sq ft

Listed 24 days ago · MLS® W13830254

About this home

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.

Details

Type
Detached
Style
1 1/2 Storey
Age
51-99 years
Size
2000-2500 sq ft
Lot
75.13 × 155.94 ft
Basement
Crawl Space, Full, Unfinished, Finished
Garage
Attached
Kitchens
1
Property tax
$9,004 (2026)
Neighbourhood
1020 - WO West
Municipality
Oakville
Price per sq ft
$877 (about the same as detached houses in 1020 - WO West)

Interior

Bedrooms
3 above ground
Bathrooms
1 × 4-piece (main), 1 × 3-piece (ground), 1 × 5-piece (second), 1 × 3-piece (basement)
Rooms
11 above ground
Family room or den
Yes
Fireplace
Natural Gas
Features
Central Vacuum, Water Heater Owned, Auto Garage Door Remote

Heating, cooling and services

Heating
Forced Air, Gas
Air conditioning
Central Air
Water and sewer
Sewer

Building and exterior

Style
1 1/2 Storey
Exterior
Stucco (Plaster)
Roof
Asphalt Shingle
Foundation
Concrete Block
Age
51-99 years
Faces
West

Parking

Garage spaces
4
Total parking
8
Driveway and parking
Private, Private Double

Lot

Size
75.13 × 155.94 ft

More

Possession
Flexible
Cross street
Rebecca/Fourth Line

Rooms

RoomLevelSizeFeatures
Living RoomMain4.67 × 2.99 m (15'4" × 9'10")
Dining RoomMain4.96 × 2.33 m (16'3" × 7'8")
KitchenMain3.56 × 2.94 m (11'8" × 9'8")
BreakfastMain3.66 × 2.66 m (12' × 8'9")
Bedroom 2Main4.13 × 3.44 m (13'7" × 11'3")
Bedroom 3Main4.15 × 2.74 m (13'7" × 9')
BathroomMain1.99 × 1.51 m (6'6" × 4'11")4 Pc Bath
OtherMain2.72 × 1.25 m (8'11" × 4'1")
Family RoomGround5.29 × 4.76 m (17'4" × 15'7")
BathroomGround3.25 × 1.55 m (10'8" × 5'1")3 Pc Bath
Primary BedroomSecond6.43 × 5.89 m (21'1" × 19'4")
BathroomSecond3.38 × 1.52 m (11'1" × 5')5 Pc Ensuite
LaundryBasement8.21 × 2.45 m (26'11" × 8')
BathroomBasement1.98 × 1.85 m (6'6" × 6'1")3 Pc Bath
RecreationBasement4.42 × 3.26 m (14'6" × 10'8")
DenBasement4.53 × 3.26 m (14'10" × 10'8")
OfficeBasement3.53 × 3.26 m (11'7" × 10'8")

Location

Location is approximate. See nearby homes on the map

Recent sales nearby

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The neighbourhood

Getting around Car-dependent

  • 🚆 Bronte GO2.3 km

Within a 10-minute walk: no grocery stores, 0 cafés and restaurants, 5 parks. Nearest park: Spring Garden Park (400 m).

Schools nearby

Elementary

  • St. Nicholas Catholic Elementary School Catholic
    EQAO: Gr 6 reading 96%, math 70%
    10 min walk
  • Brookdale Public School
    EQAO: Gr 6 reading 96%, math 48%
    11 min walk
  • Pine Grove Public School
    EQAO: Gr 6 reading 96%, math 60%
    12 min walk
  • École élémentaire Patricia-Picknell French
    EQAO: Gr 6 reading 81%, math 75%
    13 min walk

Secondary

  • Thomas A. Blakelock High School
    EQAO: Gr 9 math 79%, literacy test 90%
    8 min walk
  • St. Thomas Aquinas Catholic Secondary School Catholic
    EQAO: Gr 9 math 72%, literacy test 89%
    1.7 km

EQAO: share of students meeting the provincial standard (2024–25). Ontario average: Gr 6 reading 86%, math 51%; Gr 9 math 55%; literacy test 83%.

Closest schools, not school zones. Check which school serves this address with the school board before relying on it.

Who lives here postal area L6L

Owners / renters
79% / 21%
Median household income
$122,000
Average age
45
Children under 15
15%
Homes
67% detached, 18% high-rise
Commute by transit
6%
Population
30,012

Languages spoken most at home besides English: Mandarin 2.4%, Arabic 1.4%, Spanish 0.8%, Tagalog (Pilipino, Filipino) 0.8%.

Safety

Crime Severity Index for Halton Region (Oakville/Burlington) police: 31 vs 57 for Ontario (2025).

Police-reported figures for the whole police service area, not this street. Rates use the area’s resident population.

Distances are approximate. Places © OpenStreetMap contributors. Neighbourhood figures: Statistics Canada, 2021 Census. School results: EQAO via Ontario Data Catalogue (Open Government Licence – Ontario). Crime Severity Index: Statistics Canada.

Living here

Commute

To downtown Hamilton: 23 km. Transit times · Driving times

Noise Nothing major nearby

No highway within 500 m, rail line within 300 m, or airport flight path nearby.

Distances from the map, not noise measurements. Visit at rush hour to judge for yourself.

Internet High-speed

50/10 Mbps or faster available here by cable, fibre or DSL (the federal high-speed target).

From the federal broadband map. Check exact speeds and providers for the address.

Roads, rail, airports and planned stations © OpenStreetMap contributors. Internet: Innovation, Science and Economic Development Canada, National Broadband Data.

Listed by Royal LePage Realty Plus Oakville, Brokerage.

Listing information provided by PropTx Innovations Inc. and TRREB; deemed reliable but not guaranteed accurate by PropTx.

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