362 Winston Road, Oakville, ON L6L 4W5
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.
Living Room
4.67 x 2.99 m
Main
Dining Room
4.96 x 2.33 m
Main
Kitchen
3.56 x 2.94 m
Main
Breakfast
3.66 x 2.66 m
Main
Bedroom 2
4.13 x 3.44 m
Main
Bedroom 3
4.15 x 2.74 m
Main
Bathroom
4 Pc Bath
1.99 x 1.51 m
Main
Other
2.72 x 1.25 m
Main
Family Room
5.29 x 4.76 m
Ground
Bathroom
3 Pc Bath
3.25 x 1.55 m
Ground
Primary Bedroom
6.43 x 5.89 m
Second
Bathroom
5 Pc Ensuite
3.38 x 1.52 m
Second
Laundry
8.21 x 2.45 m
Basement
Bathroom
3 Pc Bath
1.98 x 1.85 m
Basement
Recreation
4.42 x 3.26 m
Basement
Den
4.53 x 3.26 m
Basement
Office
3.53 x 3.26 m
Basement
Interior features
Central Vacuum, Water Heater Owned, Auto Garage Door Remote
Basement
Crawl Space, Full, Unfinished, Finished
Bathrooms
1 × 4-piece — Main, 1 × 3-piece — Ground, 1 × 5-piece — Second, 1 × 3-piece — Basement
Fireplace
Yes
Family room
Yes
Kitchens
1
Rooms (above / below grade)
11 above, 0 below
Approximate age
51-99
Architectural style
1 1/2 Storey
Construction materials
Stucco (Plaster)
Foundation
Concrete Block
Roof
Asphalt Shingle
Direction faces
West
Garage type
Attached
Garage spaces
4
Total parking spaces
8
Driveway parking
4
Parking features
Private, Private Double
Lot size
75.13 x 155.94 ft
Cross street
Rebecca/Fourth Line
Directions
Rebecca/Maplehurst/Winston Rd
Neighbourhood
1020 - WO West
Heating
Forced Air — Gas
Cooling
Central Air
Water
Sewer
Sewer
List price
$1,974,000
Original list price
Annual taxes
$9,004
Tax year
2026
Assessed value
$1,042,000
Assessment year
2025
Legal description
LT 23, PL 579 ; S/T TW31604 OAKVILLE
Inclusions
Exclusions
MLS #
W13830254
Status
Active
Transaction type
For Sale
Property type
Residential Freehold
Property sub type
Detached
Days on market
List date
Possession
Flexible
Occupancy
Owner
Listing brokerage
Royal LePage Realty Plus Oakville, Brokerage
$1,624,450
Median list price
40
Active listings
New in last 30 days
Median days on market
Estimated monthly payment
$9,463
Educational estimate only — actual payment depends on your lender, credit, and insurance requirements.
Sign in to see recent sold prices for homes like this one nearby.

$1,999,900
392 Fourth Line, Oakville, ON L6L 5A4
SOURCE 4 REALTY INC.

$1,899,000
446 Willis Drive, Oakville, ON L6L 4V5
RE/MAX REAL ESTATE CENTRE INC.

$1,649,900
583 Stephens Crescent, Oakville, ON L6K 1Y2
ONE PERCENT REALTY LTD.

$1,599,000
384 Ashbury Road, Oakville, ON L6K 2M7
GLOBAL BRICKS EXECUTIVE HOMES REALTY

$1,598,000
491 Tipperton Crescent, Oakville, ON L6L 5E1
EXP REALTY

$1,590,000
412 Sandmere Place, Oakville, ON L6L 4G4
MASTER`S TRUST REALTY INC.