Listed by Royal LePage Realty Plus Oakville, Brokerage
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.
Key Facts:
Tax:
$9,004 / 2026
Property Type:
Detached
Building Age:
51-99 years
Sq. ft. size
2000-2500 sq. ft.
Lot Size:
75.13 x 155.94 feet
Lot Irregularities:
LT 23, PL 579 ; S/T TW31604 OAKVILLE
Parking:
Attached garage (4), 8 spaces in total
Basement:
Crawl Space, Full
Listing #:
W14117948
Days on Site:
8 days
Status Change:
8 days ago
Added to CiRealty:
2026-10-26
Updated on:
2026-10-26
Market Demand:
Buyer’s Market
Balanced
Seller’s Market
Property Details
Property details for 362 Winston Rd, Oakville. Listed for $1,799,900 on 2026-10-26
Property
Property Type:
Detached
Style:
Bungalow
Community:
West
Municipality:
1020
Inside
Bedrooms:
3
Bathrooms:
4
Bathrooms Detail:
1 × 4pc, main floor
Bathrooms Detail:
1 × 3pc, ground floor
Bathrooms Detail:
1 × 5pc, 2nd floor
Bathrooms Detail:
1 × 3pc, basement
Kitchens:
1
Rooms:
11
Family Room:
Yes
Den:
Yes
Fireplace:
Yes
Central Vac:
Yes
Utilities
Water:
Municipal
Cooling:
Central Air
Heating Type:
Forced Air
Building
Size:
2000-2500 sq. ft.
Building Age:
51-99 years
Construction:
Stucco/Plaster
Parking
Garage Type:
Attached
Garage Spaces:
4
Driveway:
Private, Pvt Double
Driveway Spaces:
4
Total Parking Spaces:
8
Land
Sewer:
Sewers
Frontage:
75.13 feet
Depth:
155.94 feet
Cross Street:
Rebecca/Fourth Line
Property
Property Type:
Detached
Style:
Bungalow
Community:
West
Municipality:
1020
Building
Size:
2000-2500 sq. ft.
Building Age:
51-99 years
Construction:
Stucco/Plaster
Parking
Garage Type:
Attached
Garage Spaces:
4
Driveway:
Private, Pvt Double
Driveway Spaces:
4
Total Parking Spaces:
8
Inside
Bedrooms:
3
Bathrooms:
4
Bathrooms Detail:
1 × 4pc, main floor
Bathrooms Detail:
1 × 3pc, ground floor
Bathrooms Detail:
1 × 5pc, 2nd floor
Bathrooms Detail:
1 × 3pc, basement
Kitchens:
1
Rooms:
11
Family Room:
Yes
Den:
Yes
Fireplace:
Yes
Central Vac:
Yes
Land
Sewer:
Sewers
Frontage:
75.13 feet
Depth:
155.94 feet
Cross Street:
Rebecca/Fourth Line
Utilities
Water:
Municipal
Cooling:
Central Air
Heating Type:
Forced Air
Rooms
Room details for 362 Winston Rd, Oakville. (Listed for $1,799,900 on 2026-10-26)
Living (15'4" x 9'10")
Dining (16'3" x 7'8")
Kitchen (11'8" x 9'8")
Breakfast (12'0" x 8'9")
2nd Br (13'7" x 11'3")
3rd Br (13'7" x 9'0")
Bathroom (6'6" x 4'11")
4 Pc Bath
Other (8'11" x 4'1")
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