362 Winston Road, Oakville, ON

Oakville, 1020 - WO West Hood
Rebecca/Fourth Line
3 Br | 4 Bath | 2000-2500 Sqft
$2,100,000 For Sale

Property Overview

  • Detached — 1 1/2 Storey
  • SqFt: | 2000-2500 Sqft
  • Lot Size: 75.13 x 155.94 Feet
  • Age: 51-99 Years
  • Basement: Crawl Space, Full, Unfinished, Finished
  • Exterior: Stucco (Plaster)
  • Taxes: 9,004 / 2026
  • Zoning: n/a
  • MLS #: W13830254
  • Sewer: Sewer
  • Heat Source: Gas , Forced Air

Property Description

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.

All window coverings, electrical light fixtures, washing machine and dryer, upright freezer in basement, bar fridge, central vac & attachments, Maytag oven, dishwasher, Kitchenaid fridge, over the range hood, on the counter microwave, alarm system (owned), bathroom mirrors, Hot water heater (owned), GDO + remotes.

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 1 1/2 Storey
  • Lot: 75.13 x 155.94 Feet
  • Region: Halton
  • Hood: 1020 - WO West
  • Zoning: n/a
  • Lot Irreg: Fronting on: West
  • Fronting On: West

Building Details

  • Age: 51-99 Years
  • Exterior: Stucco (Plaster)
  • Heat: Gas , Forced Air
  • A/C: Central Air
  • Interior Features: Central Vacuum, Water Heater Owned, Auto Garage Door Remote
  • Pool: None
  • Sewer: Sewer
  • Garage: Attached
  • Total Parking: 8.00
  • Driveway: Private, Private Double

Property Interior

  • Sqft: 2000-2500 Sqft
  • Bed: 3
  • Bath: 4
  • Kitchen: 1
  • Family Room: No
  • Basement: Crawl Space, Full, Unfinished, Finished
Rooms Details

Living Room

Main Level

4.67 x 2.99

Dining Room

Main Level

4.96 x 2.33

Kitchen

Main Level

3.56 x 2.94

Breakfast

Main Level

3.66 x 2.66

Bedroom 2

Main Level

4.13 x 3.44

Bedroom 3

Main Level

4.15 x 2.74

Bathroom

Main Level

1.99 x 1.51

4 Pc Bath

Other

Main Level

2.72 x 1.25

Family Room

Ground Level

5.29 x 4.76

Bathroom

Ground Level

3.25 x 1.55

3 Pc Bath

Primary Bedroom

Second Level

6.43 x 5.89

Bathroom

Second Level

3.38 x 1.52

5 Pc Ensuite

Laundry

Basement Level

8.21 x 2.45

Bathroom

Basement Level

1.98 x 1.85

3 Pc Bath

Recreation

Basement Level

4.42 x 3.26

Den

Basement Level

4.53 x 3.26

Office

Basement Level

3.53 x 3.26

Property Listed by: Royal LePage Realty Plus Oakville, Brokerage
Virtual Tour: https://unbranded.youriguide.com/362_winston_rd_oakville_on/

Home Valuation Estimate

What is 362 Winston Road, Oakville, ON worth in today’s 1020 - WO West, Oakville market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 3-bedroom Detached with 2000-2500 sq. ft. in 1020 - WO West, Oakville. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 362 Winston Road
  • Neighborhood: 1020 - WO West
  • Zip/Postal Code: L6L 4W5
  • Nearby Amenities:
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About 362 Winston Road, Oakville, ON L6L 4W5, Oakville

Located at 362 Winston Road, Oakville, ON in Oakville (1020 - WO West neighbourhood), near Rebecca/Fourth Line. This freehold home offers Detached, ["1 1\/2 Storey"], 3 bedrooms, 4 bathrooms and 2000-2500 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Crawl Space, Full, Unfinished, Finished • 8 parking spots • Garage: Attached • Heating: Gas Forced Air • Cooling: Central Air. Property taxes are approximately $9,004 for 2026. 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.

FAQs for 362 Winston Road, Oakville, ON , 1020 - WO West , Oakville

What are the listing details for 362 Winston Road, Oakville, ON?
362 Winston Road, Oakville, ON is a Detached for sale in Oakville, in the 1020 - WO West neighbourhood, Halton. The current list price is $2,100,000. MLS number: W13830254.
How many bedrooms and bathrooms does this home have?
362 Winston Road, Oakville, ON is listed as a Detached with a ["1 1\/2 Storey"] style, featuring 3 bedroom(s) and 4 bathroom(s). The listed interior size range is 2000-2500 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 75.13 x 155.94 Feet. The basement is listed as: Crawl Space, Full, Unfinished, Finished. Garage type: Attached. Total parking: 8 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Forced Air. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Stucco (Plaster).
Where is this property located?
362 Winston Road, Oakville, ON is located in the 1020 - WO West neighbourhood of Oakville. The listed cross street is Rebecca/Fourth Line.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $9,004 / 2026. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.