43.4239° N · 79.6956° W — West, Oakville — MLS® #W14117948
362 Winston Rd
$1,799,900
West, Oakville, Ontario L6L 4W5
- 3
- BedroomsBeds
- 4
- BathroomsBaths
- 2000-2500 sqft2000-2500
- SizeSq ft
- 75.13 x 155.94 ft
- Lot sizeLot
Inquire about this listing
In short · from the listing record
362 Winston Rd is a 3-bedroom, 4-bathroom detached house in West, Oakville, listed for sale at an asking price of $1,799,900 (MLS® W14117948).
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.
Listing readings
How it measures up
Scores from the listing record and the market around it.
78Good
Condition score
2 documented update signals
Listing age, structured features and disclosed update language; not an inspection.
5Shortfall
Cash flow quality
−$4,962/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Median of 7 detached homes with 3 bedrooms for lease in West right now. Cost of owning counts the mortgage and property tax.
Condition uses listing-record signals, not an inspection.
The data table
Every fact
Everything the board publishes for this home.
- Tax
- $9,004 / 2026
- MLS® number
- W14117948
- Board
- TRREB MLS®
- Property Type
- Detached
- Building Age
- 51-99
- Time on market
- Size
- 2000-2500 sqft
- Lot Size
- 75.13 x 155.94 ft
- Listed on
- Parking
- 4 Attached, 8 Parking
Listing history
Listing activity for 362 Winston Rd, Oakville, Ontario
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $1,799,900 | N/A | For Sale | W14117948 |
Inside
Room by room
From the listing.
- Living2.99 × 4.67 m
- Dining2.33 × 4.96 m
- Kitchen2.94 × 3.56 m
- Breakfast2.66 × 3.66 m
- 2nd Br3.44 × 4.13 m
- 3rd Br2.74 × 4.15 m
- Bathroom1.51 × 1.99 m4 Pc Bath
- Other1.25 × 2.72 m
- Family4.76 × 5.29 m
- Bathroom1.54 × 3.25 m3 Pc Bath
- Primary5.89 × 6.43 m
- Bathroom1.52 × 3.37 m5 Pc Ensuite
- Laundry2.45 × 8.21 m
- Bathroom1.85 × 1.98 m3 Pc Bath
- Rec3.26 × 4.42 m
- Den3.26 × 4.53 m
- Office3.26 × 3.53 m
Property
- Property Type
- Detached
- Style
- Bungalow
- Community
- West
- Municipality
- Oakville
Building
- Size
- 2000-2500 sqft
- Building Age
- 51-99
- Construction
- Stucco/Plaster
Inside
- Bedrooms
- 3
- Bathrooms
- 4
- Bathroom Details
- 1 × 4pc Main, 1 × 3pc Ground, 1 × 5pc 2nd, 1 × 3pc Bsmt
- Basement Type
- Crawl Space
- Kitchens
- 1
Parking
- Driveway
- Private, Pvt Double
- Garage Type
- Attached
- Garage
- 4
- Additional Parking
- 4
- Total Parking
- 8
Utilities
- Water
- Municipal
- Cooling
- Central Air
- Heating Type
- Forced Air
Land
- Sewer
- Sewers
- Frontage
- 75.13 ft
- Depth
- 155.94 ft
- Lot Size
- 75.13 x 155.94 ft
Where it sits
The street and the area
Asking prices on the map.
Map and tour
Transit nearby
| Station | Lines | Distance |
|---|---|---|
| Bronte GO | GO Transit train: Lakeshore West | 2.3 km |
| Oakville GO | GO Transit train: Lakeshore West | 3.7 km |
The nearest subway, light rail, train, bus rapid transit stations 5 km, as the crow flies. Source: GO Transit schedule data (GTFS) from Metrolinx under the Open Government Licence – Ontario – Metrolinx, downloaded October 18, 2026. Data used in this product or service is provided with the permission of Metrolinx. Metrolinx makes no representations or warranties of any kind, express or implied, with respect to the Data and assumes no responsibility for the accuracy or currency of the data used in this product or service. Contains information licensed under the Open Government Licence – Ontario – Metrolinx.
Around it
Detached in West
Active listings only, today.
Detached homes for sale in West right now
- For sale now
- 97
- Median asking price
- $2M
- New in 7 days
- 5
- Price cuts
- 19%
Middle half: $1.39M to $3.2M
33 in 28 days
18 listings
This home is asking 10% below the median.
See all homes in WestAsking prices and counts of the MLS® listings on this site as of today. Asking figures only, never sold or leased prices.
Site report
What the record says
What the City and the conservation authority have on file for this address.
- provincial plansNone in rangeOutside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areas
- wetlandNone in rangeNo mapped wetland within 120 m
- aggregateNone in rangeNo licensed pit or quarry within 2 km
- wellsNone in rangeNo recorded oil, gas or salt well within 250 m
- transitOn recordTransit stop within 400 m From the transit agency’s published stop map; the nearest is 270 m away. Routes and stops change; check the agency’s schedule.
- trailOn recordA trail on the Ontario trail network within 1 km
- water wellsNone in rangeNo water-supply well recorded within 250 m 1 test or monitoring hole also recorded.
- npriNone in rangeNo facility within 1 km reports pollutant releases to Environment Canada The nearest is The Regional Municipality of Halton — Oakville Southwest Wastewater Treatment Plant, 1.2 km away. Only facilities above the inventory’s reporting thresholds are listed.
- fcsiNone in rangeNo federal contaminated site within 1 km The federal inventory covers federal land only; it says nothing about provincial or private sites.
- electricityOn recordElectricity is distributed here by Oakville Hydro Electricity Distribution Inc.
- internet speedOn recordWired internet 50/10 Mbps or faster is listed at a household 60 m away Fixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (60 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.
- broadbandOn recordAcross the surrounding area: fibre to the home, cable, DSL internet listed Fibre to the home: Bell, Cogeco Connexion, Rogers. Cable: Cogeco Connexion. DSL: Bell. Fixed wireless: Bell, Rogers, SkyChoice Communications. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.
Each record is the map at the home’s location, not an inspection. Confirm anything that matters with the municipality, Conservation Halton or the record’s publisher.
Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Town of Oakville.
Lot
- Lot area
- 11,716 sq ft1,088 m²
- Street frontage
- 75.13 ft22.9 m
- Depth
- 155.94 ft47.5 m
The area is the frontage multiplied by the depth, so boundaries are approximate. Confirm with a survey before you buy.
Source: the MLS® listing record, measured by GeoWarehouse.
Land transfer tax on this home
- Ontario land transfer tax
- $32,473
- Total land transfer tax
- $32,473
- First-time buyer rebates (Ontario up to $4,000)
- −$4,000
- Total for first-time buyers
- $28,473
See how this is worked out
- 0.5% on the first $55,000
- $275
- 1.0% from $55,000 to $250,000
- $1,950
- 1.5% from $250,000 to $400,000
- $2,250
- 2.0% from $400,000 to $1,799,900
- $27,998
- Ontario total
- $32,473
An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.
Schools
Nearest schools
Straight-line distances. Check catchments with the board.
ElementaryEQAO average 2024–25
- Brookdale Public SchoolHalton DSBPublic · grades JK–878%Grade 6 average650 m
- St. Nicholas Catholic Elementary SchoolHalton CDSBCatholic · grades JK–885%Grade 6 average700 m
- Pine Grove Public SchoolHalton DSBPublic · grades 1–8 · French Immersion85%Grade 6 average800 m
- École élémentaire Patricia-PicknellConseil scolaire ViamondeFrench-language public · grades JK–679%Grade 6 average900 m
SecondaryGrade 9 math 2024–25
- Thomas A Blakelock High SchoolHalton DSBPublic · grades 9–12 · French Immersion79%Grade 9 math450 m
- St. Thomas Aquinas Catholic Secondary SchoolHalton CDSBCatholic · grades 9–1272%Grade 9 math1.8 km
- Abbey Park High SchoolHalton DSBPublic · grades 9–1289%Grade 9 math3.6 km
- École secondaire Gaétan GervaisConseil scolaire ViamondeFrench-language public · grades 9–1285%Grade 9 math4.6 km
EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.
Searches this home is in
Keep looking
The ledger
What it costs to own
Worked out for this home. Change any number.
A month, all in
$8,962
- Mortgage$8,212
- Property tax$750
A planning figure, not a quote.
Land transfer tax
$32,473
$28,473 for first-time buyers.
Rent, similar homes
$4,000
a month, median asking rent of 7 similar homes in West.
Community
Who lives around it
Similar homes
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Shemeer AhmadVALERY REAL ESTATE INC.
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