362 Winston Rd
West, Oakville, Ontario L6L 4W5
- Bedrooms
- 3
- Bathrooms
- 4
- Size
- 2,000–2,500sq ft
- Per sq ft
- $800at the range’s middle
- Lot
- 75.13 x 155.94 ft
- Tax a year
- $9,0042026 tax year
- Built
- 51-99
- Parking
- 84 attached
- Days on market
- Members
The brief
About 362 Winston Rd
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.
Insights
Condition Score
Good78/1002 documented update signals
Source: Listing age, structured features and disclosed update language; not an inspection.
Cashflow Quality
Shortfall5/100−$4,962/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Source: 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 home
Key facts
- Tax
- $9,004 / 2026
- MLS® number
- W14117948
- Board
- TRREB MLS®
- Property Type
- Detached
- Building Age
- 51-99
- Days on market
- Size
- 2000-2500 sqft
- Lot Size
- 75.13 x 155.94 ft
- Listed on
- Parking
- 4 Attached, 8 Parking
Property details
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
Additional
- Foundation
- Concrete Block
- Roof
- Asphalt Shingle
- Fireplace
- Yes
- Pool
- None
- Den
- Yes
- Family room
- Yes
- Extras
- 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, outdoor umbrella.
Rooms
| Room | Size | Features | Level |
|---|---|---|---|
| Living | 2.99 × 4.67 m | — | Main |
| Dining | 2.33 × 4.96 m | — | Main |
| Kitchen | 2.94 × 3.56 m | — | Main |
| Breakfast | 2.66 × 3.66 m | — | Main |
| 2nd Br | 3.44 × 4.13 m | — | Main |
| 3rd Br | 2.74 × 4.15 m | — | Main |
| Bathroom | 1.51 × 1.99 m | 4 Pc Bath | Main |
| Other | 1.25 × 2.72 m | — | Main |
| Family | 4.76 × 5.29 m | — | Ground |
| Bathroom | 1.54 × 3.25 m | 3 Pc Bath | Ground |
| Primary | 5.89 × 6.43 m | — | 2nd |
| Bathroom | 1.52 × 3.37 m | 5 Pc Ensuite | 2nd |
| Laundry | 2.45 × 8.21 m | — | Bsmt |
| Bathroom | 1.85 × 1.98 m | 3 Pc Bath | Bsmt |
| Rec | 3.26 × 4.42 m | — | Bsmt |
| Den | 3.26 × 4.53 m | — | Bsmt |
| Office | 3.26 × 3.53 m | — | Bsmt |
Listing history
Buy/sell history for 362 Winston Rd, Oakville, Ontario
Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $1,799,900 | N/A | For Sale | W14117948 |
Members see the full history. Prices are hidden from signed-out visitors.
The numbers
Mortgage Calculator
Plan with the current asking price
CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.
Mortgage Details
4.8% · 5-year term · 25-year amortization · 20% down
- Total down payment
- $359,980
- Total mortgage amount
- $1,439,920
- Total interest payment
- $1,023,680
- Total purchase cost
- $2,823,580
- Mortgage payment
- $8,212/mo
Cash Flow Analysis
If you rented this home out at 20% down
Break-even down payment
68%Monthly carrying cost
$8,962- Rent $4,000
- Shortfall $4,962
Rental income opens at $4,000, the median asking rent of 7 comparable homes for lease in West. Type over it with the rent you expect. This is a planning tool, not advice.
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.
Estimate
Estimated value requires sign in
Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.
The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Kassaundra Dobson, Broker of Record for a full comparative market analysis.
Comparable sales
Comparable sales require sign in
Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.
The land
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 and environment
Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.
Water and conservation2
- No mapped wetland within 120 m120 m
- No water-supply well recorded within 250 m1 test or monitoring hole also recorded.250 m
Province of Ontario open data
Planning and building activity1
- Outside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areasAt the address
Province of Ontario open data
Around the home2
- Transit stop within 400 mFrom the transit agency’s published stop map; the nearest is 270 m away. Routes and stops change; check the agency’s schedule.400 m
- A trail on the Ontario trail network within 1 km1 km
Municipal transit open data · Province of Ontario open data
Environmental records4
- No licensed pit or quarry within 2 km2 km
- No recorded oil, gas or salt well within 250 m250 m
- No facility within 1 km reports pollutant releases to Environment CanadaThe 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.1 km
- No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km
Province of Ontario open data · Government of Canada open data
Power and internet3
- Electricity is distributed here by Oakville Hydro Electricity Distribution Inc.At the address
- Wired internet 50/10 Mbps or faster is listed at a household 60 m awayFixed 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.60 m
- Across the surrounding area: fibre to the home, cable, DSL internet listedFibre 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.Area-wide
Ontario Energy Board · Innovation, Science and Economic Development Canada
Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Conservation Haltonor 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.
The market
Detached homes for sale in West right now
- For sale now
- 97
- Median asking price
- $2M
- New in 7 days
- 4
- Price cuts
- 19%
Middle half: $1.39M to $3.2M
32 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.
Market area · filters apply to the charts below
The street
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.
Schools nearby
| Elementary | Type | Distance | EQAO average 2024–25 |
|---|---|---|---|
| Brookdale Public SchoolHalton DSB | Public · grades JK–8 | 650 m | 78%Grade 6 average |
| St. Nicholas Catholic Elementary SchoolHalton CDSB | Catholic · grades JK–8 | 700 m | 85%Grade 6 average |
| Pine Grove Public SchoolHalton DSB | Public · grades 1–8 · French Immersion | 800 m | 85%Grade 6 average |
| École élémentaire Patricia-PicknellConseil scolaire Viamonde | French-language public · grades JK–6 | 900 m | 79%Grade 6 average |
| Secondary | Type | Distance | Grade 9 math 2024–25 |
|---|---|---|---|
| Thomas A Blakelock High SchoolHalton DSB | Public · grades 9–12 · French Immersion | 450 m | 79%Grade 9 math |
| St. Thomas Aquinas Catholic Secondary SchoolHalton CDSB | Catholic · grades 9–12 | 1.8 km | 72%Grade 9 math |
| Abbey Park High SchoolHalton DSB | Public · grades 9–12 | 3.6 km | 89%Grade 9 math |
| École secondaire Gaétan GervaisConseil scolaire Viamonde | French-language public · grades 9–12 | 4.6 km | 85%Grade 9 math |
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.
The verdict
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