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43.73° N · 79.40° W — Toronto & nearby · 9,720 homes for sale today43.73° N · 79.40° W — 9,720 homes today(647) 554-7436Saved

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

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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 StartDate EndList PricePriceEventListing ID
Date StartN/AN/A$1,799,900N/AFor SaleW14117948

Inside

Room by room

From the listing.

Main8 rooms
  • 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
Ground2 rooms
  • Family4.76 × 5.29 m
  • Bathroom1.54 × 3.25 m3 Pc Bath
2nd2 rooms
  • Primary5.89 × 6.43 m
  • Bathroom1.52 × 3.37 m5 Pc Ensuite
Bsmt5 rooms
  • 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

StationLinesDistance
Bronte GOGO Transit train: Lakeshore West2.3 km
Oakville GOGO Transit train: Lakeshore West3.7 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

Middle half: $1.39M to $3.2M

New in 7 days
4

32 in 28 days

Price cuts
19%

18 listings

This home is asking 10% below the median.

See all homes in West

Asking 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.

Lot

Lot area
11,716 sq ft1,088 m²
Street frontage
75.13 ft22.9 m
Depth
155.94 ft47.5 m
75.13 × 155.94 ftWINSTON RD

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.

Price$1,799,900

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 Ahmad

Shemeer AhmadVALERY REAL ESTATE INC.

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(647) 554-7436

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