For sale

This one's priced above recent comparable sales, and new this week. Here's everything I've got — ask me anything about it.

Oakville · Halton Region · West

362 Winston Road

Detached

MLS® #W14117948

Listed for$1,799,9002 days on market

3 bed 4 bath 8 parking 2000-2500 sq ft~$800/sq ft

New this week
6 schools within 1 km
Transit stop ~260 m

Free · about 10 seconds

Is $1,799,900 a fair price?

Our read: it’s priced above recent comparable sales — based on 68 sales nearby. Sign in free to see exactly how far above it is, plus the full range comparable homes sold in.

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Measured against 68 recent comparable sales nearby — sign in free to see the range they sold in (boards require a verified email · VOW rules).

Est. all-in monthly~$9,125/momortgage + property tax + maintenance · 20% down · example rate (compounded semi-annually) — the math on the list price, not a quote or what you can afford. For real rates, Alex can connect you with a mortgage pro.

On the map

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This home below comps above in lineOpen full map →

6 schools within ~1 km · nearest transit stop ~0.26 km

Property information

What house buyers ask first

Lot size: 75.13 × 155.94 ft
Square footage: 2000-2500 sq ft
Age: ~51-99 years old
Property tax: $9,004 / yr
Parking: 8 spaces · Attached
Basement: Crawl Space, Full, Unfinished, Finished

Property summary

Property type: Detached
Style: Bungalow
Approx. age: 51-99 years
Lot size: 75.13 × 155.94 ft
Parking: 8 spaces · Attached
Heating: Forced Air
Air conditioning: Central Air
Basement: Crawl Space, Full, Unfinished, Finished
Kitchens: 1
Exterior: Stucco (Plaster)
Property tax: $9,004 / yr
MLS®: W14117948

Room dimensions

Bedroom 2

Main4.13 × 3.44 m

Bathroom3 Pc Bath

Ground3.25 × 1.54 m

Bathroom4 Pc Bath

Main1.99 × 1.51 m

Dining Room

Main4.96 × 2.33 m

Recreation

Basement4.42 × 3.26 m

Bathroom5 Pc Ensuite

Second3.37 × 1.52 m

Laundry

Basement8.21 × 2.45 m

Breakfast

Main3.66 × 2.66 m

Family Room

Ground5.29 × 4.76 m

Kitchen

Main3.56 × 2.94 m

Bathroom3 Pc Bath

Basement1.98 × 1.85 m

Primary Bedroom

Second6.43 × 5.89 m

Office

Basement3.53 × 3.26 m

Bedroom 3

Main4.15 × 2.74 m

Living Room

Main4.67 × 2.99 m

Den

Basement4.53 × 3.26 m

Other

Main2.72 × 1.25 m

As stated by the MLS®, nothing inferred.

Nearby homes for sale

Below-comps first · all nearby homes shown, not just the good-value ones.

Detached

$1,499,000

Below recent sales

1094 Rebecca Street

4+2 bed · 5 bath·2500-3000 sq ft·6 parking

Oakville · Halton Region

Listed 7 days ago · RE/MAX Escarpment Realty Inc.

Detached

$1,049,000

Below recent sales

615 Parkside Drive

3+2 bed · 2 bath·1100-1500 sq ft·7 parking

Oakville · Halton Region

Listed 5 days ago · Bay Street Group Inc.

Listing states: renovated

Detached

$2,295,000

Above recent sales

383 Maplehurst Avenue

3+1 bed · 3 bath·1100-1500 sq ft·5 parking

Oakville · Halton Region

Listed 5 days ago · Royal LePage Signature Realty

Detached

$6,199,000

Above recent sales

368 Fourth Line

4+1 bed · 6 bath·3500-5000 sq ft·12 parking

Oakville · Halton Region

Listed 8 days ago · Royal LePage Burloak Real Estate Services

Detached

$1,999,900

Above recent sales

392 Fourth Line

2 bed · 1 bath·700-1100 sq ft·7 parking

Oakville · Halton Region

Listed 12 days ago · Source 4 Realty Inc.

Detached

$3,275,000

Above recent sales

471 Willis Drive

4+2 bed · 5 bath·3500-5000 sq ft·8 parking

Oakville · Halton Region

Listed 12 days ago · Homelife/Miracle Realty Ltd

The numbers that matter

Property tax: $9,004/yr
Est. all-in: ~$9,125/mo

Nearby rental listings are facts. Whether it works as a rental is a chat with Alex — not a number I’ll put on it.

Schools

Schools near this home, closest first by straight-line distance. These are factual locations — AskEmma doesn’t rate or rank schools.

Thomas A Blakelock High SchoolPublic · Secondary · Halton DSB0.5 km
Brookdale Public SchoolPublic · Elementary & Secondary · Halton DSB0.7 km
St. Nicholas Catholic Elementary SchoolCatholic · Elementary & Secondary · Halton CDSB0.7 km
Appleby CollegePrivate · Elementary & Secondary · ..0.7 km
Pine Grove Public SchoolPublic · Elementary & Secondary · Halton DSB0.8 km
École élémentaire Patricia-PicknellPublic · Elementary · French · CS Viamonde0.9 km

Locations: Open Database of Educational Facilities (ODEF), Statistics Canada v2.1 (2022) · Open Government Licence – Canada. School locations as of 2022 — confirm current catchment and enrolment with the school board. For official provincial results, check EQAO.

Getting around

Public transit near this home, by straight-line distance. Factual locations from OpenStreetMap — not walking time, and not a rating.

Bus stopNearest transit · Bus stop~260 m
BronteNearest GO / rail · GO / regional rail~2.3 km

Locations: OpenStreetMap public-transit stops, © OpenStreetMap contributors · Open Database Licence (ODbL). Stop locations from OpenStreetMap — confirm current routes and service with the transit agency.

Community — Oakville

$1.3MMedian sold

34Median days on market

96.1%Sale-to-list

Median sold price · Oakville1-yr +9% · 3-yr —

Source: TRREB sold data via Repliers · all property types

Neighbourhood demographics — Oakville

213,759Population (2021)

41.6Median age

$128,000Median household income

77.5%Home owners

22.5%Renters

2.9Avg household size

Source: Statistics Canada, 2021 Census

Description & details

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.

The data only goes so far — condition, light and layout are worth seeing in person, with a home inspection, before you commit.

Listed by Royal LePage Realty Plus Oakville, Brokerage. Showings via AskEmma by Alex Goodman, Sales Representative, RE/MAX Your Community Realty, Brokerage.