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Photo of 362 WINSTON ROADFor sale26 photos
Photo of 362 WINSTON ROAD
Photo of 362 WINSTON ROAD
Photo of 362 WINSTON ROAD
Photo of 362 WINSTON ROAD
Photo of 362 WINSTON ROAD
Photo of 362 WINSTON ROAD

For sale

362 Winston Road

362 WINSTON ROAD

MLS® W14117948 · 0 days on market · Active

$1,799,900

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About this property

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. (id:67193)

Beds
3
Baths
4

Features & Amenities

Interior

Total bedrooms
3
Total bathrooms
4
Parking
8

Area & Lot

Status
For sale
MLS® ID
W14117948
Type
House
Ownership
Freehold
Lot size
75.1 x 155.9 FT
Neighbourhood
1020 - WO West

Financial

Sale price
$1,799,900
Property taxes
$9,004 (2025)

Rooms

RoomLevelDimensions
Living roomMain level4.67 x 2.99
Primary BedroomSecond level6.43 x 5.89
BathroomSecond level3.37 x 1.52
Dining roomMain level4.96 x 2.33
Laundry roomBasement8.21 x 2.45
BathroomBasement1.98 x 1.85
Recreational, Games roomBasement4.42 x 3.26
DenBasement4.53 x 3.26
OfficeBasement3.53 x 3.26
KitchenMain level3.56 x 2.94
Eating areaMain level3.66 x 2.66
Bedroom 2Main level4.13 x 3.44
Bedroom 3Main level4.15 x 2.74
BathroomMain level1.99 x 1.51
OtherMain level2.72 x 1.25
Family roomGround level5.29 x 4.76
BathroomGround level3.25 x 1.54

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Monthly payment

$8,163

Principal borrowed
$1,439,920
Total interest over amortization
$1,008,921
CMHC insurance premium
Not required
Down payment
$359,980 (20.0%)
Principal Interest

Not included

Property tax, condo maintenance fees and home insurance are paid separately and are not part of this payment. Budget for them alongside it.

CMHC premium schedule as of 2026-08-18. Estimate only — not financial advice. Actual payments, insurance premiums and approval depend on your lender.

Land Transfer Tax — pre-filled with this price.

Neighbourhoods

Oakville

A lakeshore town in Halton Region with a walkable downtown, harbour, and mature residential streets.

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Listed by Royal LePage Realty Plus Oakville, Brokerage. The information contained on this site is based in whole or in part on information that is provided by members of The Canadian Real Estate Association, who are responsible for its accuracy. CREA reproduces and distributes this information as a service for its members and assumes no responsibility for its accuracy.

View this listing on REALTOR.ca®

This website is operated by a brokerage or salesperson who is a member of The Canadian Real Estate Association.

Kerrland Realty Group

Strategic Guidance. Personalized Service. Proven Results

Kerrland Realty Group is committed to delivering a seamless and elevated real estate experience through local expertise, skilled negotiation, and tailored strategies designed around each client's unique goals.

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