362 Winston Road, Oakville

$1,974,000
362 Winston Road

$1,974,000

Price Change
28d
Detached1 1/2 Storey

362 Winston Road, Oakville

Total Monthly Obligation $9,088

Beds
3
Baths
4
Park
4
Sqft
2000-2500
DOM
28d
Score
15
Yield
3.1%
Cash on Cash
-9.8%
Cap Rate
2.5%
5Y IRR
7.9%
10Y IRR
8.6%
Property Type-Detached
MLS® Number-W13830254
Beds-3
Bathrooms-4
Size-2000-2500 sqft
Lot Size-75.13 × 155.94 ft
Listed on site-Sep 25, 2026
Style-1 1/2 Storey
Building Type-Detached
Age-51-99
Taxes-$9,003.51 (2026)
Parking-8 - Attached
Basement-Crawl Space, Full, Unfinished, Finished
Heating-Forced Air (Gas)
Brokerage-Royal LePage Realty Plus Oakville, Brokerage
Cooling-Central Air
Laundry-No
Fireplace-Natural Gas
Pool-None
Facing-West
Exterior-Stucco (Plaster)
Roof-Asphalt Shingle
Foundation-Concrete Block
Sewer-Sewer
Possession-Flexible
Neighbourhood-1020 - WO West
Title-Residential Freehold

No agent assigned

Welcome to 362 Winston Road, an exceptional South Oakville residence situated on one of the area's most prestigious and highly sought-after streets, surrounded by stunning custom-built multi-million-dollar homes. Just a short walk to the renowned Appleby College, this beautifully renovated bungalow offers an outstanding blend of elegance, comfort, and convenience. Thoughtfully updated and impeccably maintained, the home features a substantial rear addition showcasing a spacious family room with a cozy gas fireplace and a walkout to the private west-facing backyard. Large windows adorned with solid wood California shutters fill the home with natural light, while hardwood flooring throughout the main level adds warmth and timeless appeal. The updated kitchen overlooks the mature backyard and features a skylight that floods the space with sun. Adjacent to the kitchen, a charming breakfast nook with a bay window provides the perfect spot for casual dining, while a separate formal dining room offers an elegant setting for entertaining. Privately located on the upper level, the impressive primary retreat features a spacious sitting area, skylight, generous closet space, and a 5-piece ensuite. Two additional bedrooms and a 4-piece bathroom complete the main floor. The finished lower level expands the living space with a large recreation room, office, gym or potential additional bedroom, laundry area, abundant storage, and another full bathroom. With four full bathrooms throughout the home, there is plenty of room for family and guests. Outside, a rare oversized attached four-car garage and a private west-facing backyard offer exceptional outdoor enjoyment, mature landscaping, and beautiful sunset views. Ideally located close to high-ranking public and private schools, parks, transit, shopping, and major highways, this solidly built home presents a rare opportunity to own in one of South Oakville's most desirable enclaves.

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(utilities, internet...)
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Closing Costs

Mortgage Amount
$1,579,200
Land Transfer Taxes$35,955
Legal Fees (Est.)
$
Total cash required for closing$432,255

Total Monthly Obligation

$9,088/mo
Mortgage $7,963
Monthly Loss $6,993
Principal$2,095
Interest$5,867
Property Tax$750
Home Insurance$125
Variable Costs$250
Returns
Weight: 25%
Cap Rate
2.1%12
Cash-on-Cash
-12.7%0
5-Year IRR
5.6%13
10-Year IRR
7.1%
Returns Index
7.7/ 100
Growth Sentiment
Weight: 20%
%/yr
Score+50
%/yr
Score+50
%
%
Growth Index
50.0/ 100
GradeD
15/ 100
Avoid•Pass

Strategy: Buy & Hold — Weights: CFI 35% · RI 25%
RKI 20% · GI 20%

Assumptions & Inputs
$/mo
%
$
yr
%
Cash Flow
Weight: 35%
Gross Rent
$61,200/yr
NOI
$41,576/yr
Net Cash Flow
-$4,498/mo
Cash Margin
-88.2%0
Cash Flow Index
0.0/ 100
Risk Profile
Weight: 20%
DSCR
0.444
LTV Ratio
80.0%18
Vacancy Buffer
1.1 mo18
Risk Index
13.2/ 100

*This analysis is independently generated NOT provided by TREB or CREA.

Comparables

Properties near 362 Winston Road

Time

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