304 Winston Road, Oakville, ON

$4,298,000
MLS#:W13159190
5 beds
6 baths
3500-5000 sqft
8.0 parking
Residential Freehold
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Property Highlights

Welcome to this remarkable 2-Storey detached located in the coveted neighborhood of 1020 - WO West. Expertly crafted featuring premium brick and stone construction, this residence presents an exceptional opportunity offered at $4,298,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.

  • 5 Bedrooms and 6 Bathrooms
  • Generous living space spanning 3500-5000 sqft on a premium 77 x 163 ft lot
  • Features a full, finished basement, adding superb versatility for recreation, a home gym, or extra storage
  • 8.0 total parking spaces available with a convenient attached configuration
  • Notable attributes: Generator - Full, Primary Bedroom - Main Floor, Air Exchanger
  • equipped with central air central cooling and highly efficient forced air heating via gas

Description

Welcome to 304 Winston Rd, an exceptional custom-designed and built residence offering 5897 sq ft of total living space in one of Oakville's most prestigious neighbourhoods. Perfectly positioned on a premium lot just a few minutes walk to Appleby College, this spectacular home blends timeless transitional architecture with sophisticated finishes, modern smart-home technology, and luxurious resort-inspired living.The exceptional backyard is an outdoor retreat featuring custom infinity edge saltwater pool and hot tub surrounded by expansive entertaining areas. Enjoy indoor-outdoor living beneath the covered rear porch complete with built-in automated screens, fireplace and TV allowing for enjoyment well into the shoulder seasons. Integrated security cameras, advanced Control4 automation, and a dedicated Generator provide added convenience, comfort, and peace of mind. Inside, the home exudes warmth and sophistication. The thoughtfully designed layout offers exceptional versatility, highlighted by a rare main floor primary complete with a luxurious ensuite bath and walk-in closet. An integrated elevator provides ease with access to all levels of the home. With 4+1 bedrooms and 5.5 baths, the residence is perfectly suited for families of all sizes. Two separate laundry rooms further enhance the home's everyday practicality and convenience. The fully finished lower level has been meticulously designed for year-round enjoyment featuring radiant heated floors throughout for exceptional comfort. This impressive space includes a home theatre, gym, rec area, guest/nanny suite & ample storage. Combining luxurious amenities, timeless design, and an unbeatable South Oakville location close to top-ranked schools, parks, waterfront trails, and everyday conveniences, 304 Winston Rd. presents an extraordinary opportunity to experience refined custom living in one of the town's most sought-after communities.

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Key Features

Bedrooms
5
Bathrooms
6
Kitchens
1
Living Area
3500-5000 sqft
Property Type
Residential Freehold

Additional Details

StatusPrice Change
Listed Date5/21/2026
Transaction TypeFor Sale

Property Details

Property Sub-TypeDetached
Architectural Style2-Storey
ConstructionBrick, Stone
BasementFull, Finished
Lot Size77 × 163 Feet
CountyHalton
Annual Tax$17,126.65
Legal DescriptionLT 12, PL 579 ; S/T TW31604 OAKVILLE

Parking & Garage

Parking Spaces8.0
Garage Spaces6
Garage TypeAttached

Heating & Cooling

Heat SourceGas
Heat TypeForced Air
CoolingCentral Air

Features

Property Features

School, Park, Lake/Pond

Interior Features

Generator - Full, Primary Bedroom - Main Floor, Air Exchanger, Central Vacuum, Auto Garage Door Remote, Water Heater Owned, Sump Pump, ERV/HRV, Bar Fridge

Security Features

Carbon Monoxide Detectors, Security System

Community Features

Location

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304 Winston Road, Oakville, ON
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Property History

No historical data available for this property.

This could be the first listing for this address.

Pricing & Value Insights

Data-driven valuation for 304 Winston Road, Oakville, ON L6L 4W5

Estimated Sales Range
$1.2M - $1.4M

Based on 0 recent similar sales in the pocket.

Market Speed
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Mortgage & Affordability Audit

Calculate your monthly payment, minimum downpayment, and land transfer taxes for this home in Oakville.

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Interest Rate5.25%
Down Payment$859,600 (20.0%)
* Minimum Canadian down payment required for this price is $859,600.
Amortization Period25 Years
Estimated Monthly Payment$20,490Based on a loan of $3,438,400 over 25 years.
Purchase Price$4,298,000
Loan Amount$3,438,400
Provincial Land Transfer Tax:$93,925
Total Estimated Closing Taxes:$93,925

About Purchasing a Home in Oakville, ON

For a property listed at $4,298,000 in Oakville, the legal minimum down payment is $859,600 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.

Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $93,925 for this transaction. As this listing is in Oakville (outside the City of Toronto), no additional municipal land transfer tax is levied, resulting in total estimated land transfer taxes of $93,925.

Nearby Listings

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No current listings found in Oakville.

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City & Neighborhood Guide

Comprehensive city-wide demographics, local real estate stats, and school rankings for Oakville.

Verified Local Data
City Population213,759
City Median Age41.5 Yrs
City Ownership82% Owners
Avg Area List Price$2,501,959

People & Families

Age Distribution

Household Composition

One-person households
18%
Families with children
52%
Couples without children
26%
Other households
4%

Top Ethnic Origins

English22%
Canadian16%
Scottish16%
Irish15%

Local Schools Guide

Elementary Schools

Sunningdale
PublicOakville, Ontario, L6H 1T4
8.8
Abbey Lane
Public1160 Old Abbey Lane, Oakville, Ontario, L6M 1S4
7.5
River Oaks
Public2173 Munn's Avenue, Oakville, Ontario, L6H 3S9
6.4
Forest Trail
PublicForest Trail Place, Oakville, Ontario, L6M 2G3
10.0
West Oak
Public2071 Fourth Line, Oakville, Ontario, L6M 3K1
6.6

Secondary Schools

White Oaks
PublicOnslow Court, Oakville, Ontario, L6H 1H9
8.8
Gaétan Gervais
Public1075 McCraney Street East, Oakville, Ontario, L6H 1H9
9.3
St. Ignatius of Loyola
Catholic1550 Nottinghill Gate, Oakville, Ontario, L6M 1X7
8.1
Holy Trinity
Public2420 Sixth Line, Oakville, Ontario, L6H 5Z8
7.1
Abbey Park
Public1455 Glen Abbey Gate, Oakville, Ontario, L6M 2G5
9.3

Homes & Housing

Structural Home Types

Tenure (Ownership vs Rental)

Owner-Occupied82%
Rented18%

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Notice: Market Insights are generated by analyzing real-time data and should be used for informational purposes only. Consult with a licensed professional for exact valuations.

Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.