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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Added:May 21, 2026(100 days ago)
Updated:Jun 18, 2026(72 days ago)
Last Checked:8 minutes ago

Property Highlights

Welcome to this remarkable 2-Storey detached located in the coveted neighborhood of 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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Property Summary

This detached home located at 304 Winston Road, Oakville is currently for sale and has been available on SousaSells for 100 days. This property is listed at $4,298,000 with an estimated mortgage of $14,306* per month. It has 5 beds, 6 bathrooms, and is 3500-5000 square feet. 304 Winston Road, Oakville is in the West neighborhood.

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* Estimated mortgage assumes a 30% down payment, 4.00% interest rate, and 30-year amortization.
Is this a Good Home for Families?

Yes! Featuring 5 bedrooms and 6 bathrooms, this home offers ample space and comfort for growing families in West, Oakville.

Highly Recommended for Families
What We Love About This Home
  • •5 spacious bedroom layout offering versatile living space
  • •6 well-appointed bathrooms
  • •3500-5000 sqft of generous functional square footage
Standout Features & Layout
Who Should Buy This Home?

Growing families needing multi-bedroom flexibility and space in West, Oakville.

Target Buyer Match

Key Features

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

Additional Details

StatusPrice Change
AddedMay 21, 2026 (100 days ago)
UpdatedJun 18, 2026 (72 days ago)
Last Checked8 minutes ago
Transaction TypeFor Sale

Property Details

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

Parking & Garage

Parking Total8.0
Parking Space6
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

None listed

Frequently Asked Questions about 304 Winston Road, Oakville, ON

Q.What is the asking price for 304 Winston Road, Oakville, ON ?

The current listing price for 304 Winston Road, Oakville, ON in West, Oakville is $4,298,000.

Q.How many bedrooms and bathrooms does this property have?

This property features 5 bedrooms and 6 bathrooms across approximately 3500-5000 sqft.

Q.What property type and architectural style is 304 Winston Road, Oakville, ON ?

304 Winston Road, Oakville, ON is a Detached (2-Storey) featuring a Full, Finished basement.

Q.What key property features does 304 Winston Road, Oakville, ON offer?

Key property features include: School, Park, Lake/Pond.

Q.What interior features are included in this home?

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

Q.What security features are installed at 304 Winston Road, Oakville, ON ?

Security features include: Carbon Monoxide Detectors, Security System.

Q.Is parking available at this property?

Yes, this property offers parking space for 8.0 vehicles (Attached).

Q.What heating and cooling systems are installed?

Heating is provided via Gas and cooling via Central Air.

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Location

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304 Winston Road, Oakville, ON

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Neighborhood Safety Index

Neighborhood Safety & Crime Analytics

West Oak Trails, Oakville

SAFETY RATING9.4 / 10
Low Incident Area
Total Annual Incidents68 incidents / yr
Average Per Month5.7 incidents / mo
Population Benchmark32,000 residents
Personal Safety
Very Low

16 assaults (50.0/100k)

Property Security
Low

14 B&E (43.8/100k)

Auto Theft Risk
Moderate

22 thefts (68.8/100k)

1-Year Trend
â–Ľ 5.2%

Improving vs previous year

How Per-Capita Rate (Per 100,000 Residents) Is Calculated:

Formula: (Annual Occurrences / Population) Ă— 100,000. This standard policing calculation normalizes incident frequencies across different population sizes, allowing accurate safety comparisons between quiet residential pockets and dense urban centres.

Source: Halton Regional Police Service (HRPS) Open Data
Halton & GTHA Police Network

Disclaimer: Crime and safety analytics are compiled from official municipal and regional police open data records for general consumer informational and demographic research purposes only. Data is deemed reliable but is not guaranteed and does not constitute a legal representation or guarantee of future safety.

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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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Properties in this area are selling at a steady pace.

Market Trend
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Mortgage & Affordability Audit

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

Configure Loan Settings

Interest Rate4.00%
Down Payment$1,289,400 (30.0%)
* Minimum Canadian down payment required for this price is $859,600.
Amortization Period30 Years
Estimated Monthly Payment$14,306Based on a loan of $3,008,600 over 30 years.
Purchase Price$4,298,000
Loan Amount$3,008,600
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.

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West, Oakville Neighborhood Guide

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

Verified Local Data
City Population213,759
City Median Age41.5 Yrs
City Ownership82% Owners
Avg Area List Price$2,226,853

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%

Best Schools in West, Oakville

Elementary Schools

Brookdale
Public1195 Bridge Road, Oakville, Ontario, L6L 2C3
6.5
Patricia-Picknell
Public1257 Sedgewick Crescent, Oakville, Ontario, L6L 1X6
8.8
Pine Grove
Public529 Fourth Line, Oakville, Ontario, L6L 5A8
7.9
Gladys Speers
Public2150 Samway Road, Bronte, Oakville, Ontario, L6L 2P6
7.7
W H Morden
Public180 Morden Road, Oakville, Ontario, L6K 2S3
8.5

Secondary Schools

Thomas A Blakelock
Public1160 Rebecca Street, Oakville, Ontario, L6L 1Y9
8.1
St. Thomas Aquinas
Catholic124 Dorval Drive, Oakville, Ontario, L6K 2W1
8.2

West, Oakville Demographic Home information

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.

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