304 Winston Road, Oakville, ON L6L 4W5, Oakville, ON
Bed 5
Bath 6
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.
Property Highlights
For Sale
MLS NO.
W13159190
Type
Residential Freehold
Sub Type
Detached
Bedrooms
5
Bathrooms
6
Parking
8.0
Garage
Yes
Complete Property Details
Property Type
Residential Freehold
Sub Type
Detached
Transaction Type
For Sale
Status
Active
Contract Status
Available
MLS® Number
W13159190
Living Area Range
3500-5000
Total Bedrooms
5
Bedrooms Above Grade
4
Bedrooms Below Grade
1
Total Bathrooms
6
Total Kitchens
1
Kitchens Above Grade
1
Rooms Above Grade
12
Rooms Below Grade
5
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
Fireplace
Yes
Fireplace Features
Family Room, Natural Gas
Central Vacuum Yn
Yes
Security Features
Carbon Monoxide Detectors, Security System
Construction
Brick, Stone
Roof
Asphalt Shingle, Asphalt Rolled
Lot Width
77.0
Lot Size Units
Acres
Parking Features
Private Double
Parking Total
8.0
Covered Spaces
2.0
Garage Type
Attached
Garage
Yes
Pool
Salt, Inground
Direction Facing
South
Cooling
Central Air
Heat Source
Gas
Heat Type
Forced Air
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
304 Winston Road, Oakville, ON L6L 4W5
City
Oakville
Neighbourhood
1020 - WO West
County / Region
Halton
Province / State
ON
Postal Code
L6L 4W5
Cross Street
Maplehurst/Rebecca
Directions
Winston/Maplehurst
Country
CA
List Price
$4,298,000
Annual Taxes
$17,127
Tax Year
2025
Legal Description
LT 12, PL 579 ; S/T TW31604 OAKVILLE
Possession Type
90+ days
Possession Details
90+ days
Listing Office
RE/MAX ABOUTOWNE REALTY CORP.
Board
Toronto Regional Real Estate Board
Original Entry
2026-05-22T00:12:55Z
Media Updated
2026-06-30T16:37:26Z
Photos Updated
2026-06-30T16:37:26Z
Last Modified
2026-06-18T14:22:48Z
System Modified
2026-07-06T21:36:28.652882Z
MLS Status
Price Change
Architectural Style
2-Storey
Basement
Full, Finished
Ddfyn
No
Expiration Date
2026-10-31
Foundation Details
Concrete
Heat Source Multi
Gas, Other
Heat Type Multi
Forced Air
Hstapplication
Included In
Link Yn
No
Occupant Type
Owner
Originating System Id
A00001796
Parcel Number
248380049
Parking Spaces
6
Property Features
School, Park, Lake/Pond
Public Remarks
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.
