304 Winston Road

304 Winston Road
304 Winston Road
304 Winston Road
+42
4+1
 bed
6
 bath
8
 parking
3500 - 5000
 sqft
Detached
$4,480,000
For Sale
6 days
 on site
$4,480,000
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Size
-
Lot size
12551 sqft
Street frontage
-
Possession
90+ days
Price per sqft
$896 - $1,280
Taxes
$17,126.65 (2025)
Parking Type
-
Style
2-Storey
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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.
Broker: RE/MAX ABOUTOWNE REALTY CORP.
MLS®#: W13159190
Property details
Parking:
8
Parking type:
-
Property type:
Detached
Heating type:
Forced Air
Style:
2-Storey
MLS Size:
3500-5000 sqft
Lot front:
77 Ft
Lot depth:
163 Ft
Listed on:
May 22, 2026
Show all details
Rooms
LevelNameSizeFeatures
Second
Bedroom 4
14.3 x 11.6 ft
Basement
Exercise Room
14.0 x 16.4 ft
Main
Mud Room
13.0 x 7.5 ft
Show all
Instant estimate:
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$93,536
lower than listed price
i
High
$4,600,636
Mid
$4,386,464
Low
$4,193,194
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About 304 Winston Road

304 Winston Road is an Oakville detached house for sale. It was listed at $4480000 in May 2026 and has 4+1 beds and 6 bathrooms. 304 Winston Road, Oakville is situated in Bronte East, with nearby neighbourhoods in Old Oakville, Glen Abbey, Bronte West and College Park.

Nearby grocery options: M&M Food Market is a 12-minute walk.

If you are reliant on transit, don't fear, 304 Winston Rd, Oakville has a public transit Bus Stop (Rebecca St / Maplehurst Ave) only steps away. It also has route Lakeshore West, and route Lakeshore West close by.