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 Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
0-5
Total Approx Floor Area:
3500-5000
Lot Depth:
163'49.7 m
Lot Frontage:
77'23.5 m
Direction Faces:
South
Bedrooms:
4+1
Bathrooms:
6.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
4
Bedrooms Below Grade:
1
Kitchens Above Grade:
1
Rooms Above Grade:
12
Rooms Below Grade:
5
Heating type:
Forced Air
Heating Fuel:
Gas
Fireplaces:
2
Foundation:
Concrete
Roof:
Asphalt Shingle, Asphalt Rolled
Basement:
Full, Finished
Fireplace Features:
Family Room, Natural Gas
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
2.0
Parking Features:
Private Double
Parking Spaces:
6
Total Parking Spaces:
8.0
Family Room:
Yes
Possession Details:
90+ days
Lot Irregularities:
77.13 x 163.07 x 64.10 x13.92 x150.26 ft
Pool:
Salt, Inground
Link:
No
HST Applicable To Sale Price:
Included In
Assessment Year:
2025
Taxes:
$17,126.65 /
2025
Assessment:
$- /
2025
Halton
Oakville
1020 - WO West
School, Park, Lake/Pond
Generator - Full, Primary Bedroom - Main Floor, Air Exchanger, Central Vacuum, Auto Garage Door Remote, Water Heater Owned, Sump Pump, ERV/HRV, Bar Fridge
Hot Tub, Porch, Landscaped
Carbon Monoxide Detectors, Security System
Subzero fridge, Subzero freezer, Subzero wine fridge, Wolf induction cooktop, Wolf wall oven, Wolf microwave, Cove dishwasher, Asko Dishwasher, Miele washer, Miele Dryer, Samsung washer, Samsung gas dryer, Generator, Pool equipment, window coverings, ELFS, Garage remotes, Central vac accessories, Family room TV, Primary bedroom TV, Outdoor covered porch TV, Gym TV.
TV and wall mount in upstairs bedroom, 2 speakers and subwoofer in main floor family room.
None
Brick, Stone
Yes
Elevator, Open Floor Plan, Hallway Width 42 Inches or More
Data was last updated June 5, 2026 at 09:15 PM (UTC)
Area Statistics
Listings on market:
112
Avg list price:
$1,689,450
Min list price:
$950,000
Max list price:
$4,738,888
Avg days on market:
30
Min days on market:
0
Max days on market:
624
These statistics are generated based on the current listing's property type
and located in
1020 - WO West. Average values are
derived using median calculations. This data is not produced by
the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.