304 Winston Road

FOR SALE
$4,298,000
304 Winston Road, Oakville
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
304 Winston Road
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4 + 1
BEDROOMS
6
BATHROOMS
1
KITCHENS
12 + 5
ROOMS
W13159190
MLSID
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Property 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.
Sold History
List Date Sold Date Days Listed List Price Sold Price
2019-07-15 2019-08-09 25 $1,199,900 $1,160,000
Nearby Intersections
Property Features
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, Private Double, Carbon Monoxide Detectors, Security System, Family Room, Natural Gas, Elevator, Open Floor Plan, Hallway Width 42 Inches or More
Property Details
Address
304 Winston Road
Postal Code
L6L 4W5
Property Type
Detached, Detached
Lot Size
77' x 163'
Taxes
$17,127 (2025
Basement
Full, Finished
Exterior
Hot Tub, Porch, Landscaped
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Pool
Salt, Inground
Parking Spaces
6
Garage Type
Attached
Listing contracted with Re/Max Aboutowne Realty Corp.
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BEDS
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BATHS
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BEDS
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4+1
BEDS
5
BATHS
$3,898,000
FOR SALE
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$3,895,000
FOR SALE
A home that effortlessly commands attention, defined by bold contemporary architecture and refined curb appeal. Set within South-East Oakville's Morrison neighbourhood, the striking exterior blends natural cedar and stone-creating a sophisticated façade that feels both modern and timeless, offering over 5,700 sqft of total living space. The dramatic 21ft foyer with floating glass staircase sets the tone, leading into an open-concept main level with 10-foot ceilings. With its prized southern exposure, the main living spaces are framed by a wall of floor-to-ceiling glass sliding doors with phantom screens-introducing remarkable scale while seamlessly inviting the outdoors in. The chef's kitchen is anchored by a 12ft island and features premium Wolf and SubZero appliances, along with a walk-through servery complete with wine fridge and access to the dining room. The great room impresses with custom built-ins, a gas fireplace, and a statement walnut feature wall. Also on the main level, a quiet office, powder room, convenient laundry room and mudroom entry from the double car garage. Upstairs, four spacious bedrooms offer ensuite access, including a luxurious principal retreat with double walk-in closets and a spa-like ensuite. The fully finished lower level with 9ft ceilings, adds exceptional versatility with a large recreation space, built-ins, electric fireplace, fifth bedroom or gym, and a 3-piece bathroom with a steam shower. The backyard, enveloped by a lush canopy of trees, where the gentle sights and sounds of the nearby creek create a serene retreat immersed in nature. Privacy, serenity and beautifully landscaped, the deck and stone patio are perfectly designed for entertaining. Additional highlights include an 8-vehicle driveway, irrigation system, and a fully integrated smart home with built-in speakers, Lutron lighting, and motorized blinds throughout. Positioned just moments to top-rated schools, parks, and downtown.
411 Wedgewood Drive, Oakville
4+1
BEDS
5
BATHS
$3,788,000
FOR SALE
Situated in highly coveted South East Oakville, this custom-built 4,200 square foot masterpiece offers luxury living in an elite location close to the very best public and private schools Halton has to offer. Designed for grand entertaining and effortless family life, the home opens with a soaring great room featuring dramatic high ceilings and abundant natural light. The main floor centers around a chef-inspired open-concept kitchen and breakfast area that seamlessly connects to a functional butler's pantry for easy hosting. A massive combined living and dining room space sets the stage for formal gatherings, while a private main-floor office provides a quiet retreat for remote work. The upper level delivers spacious accommodations tailored for comfort. The massive primary suite acts as a private sanctuary, featuring a sprawling walk-in closet and a spa-like 5-piece ensuite bath. The second bedroom offers its own double closet and a private 3-piece ensuite. Completing the upper floor, two additional oversized bedrooms share a beautifully finished 5-piece dual-vanity ensuite. Step outside into an exceptional backyard oasis framed by mature trees for complete privacy. The expansive grounds feature a spacious back deck for outdoor dining and an award-winning saltwater pool complete with two cascading rock waterfalls. Downstairs, the large and bright finished basement provides a fantastic secondary living zone. Centered around a cozy fireplace, this flexible area is ideal for recreation, complimented by a private 5th bedroom perfect for guests, teens, or an in-law suite. Combining custom architecture, resort-style amenities, and an unbeatable location in one of Oakville's premier school districts, this home represents a truly extraordinary opportunity! Luxury Certified.
1179 Carey Road, Oakville
4+1
BEDS
5
BATHS
$3,450,000
FOR SALE
Exceptional contemporary family home on a premium 87x 179 southwest lot on one of Southeast Oakville's most sought-after streets, just steps to top-ranked public schools and prestigious private schools including Linbrook School & St. Mildred's-Lightbourn School. Offering over 5,000 sq. ft. of beautifully finished living space, this impressive residence offers modern design and exceptional family functionality. A generous foyer creates a stunning first impression, with sightlines extending through the home to the beautifully landscaped rear gardens. Professionally designed outdoor living features extensive hardscaping, an inground pool, hot tub, covered gazebo, fire pit zone, and landscape lighting, creating a private resort-like setting for entertaining and family enjoyment. The thoughtfully designed layout offers 4+2 bedrooms and 3+2 bathrooms. All bedrooms feature built-in closets, while the luxurious primary suite boasts dual walk-in closets and a spa-inspired ensuite with double vanity, soaker tub, and separate shower. The heart of the home is a stunning contemporary kitchen overlooking the spacious family room with a gas fireplace and wall of sliding glass doors opening to the private backyard oasis. Elegant principal rooms include a formal living room with fireplace and oversized windows, a separate dining room, a dedicated main floor office, and a well-appointed mudroom with inside access to the attached two-car garage.The fully finished lower level includes a spacious rec room with gas fireplace, adjoining billiards area, two additional bedrooms, a sauna, laundry room with second refrigerator, direct access to the side yard-ideal for guests, extended family, or recreation. Nestled on one of Southeast Oakville's most desirable streets, this exceptional property offers the charm and tranquility of an established neighbourhood with mature trees, beautiful parks, and convenient access to lakeside parks and Downtown Oakville.
442 Sherin Drive, Oakville
4+2
BEDS
5
BATHS
$3,300,000
FOR SALE
Welcome to this exceptional custom-built home in the heart of South Oakville, where timeless design meets modern luxury. Offering 3,387 sq. ft. above grade (MPAC) and approximately 5,400 sq. ft. of beautifully finished living space, this residence was thoughtfully designed for comfortable family living and elegant entertaining.The sun-filled open-concept layout features dramatic floor-to-ceiling windows, 10-foot ceilings on the main floor, and premium finishes throughout. The gourmet kitchen is the centerpiece of the home, complete with custom white cabinetry, quartz countertops, high-end appliances, and a large centre island overlooking the spacious family and dining areas.This home offers 4+2 generously sized bedrooms, a private main-floor office, and 5 beautifully finished bathrooms, providing plenty of space for growing families. The professionally finished walk-up basement with 9-foot ceilings includes an oversized recreation room, wet bar, exercise area, and two additional bedrooms, making it ideal for entertaining or extended family living.Step outside to a professionally landscaped backyard featuring a covered cedar-ceiling patio, creating the perfect setting for relaxing or hosting family and friends.Situated in one of South Oakville's most desirable neighbourhoods, this home is within walking distance to parks, shopping, Appleby College, Queen Elizabeth Park Community and Cultural Centre, and is just minutes from the lake. It is also surrounded by some of the area's top-rated public, Catholic, and private schools.Proudly built by the owner for personal use-not as a speculative build-this home reflects exceptional craftsmanship, quality materials, and meticulous attention to detail throughout. This is a rare opportunity to own a truly remarkable custom home in one of Oakville's most sought-after communities.
431 Seaton Drive, Oakville
4+2
BEDS
5
BATHS
$3,299,000
FOR SALE
Beautifully custom-built home showcasing luxury finishes throughout in one of the area's most prestigious and highly sought-after neighbourhoods. Boasting stunning curb appeal with a timeless stone exterior and an oversized driveway accommodating up to 6 vehicles, this exceptional residence blends elegance, comfort, and functionality. Designed with impeccable attention to detail, the home features elegant herringbone white oak flooring, soaring floor-to-ceiling windows in the family room, and a skylight that fills the main floor with an abundance of natural light. The chef-inspired kitchen offers quartz countertops, premium finishes, and ample space for both entertaining and everyday living. Beautiful custom drapery throughout the home adds warmth and sophistication to every space. The fully finished entertainer's basement is a true showstopper featuring a massive custom bar, rough-in completed for heated flooring, and a convenient separate entrance from the backyard offering endless possibilities for hosting, extended family, or future potential. The garage is thoughtfully designed with an additional rear garage door providing easy backyard access, perfect for storage, lawn equipment, and added convenience. Located in a prestigious and highly desirable neighbourhood close to top-rated schools, parks, shopping, and major amenities. Too many upgrades and features to mention - this is a must-see home that truly stands apart. Book your private viewing today!
287 Macdonald Road, Oakville
4
BEDS
5
BATHS
$3,949,000
FOR SALE
This completely renovated contemporary residence represents the pinnacle of modern design and sophisticated living in one of Oakville's most desirable locations of Old Oakville.Every detail of this 4 Bedroom | 4+1 Bathrooms | 4,819 Sq Ft Finished Living Space has been meticulously reimagined to deliver an unparalleled standard of quality and craftsmanship.The highly functional main floor plan centers around an exceptionally sleek kitchen open to the Great Room with gas fireplace and walk out to the resort style backyard and pool.The kitchen is outfitted with luxury high-end appliances, an oversized island seating eight, and an additional peninsula for casual entertaining in the bar area.Adjacent to the kitchen, is a walk in pantry with an additional dishwasher and fridge. Not to be missed is the impressive temperature-controlled wine room accommodates approx 1,000 bottles-a striking feature for the discerning entertainer.A versatile family room/main floor bedroom with ensuite which can be used as a principal bedroom or guest suite, laundry room, walk-in main closet for storage and access to oversized double car garage.The 2nd level principal suite is a private sanctuary featuring juliette balcony, gas fireplace, two walk-in closets and a spa-inspired ensuite with heated floors, walk-in shower, and a standalone soaking tub.Two additional spacious bedrooms each with their own ensuites complete the level. Not to be missed is the finished lower level room with added storage in the pantry and crawl space area. The backyard is an entertainer's paradise, showcasing a saltwater pool, two expansive patio areas, two gazebos with a gas fire table, and premium Dutch-imported artificial turf that remains lush year-round with zero maintenance.Ideally situated steps from Whole Foods Market, Oakville GO Train, for seamless transit connectivity,and the Oakville Trafalgar Community Centre this extraordinary property offers both refined luxury and everyday convenience.LUXURY CERTIFIED
153 Cairncroft Road, Oakville
4
BEDS
5
BATHS
$3,890,000
FOR SALE
Nestled on an exceptional 15,511sqft mature lot in prestigious Southeast Oakville, this beautifully renovated executive residence offers timeless elegance, luxurious finishes, and an unbeatable location within walking distance to top-ranked schools, including OTHS, EJ PS etc. Offering approximately 3487 sqft. above grade plus a finished lower level, this exceptional home features 4 bedrooms, 5 bathrooms, and thoughtfully designed living spaces perfect for both family living and entertaining.Rich wide-plank hardwood floors, crown mouldings, custom millwork, wainscoting, built-ins, pot lights, stone flooring, an impressive oak staircase with iron pickets, and four gas fireplaces showcase the home's exceptional craftsmanship. The stunning renovated chef's kitchen is appointed with premium Miele appliances, custom cabinetry, and overlooks the inviting sunken family room, creating the perfect gathering space. Elegant formal living and dining rooms provide refined spaces for entertaining, with the living room easily accommodating a baby grand piano.The luxurious primary retreat features its own gas fireplace, an expansive dressing room, and a spa-inspired 4-piece ensuite with a glass shower. The finished lower level offers a spacious recreation room, exercise room, 2-piece bath, and abundant storage.Extensive updates include a complete kitchen renovation, premium Miele appliances, exterior LED lighting, renovated garage, repaved driveway, new eavestroughs, freshly painted exterior façade, new pool liner and heater, and numerous quality improvements throughout.The spectacular backyard is a private oasis featuring a sprawling stone patio, covered terrace, and sparkling in-ground pool surrounded by mature landscaping-perfect for summer entertaining. Ideally located just steps to Lake Ontario, Gairloch Gardens, parks, trails, and only a 3-minute drive to downtown Oakville's boutique shops, fine dining, and waterfront.
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