Welcome to 362 Winston Road, a sophisticated South Oakville residence situated on a coveted street surrounded by custom multimillion-dollar homes, and walking distance from Appleby College. This deceptively large, renovated bungalow features an amazing, multi-level rear addition that dramatically expands its square footage and provides distinct, functional living zones. The heart of the addition is a spacious ground-floor family room with a gas fireplace, large windows, and a direct walk-out to a private, west-facing backyard. Positioned on its own dedicated upper level, the expansive primary bedroom retreat serves as a private sanctuary complete with a sitting area, skylight, generous closet space, and a 5-piece ensuite. The original main level accommodates daily living with hardwood floors, solid wood California shutters, an updated skylit kitchen, a breakfast nook, a formal dining room, two additional bedrooms, and a 4-piece bathroom. The home's footprint extends into a fully finished lower level, significantly increasing functional space with a large recreation room, home office, gym, laundry area, full 3-piece bathroom, and extensive storage. With four full bathrooms distributed throughout, the layout effortlessly accommodates families and guests. Externally, the property features a rare, oversized attached four-car garage and mature landscaping. This property offers a rare blend of space, privacy, and location in one of South Oakville's premier enclaves.More details
Listed by Royal LePage Realty Plus Oakville, Brokerage
Welcome to The Arboretum, a gated condominium community located in the heart of Glen Abbey-one of Oakville's most established and desirable neighbourhoods. Known for its beautifully maintained grounds, mature trees, and welcoming atmosphere, this sought-after community offers the perfect balance of peaceful living and everyday convenience. Offering approximately 1,400 sq. ft., this bright and spacious corner suite features two bedrooms, two full bathrooms, and a thoughtfully designed layout that is both functional and inviting. Large windows flood the home with natural light, while the open-concept living and dining areas provide an ideal setting for both quiet relaxation and entertaining. The added convenience of in-suite laundry completes the main living space. The primary suite serves as a true retreat, featuring a generous bedroom, a walk-in closet, and a 5-piece ensuite with a double vanity, separate shower, and deep soaker tub. The second bedroom offers great versatility as a guest room or home office and sits just steps from the second full bathroom. In the recently updated kitchen, modern finishes combine with abundant cabinetry and counter space to create a room that is as stylish as it is practical. Just off the main living area, step onto your private balcony to enjoy serene, tree-lined views-the perfect backdrop for morning coffee or evening unwinding. Residents of The Arboretum enjoy access to top-tier amenities, including an indoor pool, hot tub, sauna, fully equipped fitness facility, tennis courts, guest suites, and a spacious party room for hosting gatherings. Ideally located minutes from Glen Abbey Golf Club, the scenic trails of Sixteen Mile Creek, local shops, top-rated schools, and major transit routes (QEW, Highway 407, and Oakville GO), this property blends lifestyle, location, and effortless luxury.More details
5 Elite Picks! Here Are 5 Reasons To Make This Home Your Own: 1. Stunning Updated Kitchen (Sept. '26) Featuring Dual-Tone Cabinetry, Quartz Countertops & Backsplash, Updated Stainless Steel Appliances & Bright Breakfast Area with Oversized Picture Window! 2. Generous Principal Rooms Including Lovely Formal Living Room, Separate Formal Dining Room & Spacious Family Room with Fireplace & Patio Door W/O to Deck & Backyard. 3. Contemporary Updated Staircase (Sept. '26) Leads to 2nd Level with 3 Bedrooms & 2 Updated Baths (Sept. '26), Including Spacious Primary Bedroom with Large W/I Closet & 4pc Ensuite. 4. Nearly 2,000 Sq.Ft. of Above-Ground Living Space Plus Over 1,000 Sq.Ft. in the Unspoiled Open Basement with Freshly Painted Floor (Sept. '26) - Bring Your Design & Finishing Ideas!! 5. Lovely Fully-Fenced Backyard Boasting Updated Deck (Sept. '26), Mature Trees & Beautiful Perennial Gardens! All This & More! Enclosed Porch Entry to Bright 2-Storey Foyer. Convenient Side Entrance & Modern 2pc Powder Room Complete the Main Level. Modern 3pc Main Bath with Glass Shower. Complete Home Reno in Sept. 2026 Includes Updated Hardwood Flooring Thru Main Level, Updated Kitchen Cabinets & Appliances, Bathroom Cabinets, Sinks, Faucets & LED Mirrors, Updated Outlets, Switches & Light Fixtures, Updated Wiring & Plumbing in Bsmt Laundry Area & More! Freshly Painted & Move-in Ready! New Heat Pump A/C & Furnace '23, New Garage Door Opener '18, Updated Windows & Doors Approx.'18. Fantastic Location on Quiet Crescent in Sought-After Glen Abbey Neighbourhood, Just Minutes to Parks & Trails, Golf Clubs, Top Schools, Hwy Access & Many More Amenities!More details
Beautifully Renovated 3+2 Bedroom Bungalow in Desirable South Oakville, Featuring an Oversized Detached Tandem Garage with an Impressive 1,084 Sq. Ft. Loft Above (Per MPAC)! Extensively renovated throughout, this home boasts a bright open-concept living and dining area, elegant hardwood flooring, and a stunning modern kitchen with a large quartz island, upgraded cabinetry, and stainless steel appliances. The main floor offers 3 bedrooms and a beautifully updated 4-piece bathroom, while the finished basement features a spacious recreation room, 2 additional bedrooms, and a 3-piece bathroom. An expansive deck seamlessly connects the main residence to the detached garage and spacious upper loft, offering exceptional versatility for a home office, studio, gym, or creative retreat. Professionally designed plans were previously approved in 2024 for a proposed two-bedroom accessory dwelling unit, offering exciting conversion potential. The deep tandem garage accommodates 2 vehicles, plus driveway parking for up to 5 more. Ideally located near parks, schools, Appleby College, and the lakefront. A truly unique property combining modern comfort, exceptional space, and remarkable potential! Additional updates include roof, furnace and central A/C (2019), in-ground sprinkler system (2019), and washer & dryer (2025). Hot water tank is owned.More details
TOP-FLOOR LIVING IN SOUGHT-AFTER GLEN ABBEY! Exceptional value in this rarely offered spacious 2-bedrooms, 1-bathroom condo, one of the largest units in this desirable complex, ideally located in Oakville's family-friendly Glen Abbey community within a highly regarded school catchment. Enjoy the benefits of top-floor living with no neighbours above, added privacy, reduced overhead noise and beautiful views of mature trees. Hardwood flooring throughout adds warmth and elegance complementing the spacious layout and abundant natural light. The generous kitchen features stainless steel appliances and ample prep space, while the separate dining area is ideal for entertaining. Relax by the cozy living room fireplace or step onto the large balcony to enjoy your morning coffee, fresh air and peaceful treed views. A massive pantry offers exceptional storage rarely found in condo living. The spacious primary bedroom features two large windows and a generous walk-in closet with access to the bathroom. Additional highlights include in-suite laundry, underground parking and a large in-suite locker. Enjoy fantastic building amenities, including a gym, sauna and games room with pool table. Perfect for first-time buyers, downsizers or investors seeking space, convenience and value. Located in desirable Glen Abbey, known for its mature tree-lined streets, parks, walking trails, excellent schools and recreational facilities. Groceries, shopping, restaurants and public transit are less than a minute away, making everyday errands and commuting effortless. Space, sunlight, privacy and convenience - this exceptional top-floor condo checks all the boxes! Don't miss this opportunity to enjoy convenient, low maintenance living in one of Oakville's most sought-after communities.More details
Popular Mattamy 'Chamberlain' model offers 3136 SF with hardwood on both levels. 4 bedrooms, 2.5 baths with main floor office/den. All bathrooms beautifully renovated in 2020; Windows 2016; Roof tiles 2015; Kitchen 2015. Move-in ready with an unspoiled basement ready for your creative finishes. Main floor family room with wood burning fireplace, wainscotting & crown moulding. Eat-in breakfast area with walkout to large deck, pool sized yard with stone surround that nicely frames the yard, perfect for all your gardening needs. Ideal Glen Abbey location on quiet street with easy access to top rated schools, recreation centre, parks, trails and shopping.More details
Listed by RE/MAX Aboutowne Realty Corp., Brokerage
An exceptional opportunity in one of Oakville's most sought-after neighborhoods, south of Rebecca Street in Southwest Oakville. Situated on a premium 75' x 150' lot, this well-maintained home and property offers endless possibilities even for builders, investors, renovators. The existing bungalow features a single-car garage, 2 kitchens, 3 bedrooms, 2 bathrooms, and a spacious lower-level recreation room with fireplace. While the home offers potential, the true value lies in the outstanding lot and its prime location just south of Rebecca, a short 2-3-minute drive to the lake, Coronation Park, 5 minutes to Downtown Oakville and Bronte Marina and Bronte Village. Rarely do properties of this size and location calibre become available in such a prestigious setting. Bring your vision and explore the possibilities. Thank you for showing.More details
Welcome to this spacious 4+1-bedroom, 4-bathroom detached family home, ideally situated in sought-after Glen Abbey and backing onto peaceful green space.A double-door entrance opens to an impressive foyer with a grand staircase and leads into featuring hardwood flooringoffers plenty of cabinetry, generous prep space and a spacious eat-in area, with direct access to a beautiful multi-tiered deck overlooking the private backyard oasis.The inviting family room is centred around a gas fireplace with a classic brick surround, creating a warm and comfortable space for everyday living. A convenient mudroom provides additional storage, a double-door closet and a separate side entrance.Upstairs, you'll find four generously sized bedrooms, including a spacious primary retreat complete with a walk-in closet and grand four-piece ensuite. Three additional well-proportioned bedrooms and a full main bathroom provide plenty of room for the entire family.The finished lower level adds even more versatile living space with a large recreation area, three-piece bathroom and an additional room perfect for a fifth bedroom, home office, gym or guest space.Outside, the multi-tiered deck and private backyard create a true retreat, made even more special by the tranquil green space beyond. Offering generous living space inside and out, this is a wonderful opportunity to enjoy a well-appointed family home in one of Oakville's most established and desirable communities.More details
Listed by RE/MAX Escarpment Realty Inc., Brokerage and RE/MAX ESCARPMENT REALTY INC.
A bold statement in luxury living. Set on an impressive 75 x 150 ft. lot in prestigious SouthOakville, this newly built custom residence offers approximately 6,200 sq. ft. of meticulouslydesigned living space, where striking architecture meets exceptional craftsmanship.Soaring 11-foot ceilings lead to a breathtaking double-height great room with expansive windowsoverlooking a pool-sized backyard. The showstopping chef's kitchen features premium Wolf andThermador appliances, exquisite countertops, custom cabinetry, and a walk-in pantry.A sophisticated main-floor office with arched glass doors, two closets, and a privatethree-piece bathroom offers exceptional versatility. Upstairs, four spacious bedrooms provideluxurious private retreats, while the fully finished lower level is designed for entertainingwith a home theatre, wet bar, and generous recreation spaces.Just minutes from Downtown Oakville, the lake, parks, and amenities, 1415 Rebecca Street is arare offering of scale, sophistication, and timeless design in one of Oakville's most covetedneighbourhoods.More details
Data was last updated October 27, 2026 at 02:15 AM (UTC)
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