2203 Winding Woods Drive

FOR SALE
$2,549,000
2203 Winding Woods Drive, Oakville
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
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4
BEDROOMS
5
BATHROOMS
1
KITCHENS
9 + 2
ROOMS
W13064222
MLSID
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Property Description
Set on one of River Oaks' most coveted streets, known for its estate-sized lots and executive homes, this is a rare opportunity to own a residence that feels completely immersed in nature. With forest and walking paths wrapping the rear and south side, and a ravine beyond, the setting is incredibly private-something almost unheard of in Oakville. Offering over 4,200 sq. ft. above grade and 6,000 sq. ft. of finished living space, the home has been impeccably maintained and thoughtfully upgraded, blending scale, warmth, and timeless character. At its heart is a truly exceptional custom kitchen by BINNS Kitchens of Toronto, a $285K investment designed for those who love to cook and entertain. Anchored by a dramatic 15 ft island and equipped with Sub-Zero and Wolf appliances, the space is as functional as it is striking. It flows effortlessly into a sun-filled solarium with four skylights and garden doors on both sides, opening to two private decks and creating a seamless indoor-outdoor experience. The main floor offers beautifully proportioned principal rooms, a welcoming family room with wood-burning fireplace, a refined dining space with architectural openings that allow light to move through the home, and a versatile front den perfect as a library or office. Upstairs, four generous bedrooms and three full baths provide comfort for family and guests, along with a separate study tucked behind French doors. The lower level is designed for unforgettable evenings, featuring a classic wood bar with brass rail, a full-size snooker table, gas fireplace, and abundant space to relax, entertain, or unwind-complete with a steam shower bathroom. Surrounded by mature landscaping, enhanced with stonework, lighting, irrigation, and modern conveniences including a Tesla charger, this is a home that offers not just space, but a lifestyle-private, inviting, and truly rare.
Property Features
Electric Car Charger, Hospital, Park, Golf, Rec./Commun.Centre, Wooded/Treed, Auto Garage Door Remote, Central Vacuum
Property Details
Address
2203 Winding Woods Drive
Postal Code
L6H 5T9
Property Type
Detached, Detached
Zoning
RL5
Lot Size
58' x 137'
Taxes
$10,858 (2025
Basement
Finished
Exterior
Lawn Sprinkler System, Landscape Lighting
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
4
Garage Type
Attached
Listing contracted with Re/Max Escarpment Realty Inc.
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5
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5
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$2,490,000
FOR SALE
High-quality European-style modern custom home ,Truly Luxury design with precise ceiling height control, European-style interiors, and elegant decorative molding with double garage in West River. Well-designed, efficient layout with open-concept plan, large central island with Italian cabinetry, 9' coffered ceilings, wide corridors, gourmet kitchen, and family room with gas fireplace. Second-floor primary retreat with walk-in closet & 5-pc ensuite. 2026 new deck with water protection. Three additional bedrooms with ensuite access. Finished basement with rec room, guest bedroom, 3-pc bath, and walk-up entrance. Walk to Kerr Village, GO, schools, parks, harbour & lakefront.
2238 Lyndhurst Drive, Oakville
4
BEDS
4
BATHS
$2,449,000
FOR SALE
MOVE BEYOND THE STANDARD in Oakville's prestigious Joshua Creek. This refined 4,200+ SF residential asset is a masterclass in architectural volume and intentional flow. Engineered for grand-scale entertaining, the residence opens to a soaring double-height foyer and a curved staircase, leading into a light-filled living space anchored by a sophisticated two-sided gas fireplace. The formal dining room features custom coffered ceilings, while the chef-inspired kitchen and breakfast room offer a seamless transition to the private porch and rear grounds. STRATEGIC LAYOUT & DESIGN - A secondary staircase provides direct lower-level access, complemented by a dedicated mudroom/laundry and abundant storage solutions. The upper gallery leads to a primary suite designed as a private sanctuary, featuring a spa-caliber ensuite and dual walk-in closets. Three additional oversized bedrooms offer unparalleled versatility, including a semi-ensuite and a private ensuite with a custom window bench. PREMIER LOCATION & ACCESS - Positioned within the catchment of Ontario's top-tier institutions-Joshua Creek Elementary and Iroquois Ridge SS-this property offers proximity to elite golf clubs, tranquil trail systems, and rapid transit/highway corridors (403/QEW/407). Experience the intersection of luxury and logic. Move Beyond the Search.
259 Polly Drive, Oakville
5
BEDS
5
BATHS
$2,399,900
FOR SALE
Discover this spectacular Remington-built residence featuring a striking stone and stucco exterior, ideally situated on a premium ravine lot in the prestigious Preserve community. Offering approximately 4,471 sq. ft. of elegant living space, this home includes a fully finished loft, 10-ft ceilings on the main floor, and 9-ft ceilings on the second floor with a basement separate entrance, all nestled on a quiet, family-friendly street.Thoughtfully enhanced with recently upgraded flooring and modern fixtures throughout, the home showcases exceptional craftsmanship and attention to detail. Highlights include coffered ceilings, hardwood flooring on the main level, and a grand oak staircase with iron pickets.The gourmet kitchen is designed to impress, featuring granite countertops, high-end appliances, a centre island, and valance lighting-perfect for both everyday living and entertaining. The spacious family and living rooms are each anchored by their own fireplace, adding warmth and sophistication.All five generously sized bedrooms offer private ensuite bathrooms with quartz vanities, ensuring comfort and privacy for the entire family. A bright second-floor study with a large window can easily be converted into an additional bedroom.Beautifully interlocked and professionally landscaped, this exceptional property is truly move-in ready.Includes: Stainless steel fridge, gas stove, dishwasher, washer & dryer, all window coverings, all electrical light fixtures, garage door openers with remotes. Buyer to assume hot water tank rental.
1409 Tansley Drive, Oakville
4
BEDS
4
BATHS
$2,399,900
FOR SALE
*Power of Sale*Stunning, Custom-Built 4 Bedroom, 4 Bathroom Home Featuring Approximately 3,000 Sq. Ft. Of Finished Living Space In The Heart Of West Oakville. With Custom Features From Top To Bottom, This Home Offers An Abundance Of Natural Light And Features An Open Concept Main Floor w/Full Sized Kitchen And Dining Area, Walk-Out To Backyard, Open To Family Room And Formal Living/Dining Room. Second Floor Includes Four Generous-Sized Bedrooms, Primary Bedroom Includes Walk-In Closet W/Ensuite, Separate Laundry Closet. Unfinished Basement Includes Approximately 1,600 Sq. Ft. And Offers The Opportunity To Create More Living Space. Within Close Proximity To All Oakville Has To Offer, Including Bronte GO Station, Restaurants, Shopping, Golf Courses and Trails. Easy Access To QEW HWY.
2313 Coronation Drive, Oakville
4+1
BEDS
5
BATHS
$2,399,000
FOR SALE
Exceptional 4+1-bedroom, 4.5-bathroom executive home in prestigious Joshua Creek, offering approx. 3,460 sq ft above grade plus a professionally finished basement with separate staircase-ideal for in-law or multi-generational living. Located in the highly ranked Iroquois Ridge High School catchment (9.2/10 - Fraser Institute 2023/24), and steps to Iroquois Ridge Community Centre and Glenashton Park, this home blends top-tier schools, recreation, and convenience, with nearby shopping and restaurants at the Uptown Core, and close to major highways. Impressive curb appeal featuring a large shade tree, a flagstone porch, and a flagstone-trimmed driveway. The private, pool-sized backyard with cedar fencing, a 20' x 15' deck, a gazebo, an 8-person hot tub, a shed, and a natural gas BBQ, is perfect for entertaining. This sought-after Fernbrook "Melbourne" model showcases 9' ceilings, a dramatic 18' family room ceiling, maple hardwood flooring, an oak staircase with iron pickets, a second oak staircase from the main floor to the basement, 2 fireplaces, dual home theatre systems, 200-amp service, EV charger, and backup generator. The custom cherrywood kitchen by Paris Kitchens offers under- and over-cabinet lighting, granite counters, stainless steel appliances, and a walkout to the deck and yard, while the formal living/dining and a private office add versatility. Upstairs features 4 spacious bedrooms, a loft, and 3 full baths, including a luxurious primary suite with a spa-like ensuite. The finished basement includes a hidden theatre with a 12-foot screen and 4K projector, a kitchenette/wet bar, a 5th bedroom, and a 3-piece bath. Major updates include roof, A/C, on-demand hot water (2018), driveway resealed (2025), upgraded attic insulation and ventilation. Fabulous home!
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