




$2,399,000
2203 Winding Woods Drive, Oakville, ON L6H 5T9
Oakville
- Bedrooms
- 4
- Bathrooms
- 5
- Parking
- 6
- Type
- Detached
About this listing
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' 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.
View Walk Score, Transit Score & Bike Score
Walkability, transit, and bike-friendliness for 2203 Winding Woods Drive, Oakville, ON L6H 5T9
Provided by Walk Score®. Walk Score, Transit Score, and Bike Score are trademarks of Walk Score.
MLS# W13227366
Listed by RE/MAX ESCARPMENT REALTY INC.
On market since Jun 2, 2026
About 2203 Winding Woods Drive, Oakville, ON L6H 5T9
How much is 2203 Winding Woods Drive, Oakville, ON L6H 5T9?
2203 Winding Woods Drive, Oakville, ON L6H 5T9 is listed for $2,399,000 CAD.
How many bedrooms and bathrooms does 2203 Winding Woods Drive, Oakville, ON L6H 5T9 have?
2203 Winding Woods Drive, Oakville, ON L6H 5T9 has 4 bedrooms and 5 bathrooms.
What type of property is 2203 Winding Woods Drive, Oakville, ON L6H 5T9?
2203 Winding Woods Drive, Oakville, ON L6H 5T9 is a Detached.
What neighbourhood is 2203 Winding Woods Drive, Oakville, ON L6H 5T9 in?
2203 Winding Woods Drive, Oakville, ON L6H 5T9 is in Oakville, Ontario.
Is 2203 Winding Woods Drive, Oakville, ON L6H 5T9 for sale or for rent?
2203 Winding Woods Drive, Oakville, ON L6H 5T9 is currently for sale.
How do I book a showing for 2203 Winding Woods Drive, Oakville, ON L6H 5T9?
Contact Michael Mezheritsky to arrange a private showing of 2203 Winding Woods Drive, Oakville, ON L6H 5T9 (MLS# W13227366). You can also send a message through the contact form on this site.