$2,549,000
FOR SALE

Detached 2-Storey

Bedrooms: 4Bathrooms: 5Lot: 57.48 x 137.22 ft
2025 Taxes: $10,858

2203 Winding Woods Dr
Oakville, ON L6H 5T9 | 1015 - RO River Oaks | Halton

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.
Extras
Auto Garage Door Remote, Central Vacuum
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Listed By RE/MAX ESCARPMENT REALTY INC.
Data Provided By Toronto Regional Real Estate Board
MLS® Listing Number W13064222
Last Updated Apr 30, 2026
Property Summary
Property Type Detached

More like this:
PIN 250640043
Legal Description PCL40-1, SEC 20M531; LT 40, Plan M531, Oakville
Possession Date Flexible
Taxes (2025) $10,858
Directions/Cross Streets River Oaks Blvd/Winding Woods
Neighbourhood 1015 - RO River Oaks
Area Halton
Price History

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Detailed Information
Fronting On East
Special Designations Unknown
Bedrooms 4
Bathrooms 5
Lot 57.48 x 137.22 ft
Exterior Brick
Air Conditioning Central Air
Family Room Y
Fireplace/Stove Y
Basement Finished
Garage Type Attached
Garage/Park Spaces Y
Parking Spaces 4
Heat Source Gas
Heat Type Forced Air
Sewers Sewer

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