2203 Winding Woods Drive, photo 1

For sale River Oaks, Oakville, ON

2203 Winding Woods Drive

List price
$2,199,000
Sq ft
3500-5000
Bedrooms
4
Bathrooms
5

About this home

Luxury Living set on one of River Oaks' most coveted streets! This residence is completely immersed in nature, with forest and walking paths wrapping the rear and south side, and a ravine beyond, the setting is incredibly private. Offering over 4,200 sq. ft. above grade and 6,000 sq. ft. of total 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 private lifestyle, inviting, and truly a rare opportunity.

Photos of 2203 Winding Woods Drive

Facts and features of 2203 Winding Woods Drive

Key facts
TypeDetached
Style2-Storey
Bedrooms4
Bathrooms5
Size3500-5000 sq ft
Lot57.55 x 137.43 Feet
Parking6
GarageAttached
HeatingForced Air
CoolingCentral Air
BasementFinished
ExteriorBrick
Taxes$11,070 (2026)
Days on market44
Listing brokerageRE/MAX ESCARPMENT REALTY INC.

Rooms

13 rooms, with sizes

RoomLevelSizeFeatures
Utility Room Basement 24′ 6″ × 12′ 11″
Office Basement 21′ 5″ × 10′ 5″
Recreation Basement 45′ 3″ × 22′ 8″
Primary Bedroom Second 29′ 4″ × 19′ 11″
Family Room Main 19′ 11″ × 13′ 6″
Den Second 18′ 1″ × 12′ 0″
Breakfast Main 21′ 11″ × 9′ 11″
Bedroom 4 Second 15′ 11″ × 12′ 11″
Dining Room Main 12′ 0″ × 19′ 4″
Living Room Main 17′ 11″ × 12′ 9″
Bedroom 2 Second 13′ 0″ × 12′ 0″
Kitchen Main 12′ 9″ × 25′ 11″
Bedroom 3 Second 16′ 7″ × 13′ 1″

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MLS® W13797086 Data source: PropTx Listed September 17, 2026