2203 Winding Woods Drive, Oakville

2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
+47
4
 bed
5
 bath
6
 parking
3500 - 5000
 sqft
Detached
$2,199,000
For Sale
42 days
 on site
$2,199,000
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Size
-
Lot size
7909 sqft
Street frontage
-
Possession
Flexible
Price per sqft
$440 - $628
Taxes
$11,070 (2026)
Parking Type
-
Style
2-Storey
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Description
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.
Broker: RE/MAX ESCARPMENT REALTY INC.
MLS®#: W13797086
Property details
Parking:
6
Parking type:
-
Property type:
Detached
Heating type:
Forced Air
Style:
2-Storey
MLS Size:
3500-5000 sqft
Lot front:
57 Ft
Lot depth:
137 Ft
Listed on:
Sep 17, 2026
Show all details
Rooms
LevelNameSizeFeatures
Basement
Utility Room
24.5 x 12.9 ft
Basement
Office
21.4 x 10.4 ft
Basement
Recreation
45.2 x 22.6 ft
Show all
Instant estimate:
orto view instant estimate
$191,662
lower than listed price
i
High
$2,105,348
Mid
$2,007,338
Low
$1,918,894
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About 2203 Winding Woods Drive

2203 Winding Woods Drive is an Oakville detached house for sale. 2203 Winding Woods Drive has an asking price of $2199000, and has been on the market since September 2026. This 3500-5000 sqft detached house has 4 beds and 5 bathrooms. 2203 Winding Woods Drive resides in the Oakville River Oaks neighbourhood, and nearby areas include College Park, Uptown Centre, Rural Oakville and West Oak Trails.

For those that love cooking, M&M Food Market is a 9-minute walk.

For those residents of 2203 Winding Woods Dr, Oakville without a car, you can get around rather easily. The closest transit stop is a Bus Stop (River Oaks Blvd West / Winding Woods Dr) and is a short distance away connecting you to Oakville's public transit service. It also has route River Oaks Express nearby.