2203 Winding Woods Drive, Oakville, ON L6H 5T9

Uptown Core>2203 Winding Woods Drive, Oakville, ON L6H 5T9

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4 bed

5 bath

6parking

sqft *

NewJust Listed

List Price:

$2,549,000

Listed on May 2026

416 837 2000/647 929 9072

info@tjanjua.com

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Listing History

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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.

Extras

Details

Area	Halton
Family Room	Yes
Heat Type	Forced Air
A/C	Central Air
Garage	Attached
Neighbourhood	1015 - RO River Oaks

Fireplace	2
Heating Source	Gas
Sewers	Sewer
Laundry Level
Pool Features	None

Rooms

Room	Dimensions	Features
Utility Room (Basement)	7.46 X 3.94 m
Office (Basement)	6.53 X 3.18 m
Recreation (Basement)	13.78 X 6.9 m
Den (Second)	5.51 X 3.66 m
Bedroom 4 (Second)	4.84 X 3.94 m
Bedroom 3 (Second)	5.06 X 3.98 m
Bedroom 2 (Second)	3.95 X 3.66 m
Primary Bedroom (Second)	8.93 X 6.06 m
Living Room (Main)	5.47 X 3.89 m
Family Room (Main)	6.08 X 4.11 m
Dining Room (Main)	3.65 X 5.89 m
Kitchen (Main)	3.89 X 7.89 m
Breakfast (Main)	6.68 X 3.03 m

Broker: RE/MAX ESCARPMENT REALTY INC.MLS®#: W13064222

Population

Gender

male

female

45%

55%

Family Status

> 15 Married with Childrn 5%

> 15 Single with Children 8%

Marital Status

Age Distibution

Dominant Language

Immigration Status

Socio-Economic

Employment

Highest Level of Education

Households

Structural Details

Total # of Occupied Private Dwellings930

Dominant Year BuiltNaN

Ownership

Owned

Rented

48%

52%

Age of Home (Years)

Structural Type