2203 Winding Woods Drive, Oakville, ON L6H 5T9
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.
Breakfast
6.68 x 3.03
Main
Kitchen
3.89 x 7.89
Main
Dining Room
3.65 x 5.89
Main
Family Room
6.08 x 4.11
Main
Living Room
5.47 x 3.89
Main
Primary Bedroom
8.93 x 6.06
Second
Bedroom 2
3.95 x 3.66
Second
Bedroom 3
5.06 x 3.98
Second
Bedroom 4
4.84 x 3.94
Second
Den
5.51 x 3.66
Second
Recreation
13.78 x 6.9
Basement
Office
6.53 x 3.18
Basement
Utility Room
7.46 x 3.94
Basement
Interior features
Auto Garage Door Remote, Central Vacuum
Basement
Finished
Bathrooms
1 × 2-piece — Main, 1 × 3-piece — Second, 1 × 4-piece — Second, 1 × 5-piece — Second, 1 × 2-piece — Basement
Fireplace
Yes
Family room
Yes
Kitchens
1
Rooms (above / below grade)
9 above, 2 below
Architectural style
2-Storey
Construction materials
Brick
Roof
Asphalt Shingle
Exterior features
Lawn Sprinkler System, Landscape Lighting, Backs On Green Belt
Direction faces
East
Garage type
Attached
Garage spaces
2
Total parking spaces
6
Driveway parking
4
Parking features
Private
Lot size
57.55 x 137.43 ft
Cross street
River Oaks Blvd/Winding Woods
Directions
River Oaks Blvd/Winding Woods
Neighbourhood
1015 - RO River Oaks
Heating
Forced Air — Gas, Wood
Cooling
Central Air
Water
Sewer
Sewer
List price
$2,199,000
Original list price
Annual taxes
$11,070
Tax year
2026
Legal description
PCL40-1, SEC 20M531; LT 40, Plan M531, Oakville
Inclusions
Exclusions
MLS #
W13797086
Status
Active
Transaction type
For Sale
Property type
Residential Freehold
Property sub type
Detached
Days on market
List date
Possession
Flexible
Occupancy
Owner
Listing brokerage
RE/MAX ESCARPMENT REALTY INC.
$1,694,000
Median list price
26
Active listings
New in last 30 days
Median days on market
Estimated monthly payment
$10,542
Educational estimate only — actual payment depends on your lender, credit, and insurance requirements.
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