2203 Winding Woods Drive, Oakville, ON L6H 5T9, Oakville, ON
Bed 4
Bath 5
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.
Property Highlights
For Sale
MLS NO.
W13064222
Type
Residential Freehold
Sub Type
Detached
Bedrooms
4
Bathrooms
5
Parking
6.0
Garage
Yes
Complete Property Details
Property Type
Residential Freehold
Sub Type
Detached
Transaction Type
For Sale
Status
Cancelled
Contract Status
Unavailable
MLS® Number
W13064222
Living Area Range
3500-5000
Total Bedrooms
4
Bedrooms Above Grade
4
Total Bathrooms
5
Total Kitchens
1
Kitchens Above Grade
1
Rooms Above Grade
9
Rooms Below Grade
2
Interior Features
Auto Garage Door Remote, Central Vacuum
Fireplace
Yes
Central Vacuum Yn
Yes
Construction
Brick
Roof
Asphalt Shingle
Lot Width
57.55
Parking Total
6.0
Covered Spaces
2.0
Garage Type
Attached
Garage
Yes
Pool
None
Direction Facing
East
Cooling
Central Air
Heat Source
Gas
Heat Type
Forced Air
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
2203 Winding Woods Drive, Oakville, ON L6H 5T9
City
Oakville
Neighbourhood
1015 - RO River Oaks
County / Region
Halton
Province / State
ON
Postal Code
L6H 5T9
Cross Street
River Oaks Blvd/Winding Woods
Directions
River Oaks Blvd/Winding Woods
Country
CA
List Price
$2,549,000
Annual Taxes
$10,858
Tax Year
2025
Legal Description
PCL40-1, SEC 20M531; LT 40, Plan M531, Oakville
Possession Type
Flexible
Possession Details
Flexible
Listing Office
RE/MAX ESCARPMENT REALTY INC.
Board
Toronto Regional Real Estate Board
Original Entry
2026-04-30T17:37:06Z
Media Updated
2026-04-30T17:48:41Z
Photos Updated
2026-04-30T17:37:07Z
Last Modified
2026-06-02T13:58:36Z
System Modified
2026-07-06T21:31:17.57103Z
MLS Status
Terminated
Architectural Style
2-Storey
Basement
Finished
Ddfyn
Yes
Expiration Date
2026-10-30
Foundation Details
Unknown
Heat Source Multi
Gas, Wood
Heat Type Multi
Forced Air
Hstapplication
Included In
Link Yn
No
Occupant Type
Owner
Originating System Id
A00001796
Parcel Number
250640043
Parking Spaces
4
Property Features
Electric Car Charger, Hospital, Park, Golf, Rec./Commun.Centre, Wooded/Treed
Public Remarks
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.
