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2203 Winding Woods Drive — Photo 11 / 50

$2,549,000

2203 Winding Woods Drive

1015 - RO River Oaks · Detached

4

Beds

5

Baths

3500-5000

Sqft

6

Parking

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

TypeDetached
Community1015 - RO River Oaks
MunicipalityOakville
ListedApr 30, 2026
StatusCancelled
MLS#W13064222

Inside

Bedrooms4
Bathrooms5

Building

Size3500-5000 sqft

Parking

Total Parking6

Room Sizes

Main Level

Breakfast21.9' x 9.9'
Kitchen12.8' x 25.9'
Dining Room12.0' x 19.3'
Family Room19.9' x 13.5'
Living Room17.9' x 12.8'

Upper Level

Primary Bedroom29.3' x 19.9'
Bedroom 213.0' x 12.0'
Bedroom 316.6' x 13.1'
Bedroom 415.9' x 12.9'
Den18.1' x 12.0'

Basement

Recreation45.2' x 22.6'
Office21.4' x 10.4'
Utility Room24.5' x 12.9'

Sale History

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Area Stats

1015 - RO River Oaks · Last 90 days

Sales

$1,130,000

Median Price

38

Avg DOM

102

Sold

Leases

$2,550

Median Rent

31

Avg DOM

145

Leased

Listed by RE/MAX ESCARPMENT REALTY INC.

Quick details

Price$2,549,000
TypeDetached
TransactionFor Sale
StatusCancelled
MLS#W13064222
Beds4
Baths5
Size3500-5000 sqft

Zoned Schools

Elementary

Secondary