2203 Winding Woods Drive — photo 11 / 50

$2,199,000

2203 Winding Woods Drive

RO River Oaks, Oakville, ON

4

Bedrooms

5

Bathrooms

3500-5000

Sq Ft

6

Parking

Open House

  • Sunday, September 20 · 2:00 p.m.4:00 p.m.

About this property

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.

Property details

MLS® Number
W13797086
Property Type
Detached
Style
2-Storey
Lot Size
57.55 × 137.43 feet
Garage
Attached
Basement
Finished
Heating
Forced Air
Cooling
Central Air
Annual Taxes
$11,070
Listed
September 17, 2026
Brokerage
RE/MAX ESCARPMENT REALTY INC.

No obligation

15-Minute Real Estate Consultation

Talk through your goals, timeline and next steps with Stephen Rochester — buying, selling, investing or a specific property.

Listing data is provided through our authorized MLS® feed and is deemed reliable but not guaranteed. Information is refreshed regularly and may change without notice — contact Stephen to confirm current availability.

Powered by REALTOR.ca — MLS®, REALTOR® and associated logos are trademarks owned by The Canadian Real Estate Association (CREA), identifying real estate professionals who are members of CREA.

View this listing on REALTOR.ca

Similar homes

584 Weynway Court, Oakville
New

$2,399,000

584 Weynway Court

WO West, Oakville

6 Beds 5 Baths 3000-3500 sq ft

Detached

View Property

MLS® W13797370 · ROYAL LEPAGE REAL ESTATE SERVICES LTD.

204 Mary Street, Oakville
New

$1,849,000

204 Mary Street

CO Central, Oakville

4 Beds 3 Baths 3000-3500 sq ft

Detached

View Property

MLS® W13797354 · CITYSCAPE REAL ESTATE LTD.