2203 Winding Woods Drive

ActiveOakville · 1015 - RO River Oaks65 days on marketMLS® W13227366

$2,399,000

$685 / sq ft

Bedrooms4

Bathrooms5

Interior3,500 sq ft

TypeSingle Family Home

ListingFor Sale

Days on Market65

About this property

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' 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.

Features & finishes

View

Fireplace

Air Conditioning

Basement

Property details

MLS® Number	W13227366
Status	Active
Listing Type	For Sale
Property Type	Single Family Home
Interior Size	3,500 sq ft
Beds / Baths	4 bed · 5 bath
Neighbourhood	1015 - RO River Oaks
City	Oakville
Postal Code	L6H 5T9
Province	ON
Listed Date	June 2, 2026
Days on Market	65
Price per Sq Ft	$685
Brokerage	RE/MAX ESCARPMENT REALTY INC.