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2203 Winding Woods Drive
Sun, Nov 8 · 2:00 to 4:00 PM
Listing courtesy of RE/MAX ESCARPMENT REALTY INC. · MLS® W13797086
About this home
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.
My take · Jai Mession
How this home sits in today's market
This is priced in the middle of what is for sale nearby, so the details decide it: the lot, the light, the street and the work done since it was built. It has been listed for 49 days, which usually means there is room to talk.
Want my value range on this home?
I will compare it with what actually sold nearby, not just what is asking, and send you my number.
Counted from today's live listings in Oakville. Asking prices, not sold prices, and not an appraisal.

Jai Mession, Salesperson, The Agency, Brokerage · 31 Scarsdale Rd, Unit 6, North York, ON M3B 3R8 · 416 847 5288 · 647 887 9867. This website is operated by a salesperson who is a member of The Canadian Real Estate Association. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Listing information from CREA's DDF®, believed reliable but not guaranteed. Terms of use.