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2203 Winding Woods Drive in Oakville for sale

Asking price
$2,199,000
Estimate (Sep 17)
$2,064,828
MLS #:
W13797086
Type:
Detached, 2-Storey
Approx. SQFT:
3500-5000
Basement:
Finished
4 4
2 57.55 x 137.43 ft lot
PROPERTY HISTORY
SIGN IN REQUIRED
List Date List Price Last Status Sold Date Sold Price Days On Market
0000-00-00 $00000 Ter N/A N/A N/A
0000-00-00 $00000 Ter N/A N/A N/A
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.

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  • Date Listed: Thursday, September 17, 2026
  • Listing Brokerage: Re/Max Escarpment Realty Inc. - Disclaimer: The information contained in this listing has not been verified by Re/Max Escarpment Realty Inc. and should be verified by the buyer.
  • Virtual Tour: View Virtual Tour for 2203 Winding Woods Drive
  • City: Oakville

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  • Neighbourhood: River Oaks
  • Major Intersection: River Oaks Blvd/Winding Woods
  • Full Address: 2203 Winding Woods Drive, Oakville, L6H 5T9, Canada, ON, Canada
  • Kitchen:
  • Family Room:
  • Living Room:
  • Amenities:
  • Taxes: $11,070.00 (2026)
Breakfast22 x 10 ft220 sq ft
Kitchen13 x 26 ft338 sq ft
Dining12 x 19 ft228 sq ft
Family20 x 13 ft260 sq ft
Living18 x 13 ft234 sq ft
Primary29 x 20 ft580 sq ft
2nd Br13 x 12 ft156 sq ft
3rd Br17 x 13 ft221 sq ft
4th Br16 x 13 ft208 sq ft
Den18 x 12 ft216 sq ft
Rec45 x 23 ft1035 sq ft
Office21 x 10 ft210 sq ft
Utility24 x 13 ft312 sq ft
  • Sunday - October 04 2:00 - 4:00 PM

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