$2,399,000
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2203 Winding Woods Drive, Oakville (ro River Oaks), ON L6H5T9

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4 Beds
5 Baths
- Sq Ft

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. (id:58753)

Listing By: Melissa Cescon - RE/MAX ESCARPMENT REALTY INC. cncrea2 Realty.com
  • MLS® W13227366
  • Date Listed06/02/2026
  • Days on Realty 6 Days
  • Bedrooms 4
  • Bathrooms 5 baths
  • Lot Size -
  • Sewer Other
  • Property Type Single Family Residence
  • Water Public

Interior Features

  • Appliances Central Vacuum, Garage door opener remote(s)
  • Cooling Central air conditioning
  • Heating Forced air, Natural gas, Wood

Exterior / Lot Features

  • Roof -
  • Lot Size Acres -
  • Lot Size SQFT -
  • Lot Features Wooded area, Irregular lot size

Directions

Cross Streets: River Oaks Blvd/Winding Woods. ** Directions: River Oaks/Winding Woods.

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for L6H5T9

Discover key demographics, population statistics, and environmental insights for the Oakville (ro River Oaks), ON area.

Walkability in ON / L6H5T9

Source: Walk Score

19/100

Car-Dependent

Walk Score ®

38/100

Some Transit

Transit Score ®

65/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. A few nearby public transportation options. Some bike infrastructure.

Transit Summary

12 nearby routes: 12 bus, 0 rail, 0 other

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 32/100, Transit Score: 38/100, Bike Score: 49/100.

Points of Interest near 2203 WINDING WOODS DRIVE, Oakville (RO River Oaks), ON L6H5T9

Frequently Asked Questions for 2203 WINDING WOODS DRIVE

Source: Realty.com

2203 WINDING WOODS DRIVE, Oakville (RO River Oaks), ON L6H5T9 in Oakville (RO River Oaks), ON L6H5T9 is a single family residence listed at $2,399,000. Highlights include 4 bedrooms, 5 bathrooms. Realty.ca has 50 photos, sales history, school insights, and mortgage tools for this listing.

Realty.com has 50 photos of 2203 WINDING WOODS DRIVE.

The full address for this home is 2203 WINDING WOODS DRIVE, Oakville (RO River Oaks), ON L6H5T9.

2203 WINDING WOODS DRIVE has been listed on Realty.com since Tue June 02, 2026

Almost all errands require a car. A few nearby public transportation options. Some bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 32/100, Transit Score: 38/100, Bike Score: 49/100.

Listing provided courtesy of: RE/MAX ESCARPMENT REALTY INC.
Listing agent: Melissa Cescon

This content last refreshed on 2026-06-08 13:00:10. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.