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$2,549,000
New Listing

2203 Winding Woods Drive
Oakville, ON L6H 5T9

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
3500-5000
SqFt

/SqFt
County:
Halton
2203 Winding Woods Drive2203 Winding Woods Drive2203 Winding Woods Drive2203 Winding Woods Drive
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Monthly Payment (Est.)

$11,630
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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 ft 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.

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Listing Snapshot
Price 
$2,549,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
3500-5000 sqft
Total Baths 
5
Full Baths 
N/A
Partial Baths 
N/A
Lot Size 
57.48x137.22 Acres
Year Built 
N/A
MLS® Number 
W13064222
Status 
Active
Property Tax 
$10,858
Maintenance Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
4 hours agoListing updated with changes from the MLS®
4 hours agoListing first seen on site
General Features
Attached Garage 
Yes
Cross Street 
River Oaks Blvd/Winding Woods
Direction Faces 
East
Garage 
Yes
Number Of Stories 
2
Parking 
Garage Door OpenerAttached
Parking Spaces 
6
Property Sub Type 
Single Family Residence
Style 
2-Storey
Interior Features
Basement 
Finished
Cooling 
Central Air
Fireplace 
Yes
Heating 
Natural GasForced Air
Interior 
Central Vacuum
Bedroom 2 
Dimensions - 3.95 x 3.66Level - Second
Bedroom 3 
Dimensions - 5.06 x 3.98Level - Second
Bedroom 4 
Dimensions - 4.84 x 3.94Level - Second
Breakfast 
Dimensions - 6.68 x 3.03Level - Main
Den 
Dimensions - 5.51 x 3.66Level - Second
Dining Room 
Dimensions - 3.65 x 5.89Level - Main
Family Room 
Dimensions - 6.08 x 4.11Level - Main
Kitchen 
Dimensions - 3.89 x 7.89Level - Main
Living Room 
Dimensions - 5.47 x 3.89Level - Main
Master Bedroom 
Dimensions - 8.93 x 6.06Level - Second
Office 
Dimensions - 6.53 x 3.18Level - Basement
Recreation 
Dimensions - 13.78 x 6.9Level - Basement
Utility Room 
Dimensions - 7.46 x 3.94Level - Basement
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Exterior Features
Construction Details 
Brick
Lot Features 
On Golf CourseWooded
Other Structures 
Shed(s)
Pool Features 
None
Roof 
Asphalt
Listing courtesy of RE/MAX ESCARPMENT REALTY INC.

Listing information is provided by Participants of the Toronto Real Estate Board. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2026, Toronto Real Estate Board
Last checked 2026-04-30 09:23 PM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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