2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
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2203 Winding Woods Drive
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2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
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2203 Winding Woods Drive
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2203 Winding Woods Drive
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50 photos

2203 Winding Woods Drive

River Oaks, Oakville, ON
Listed 25 days ago
$2,399,000For Sale
$2,076,576Estimated value
4Bedrooms
5Bathrooms
3500-5000 sqftSize
6 (2 garage)Parking
58 ft × 137 ftLot Size
DetachedProperty Type

2203 Winding Woods Drive

Oakville, ON · River Oaks

Listed 25 days ago
Bedrooms4
Bathrooms5
Size3500-5000 sqft
Parking6 (2 garage)
Lot Size58 ft × 137 ft
Property TypeDetached
$2,399,000
For Sale
MLS# W13227366
$2,076,576Estimated value

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About this home

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 fun…

Features & Details

Property Type
Detached
Tax
$11,070 / 2026
Size
3500-5000 sqft
Lot Size
57.55 x 137.43 Feet
Basement Info
Finished
Total Parking Spaces
6 (2 Garage)
Title
Residential Freehold
Property Style
2-Storey
Community
River Oaks
Municipality
Oakville
Construction
Brick
Cross Street
River Oaks Blvd/Winding Woods
Front Door Facing
East
Local Amenities
Electric Car Charger, Hospital, Park, Golf, Rec./Commun.Centre, Wooded/Treed
Lot Legal Description
PCL40-1, SEC 20M531; LT 40, Plan M531, Oakville
Data Source
Toronto Regional Real Estate Board
Brokerage
RE/MAX ESCARPMENT REALTY INC.
Listed On
Jun 02, 2026
Listing Expires On
Nov 30, 2026
Listing Updated On
Jun 02, 2026
Bedrooms
4
Bathrooms
5
Kitchens
1
Rooms
9
Bathroom Detail
2 Pcs on Main Level
Bathroom Detail
3 Pcs on 2nd Level
Bathroom Detail
4 Pcs on 2nd Level
Bathroom Detail
5 Pcs on 2nd Level
Bathroom Detail
2 Pcs on Basement Level
Garage Type
Attached
Garage
2
Parking
6
Heating
Forced Air
Heat Source
Gas
Cooling
Central Air
Sewer
Sewer
Den / Family Room
Yes
Fireplace
Yes
Swimming Pool
None
Roof Material
Asphalt Shingle
Foundation Type
Unknown
Interior Features
Auto Garage Door Remote, Central Vacuum

Listing History

Active25 days on marketCurrently viewingMLS #W13227366
Jun 2, 202626 days ago
Listed for Sale
Sign in to view
Terminated32 days on marketMLS #W13064222
Jun 2, 202626 days ago
Terminated
Sign in to view
Apr 30, 20261 month ago
Listed for Sale
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Estimate History

Estimated value, last 24 months
Jul 2024 – Jun 2026
$2.19M
$2.02M
$1.86M
$1.69M
Jul
Dec
May
Oct
Mar
Jun

Automated estimate from Polsinello Predictive AI. Not an appraisal. Actual market value may differ.

Mortgage calculator

Estimated monthly payment
$11,703

Estimated payment. Does not include property tax, insurance, or condo fees.

Location & nearby

River Oaks Real Estate Market

Oakville · last 90 days
$1,465,000
Median sold price
+38.5%
Median price, year over year
32 days
Avg days on market
64
Homes sold (90 days)
14%
Sold above asking
83%
Sold below asking
$556–$705/ft²
Price per sq ft
Median price trend
Jun 2025 – Jun 2026
$1.62M
$1.41M
$1.21M
$1M
Jun
Sep
Dec
Mar
Jun

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(905) 830-9111