Full and half bathrooms as the listing totals them.
Interior area
3,500 to 5,000 sqft
A band, not a measurement. Interior area as the listing states it. It does not say whether the figure was measured on site or taken from builder plans.
Property type
Detached
Style as listed: 2-Storey.
Second dwelling
The listing does not say whether there is a second dwelling unit here. Other records in this set state it either way, so this is a silence rather than a no.
Counts and measurements as the listing states them, not verified by us. MLSSource: MLS
$2.4MFor Sale
2203 Winding Woods Drive, Oakville, ON · 4 bed · 5 bath · 4,250 sqft
Three parties produce a dollar figure for this house, for three different purposes, so they do not agree and were never meant to. The gaps are worked out here rather than left for you to hold in your head.
Asking price
$2,399,000
Set by the seller and their brokerage. It is a request, and nothing tests it until an offer arrives.
MLSSource: MLS
Our estimate
Not licensedOur estimate: Not shown: our current listing agreement does not licence this figure for display.
Modelled from comparable sales by the explorer further down this page. Change the comparables there and this number moves, which is the reason it is shown at all.
Est.Modelled from comparable sales, not an appraisal
Assessed value, 2026
Nothing of this kind on the record, and nothing here fills it in from an average of other houses.
The figure property tax is apportioned from, valued as of a date that is not today. It is not a market value and no lender treats it as one.
MLSMunicipal assessment and tax roll
Price per square foot
$564
asking price over 4,250 sqft, an area the listing does not source
Days on market
N/A
no area average shown: our current listing agreement does not licence market statistics
None of these is an appraisal. Your lender orders one of those once an offer is accepted, and it is the figure that decides how much they will actually lend.
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.
Written by the listing brokerage to sell the house. Nothing in it is verified, so take its claims about condition to an inspection, not from it.
Nest 360 estimate
Our estimate for this listing is not shown here
Not shown: our current listing agreement does not licence this figure for display.
The estimate is built by weighing recent comparable sales, and sold comparables for a specific property are licensed to registered users only. It is withheld rather than approximated: an estimate with the sales taken out of it would be a number with nothing behind it.
Price and listing history
This listing's price and status history is not shown here
Not shown: our current listing agreement does not licence this figure for display.
Prior asking prices, terminations and relists are licensed to registered users only, and there are no accounts on Nest 360 yet. Nothing here should be read as evidence that the current price is the only price this house has been offered at.
Property details
MLSSource: MLS
Type
Detached
Style
2-Storey
Bedrooms
4
Bathrooms
5
Kitchens
1
Living area
3,500 to 5,000 sqft
Lot size
58 by 137 ft
Status
For Sale
Occupancy
Owner occupied
Features
MLSSource: MLS
The pills are copied from the listing and sorted for reading, with nothing added to them, and a group the listing did not fill in is absent rather than empty. Where a group is written as sentences instead, those are ours: what the listing named, and what it means.
Outside
Lawn Sprinkler System
Landscape Lighting
None pool
Interior finishes
Auto Garage Door Remote
Also listed
On the record, and not one of the groups above.
Central Vacuum
Interior and systems
MLSSource: MLS
Heating
Forced Air · Gas
Cooling
Central Air
Basement
Finished
Construction
Brick
Roof
Asphalt Shingle
Foundation
Unknown
Sewer
Sewer
Parking and exterior
MLSSource: MLS
Garage spaces
2
Driveway spaces
4
Total parking
6
Pool
None
Exterior features
Lawn Sprinkler System, Landscape Lighting
Taxes and assessment
MLSMunicipal assessment and tax roll
Assessment year
2026
Annual property tax
$11,070
Tax year
2026
Property tax by year
MLSSource: MLS
1 years · latest $11,070
1 years, from $11,070 in 2026 to $11,070 in 2026.
Location and neighbourhood
MLSSource: MLS
Market trend
Neighbourhood market statistics is not shown here
Not shown: our current listing agreement does not licence this figure for display.
Medians, sale-to-list ratios and absorption are computed from sold prices, and they are licensed to registered users only. There is no approximate version of a median that would be honest to show in their place.
