2203 Winding Woods Drive, Oakville, ON L6H 5T9
- Property tax
- $11,070 / year
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.
- MLS number
- W13227366
- Type
- Detached
- Status
- Active
- Bedrooms
- 4
- Bathrooms
- 5
- Postal code
- L6H 5T9
- Photos
- 50
- Laundry
- Main Level level
This listing’s own days on market are shown above. How long the property has been for sale across every earlier listing is drawn from records the board releases only to registered users — a free account opens it, along with the sale history below.
Rooms
13 rooms as the listing brokerage filed them, with measurements.
Main
| Room | Size | Features |
|---|---|---|
| Breakfast | 6.68 × 3.03 m | — |
| Kitchen | 3.89 × 7.89 m | — |
| Dining Room | 3.65 × 5.89 m | — |
| Family Room | 6.08 × 4.11 m | — |
| Living Room | 5.47 × 3.89 m | — |
Second
| Room | Size | Features |
|---|---|---|
| Primary Bedroom | 8.93 × 6.06 m | — |
| Bedroom 2 | 3.95 × 3.66 m | — |
| Bedroom 3 | 5.06 × 3.98 m | — |
| Bedroom 4 | 4.84 × 3.94 m | — |
| Den | 5.51 × 3.66 m | — |
Basement
| Room | Size | Features |
|---|---|---|
| Recreation | 13.78 × 6.90 m | — |
| Office | 6.53 × 3.18 m | — |
| Utility Room | 7.46 × 3.94 m | — |
Property details
As filed by the listing brokerage. Anything the board left blank is left out rather than shown as unknown — and none of it is guaranteed accurate by PropTx, so verify what you rely on.
Property
- Type
- Detached
- Style
- 2-Storey
- Class
- Residential Freehold
- Fronting on
- East
- Community
- 1015 - RO River Oaks
- Municipality
- Oakville
- Cross street
- River Oaks Blvd/Winding Woods
- Zoning
- RL5
Inside
- Bedrooms
- 4
- Bedrooms above grade
- 4
- Bathrooms
- 5
- Washrooms
- 1 on the main floor · 1 on the second floor · 1 on the second floor
- Kitchens
- 1
- Rooms above grade
- 9
- Family room
- Yes
- Fireplace
- Yes
- Fireplaces
- 2
- Basement
- Finished
- Laundry
- Main Level
- Size
- 3500-5000
Building
- Construction
- Brick
- Roof
- Asphalt Shingle
- Foundation
- Unknown
- Other structures
- Shed
Parking
- Garage
- Attached
- Covered spaces
- 2
- Driveway spaces
- 4
- Total parking
- 6
Land
- Lot
- 57.55 × 137.43 feet
- Shape
- Irregular
- Pool
- None
Heating, cooling and services
- Heating
- Forced Air
- Heat source
- Gas
- Cooling
- Central Air
- Water
- Municipal
- Sewer
- Sewer
Features
- Property
- Electric Car Charger, Hospital, Park, Golf, Rec./Commun.Centre, Wooded/Treed
- Interior
- Auto Garage Door Remote, Central Vacuum
- Exterior
- Lawn Sprinkler System, Landscape Lighting
Listing
- MLS number
- W13227366
- Status
- New
- Previous status
- Draft
- Listed on
- 2026-06-02
- Expires
- 2026-11-30
- Taxes
- $11,070 (2026)
- Board
- Toronto Regional Real Estate Board
Listing history
This address has been listed 2 times.
Where this property is
Where this address sits, matched against open government data.
Matched to a published address point for this address.
Schools
The school boundaries this address is inside, and the schools nearest it. Boards redraw boundaries and cap programs — confirm with the board before this affects a decision.
Other schools nearby
By distance from this address, not school boundary — a school 400 m away can be in another school’s attendance area.
| School | Level | Distance | Rating |
|---|---|---|---|
| Rotherglen School - Oakville Elementary | Elementary and secondary | 425 m | Not reported |
| River Oaks Public School Halton DSB | Elementary | 411 m | / 10 70% met the standard |
| Holy Trinity Catholic Secondary School Halton CDSB | Secondary | 1.0 km | / 10 79% met the standard · 2 of 6 measures |
| Our Lady of Peace Catholic Elementary School Halton CDSB | Elementary | 850 m | / 10 89% met the standard |
| St. Andrew Catholic Elementary School Halton CDSB | Elementary | 1.5 km | / 10 80% met the standard |
| Rotherglen School Meadowvale Campus | Elementary | 1.2 km | Not reported |
How the rating is calculated
EQAO — Ontario’s testing agency — publishes, for each school, the percentage of students meeting the provincial standard in Grade 3 and Grade 6 reading, writing and mathematics. The rating is the average of those percentages divided by ten. A school where 72% of students met the standard rates 7.2 out of 10.
Nothing is weighted or adjusted, and schools are not ranked against each other. Where EQAO withholds a result to protect the privacy of a small group of students, that measure is left out rather than counted as zero — so a rating built on fewer than six measures says so.
What it does not measure. It is one year of standardised testing in three subjects. It says nothing about teaching, programs, or whether a school suits a particular child, and it tracks neighbourhood household income closely enough that it partly measures the neighbourhood rather than the school. Treat it as one figure among many.
Source: Ontario Ministry of Education, School Information and Student Demographics (2024–25), Open Government Licence – Ontario.
H-Value
What an H-Value is and how it is calculated — the method and our measured error, no account needed.
The market around this home
Detached houses in 1015 - RO River Oaks — 200 sales over the last five years.
How these are built, and what they cannot tell you
Each point is the median of the sales that closed in that quarter among detached houses in 1015 - ro river oaks. A quarter with fewer than eight is left out rather than drawn, and the line breaks where that happens — a median over three sales is really one home’s price, and joining across a gap would draw a number nobody measured.
This is not an estimate of what this home is worth. The segment is a property type in an area; it takes no account of this home’s size, condition, renovations, lot, exposure or how it compares to its neighbours, and half the homes in any quarter sold for more than the median and half for less. It is context for a conversation with an agent, not a valuation.
Toronto Regional Real Estate Board closed transactions. Deemed reliable but not guaranteed accurate by PropTx.
This neighbourhood
Statistics Canada 2021 Census, for the surrounding few blocks — about 381 people.
The neighbourhood, by the census
Statistics Canada 2021 Census for dissemination area 35240620 — the few blocks around this address, home to 381 people. It describes the area, not this property.
Percentages are of the 190 responses in this category. Statistics Canada rounds counts and withholds small ones to keep individuals unidentifiable, so categories with too few people to publish are absent rather than shown as zero.
Source: Statistics Canada, 2021 Census of Population. Contains information licensed under the Open Government Licence – Canada.
Work out the numbers
Everything below is calculated in your browser from figures you can change. Nothing is sent anywhere.
If you rented it out
How this is calculated, and what it leaves out
Canadian fixed-rate mortgages compound semi-annually, not monthly, so the monthly rate here is (1 + rate/2)1/6 − 1. Most calculators use rate ÷ 12, which is the American convention and overstates the payment by tens of dollars a month.
Below 20% down, default insurance is mandatory and is added to the loan rather than paid at closing: 2.80% at 85% loan-to-value, 3.10% at 90%, 4.00% at 95%. It is unavailable at or above $1.5M, which is why 20% is a hard floor there.
Not included: vacancy, property management, capital repairs, income tax, and the fact that a lender qualifies you at a stress-test rate rather than the one you are quoted. This is arithmetic on the numbers above, not a mortgage approval or an opinion of what you can afford.