43.4632° N · 79.7266° W — River Oaks, Oakville — MLS® #W13797086
2203 Winding Woods Dr
$2,199,000
River Oaks, Oakville, Ontario L6H 5T9
- 4
- BedroomsBeds
- 5
- BathroomsBaths
- 3500-5000 sqft3500-5000
- SizeSq ft
- 57.55 x 137.43 ft
- Lot sizeLot
Inquire about this listing
In short · from the listing record
2203 Winding Woods Dr is a 4-bedroom, 5-bathroom detached house in River Oaks, Oakville, listed for sale at an asking price of $2,199,000 (MLS® W13797086).
Luxury Living set on one of River Oaks' most coveted streets! This residence is completely immersed in nature, with forest and walking paths wrapping the rear and south side, and a ravine beyond, the setting is incredibly private. Offering over 4,200 sq. ft. above grade and 6,000 sq. ft. of total 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 private lifestyle, inviting, and truly a rare opportunity.
Listing readings
How it measures up
Scores from the listing record and the market around it.
73Good
Condition score
1 documented update signal
Listing age, structured features and disclosed update language; not an inspection.
5Shortfall
Cash flow quality
−$6,856/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Median of 5 homes with 4 bedrooms for lease in River Oaks right now. Cost of owning counts the mortgage and property tax.
Condition uses listing-record signals, not an inspection.
The data table
Every fact
Everything the board publishes for this home.
- Tax
- $11,070 / 2026
- MLS® number
- W13797086
- Board
- TRREB MLS®
- Property Type
- Detached
- Time on market
- Size
- 3500-5000 sqft
- Lot Size
- 57.55 x 137.43 ft
- Listed on
- Parking
- 2 Attached, 6 Parking
Listing history
Listing activity for 2203 Winding Woods Dr, Oakville, Ontario
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $2,199,000 | N/A | For Sale | W13797086 |
Inside
Room by room
From the listing.
- Breakfast3.03 × 6.68 m
- Kitchen7.89 × 3.89 m
- Dining5.89 × 3.65 m
- Family4.11 × 6.08 m
- Living3.89 × 5.47 m
- Primary6.06 × 8.93 m
- 2nd Br3.66 × 3.95 m
- 3rd Br3.98 × 5.06 m
- 4th Br3.94 × 4.84 m
- Den3.66 × 5.51 m
- Rec6.9 × 13.78 m
- Office3.18 × 6.53 m
- Utility3.94 × 7.46 m
Property
- Property Type
- Detached
- Style
- 2-Storey
- Community
- River Oaks
- Municipality
- Oakville
Building
- Size
- 3500-5000 sqft
- Construction
- Brick
Inside
- Bedrooms
- 4
- Bathrooms
- 5
- Bathroom Details
- 1 × 2pc Main, 1 × 3pc 2nd, 1 × 4pc 2nd, 1 × 5pc 2nd, 1 × 2pc Bsmt
- Basement Type
- Finished
- Kitchens
- 1
Parking
- Driveway
- Private
- Garage Type
- Attached
- Garage
- 2
- Additional Parking
- 4
- Total Parking
- 6
Utilities
- Water
- Municipal
- Cooling
- Central Air
- Heating Type
- Forced Air
Land
- Sewer
- Sewers
- Frontage
- 57.55 ft
- Depth
- 137.43 ft
- Lot Size
- 57.55 x 137.43 ft
Where it sits
The street and the area
Asking prices on the map.
Map and tour
Transit nearby
| Station | Lines | Distance |
|---|---|---|
| Oakville GO | GO Transit train: Lakeshore West | 3.7 km |
The nearest subway, light rail, train, bus rapid transit stations 5 km, as the crow flies. Source: GO Transit schedule data (GTFS) from Metrolinx under the Open Government Licence – Ontario – Metrolinx, downloaded October 18, 2026. Data used in this product or service is provided with the permission of Metrolinx. Metrolinx makes no representations or warranties of any kind, express or implied, with respect to the Data and assumes no responsibility for the accuracy or currency of the data used in this product or service. Contains information licensed under the Open Government Licence – Ontario – Metrolinx.
Around it
Detached in River Oaks
Active listings only, today.
Detached homes for sale in River Oaks right now
- For sale now
- 25
- Median asking price
- $1.73M
- New in 7 days
- 2
- Price cuts
- 28%
Middle half: $1.46M to $2.1M
9 in 28 days
7 listings
This home is asking 27% above the median, higher than three quarters of them.
See all homes in River OaksAsking prices and counts of the MLS® listings on this site as of today. Asking figures only, never sold or leased prices.
Site report
What the record says
What the City and the conservation authority have on file for this address.
- provincial plansNone in rangeOutside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areas
- wetlandNone in rangeNo mapped wetland within 120 m
- aggregateNone in rangeNo licensed pit or quarry within 2 km
- wellsNone in rangeNo recorded oil, gas or salt well within 250 m
- transitOn recordTransit stop within 400 m From the transit agency’s published stop map; the nearest is 150 m away. Routes and stops change; check the agency’s schedule.
- trailOn recordA trail on the Ontario trail network within 1 km
- airportOn recordNearest airport: 9.9 km
- water wellsNone in rangeNo water-supply well recorded within 250 m
- npriNone in rangeNo facility within 1 km reports pollutant releases to Environment Canada Only facilities above the inventory’s reporting thresholds are listed.
- fcsiNone in rangeNo federal contaminated site within 1 km The federal inventory covers federal land only; it says nothing about provincial or private sites.
- electricityOn recordElectricity is distributed here by Oakville Hydro Electricity Distribution Inc.
- internet speedOn recordWired internet 50/10 Mbps or faster is listed at this location Fixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (20 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.
- broadbandOn recordAcross the surrounding area: fibre to the home, cable, DSL internet listed Fibre to the home: Bell, CIK Telecom, Cogeco Connexion, Rogers. Cable: Cogeco Connexion. DSL: Bell. Fixed wireless: Bell, QuaenetFi, Rogers, Routcom, SkyChoice Communications, Standard Broadband. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.
Each record is the map at the home’s location, not an inspection. Confirm anything that matters with the municipality, Conservation Halton or the record’s publisher.
Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Town of Oakville.
Lot
- Street frontage
- 57.55 ft17.5 m
- Depth
- 137.43 ft41.9 m
The record marks this lot irregular, so its area is not the frontage multiplied by the depth. It is not given here. Confirm with a survey before you buy.
Source: the MLS® listing record.
Land transfer tax on this home
- Ontario land transfer tax
- $41,450
- Total land transfer tax
- $41,450
- First-time buyer rebates (Ontario up to $4,000)
- −$4,000
- Total for first-time buyers
- $37,450
See how this is worked out
- 0.5% on the first $55,000
- $275
- 1.0% from $55,000 to $250,000
- $1,950
- 1.5% from $250,000 to $400,000
- $2,250
- 2.0% from $400,000 to $2,000,000
- $32,000
- 2.5% from $2,000,000 to $2,199,000
- $4,975
- Ontario total
- $41,450
An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.
Schools
Nearest schools
Straight-line distances. Check catchments with the board.
ElementaryEQAO average 2024–25
- River Oaks Public SchoolHalton DSBPublic · grades JK–865%Grade 6 average400 m
- Our Lady of Peace Catholic Elementary SchoolHalton CDSBCatholic · grades JK–885%Grade 6 average850 m
- Sunningdale Public SchoolHalton DSBPublic · grades 1–8 · French Immersion93%Grade 6 average1.3 km
- École élémentaire du ChêneConseil scolaire ViamondeFrench-language public · grades JK–699%Grade 6 average2.7 km
SecondaryGrade 9 math 2024–25
- Holy Trinity Catholic Secondary SchoolHalton CDSBCatholic · grades 9–1269%Grade 9 math1 km
- École secondaire Gaétan GervaisConseil scolaire ViamondeFrench-language public · grades 9–1285%Grade 9 math1.9 km
- Gary Allan High School - STEPHalton DSBPublic · grades 9–12—2 km
- White Oaks Secondary SchoolHalton DSBPublic · grades 9–1281%Grade 9 math2 km
EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.
Searches this home is in
Keep looking
The ledger
What it costs to own
Worked out for this home. Change any number.
A month, all in
$10,956
- Mortgage$10,033
- Property tax$923
A planning figure, not a quote.
Land transfer tax
$41,450
$37,450 for first-time buyers.
Rent, similar homes
$4,100
a month, median asking rent of 5 similar homes in River Oaks.
Community
Who lives around it
Similar homes
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Shemeer AhmadVALERY REAL ESTATE INC.
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