2203 Winding Woods Dr
River Oaks, Oakville, Ontario L6H 5T9
- Bedrooms
- 4
- Bathrooms
- 5
- Size
- 3,500–5,000sq ft
- Per sq ft
- $517at the range’s middle
- Lot
- 57.55 x 137.43 ft
- Tax a year
- $11,0702026 tax year
- Parking
- 62 attached
- Days on market
- Members
The brief
About 2203 Winding Woods Dr
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.
Insights
Condition Score
Good73/1001 documented update signal
Source: Listing age, structured features and disclosed update language; not an inspection.
Cashflow Quality
Shortfall5/100−$6,106/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Source: Median of 59 detached homes with 4 bedrooms for lease in Oakville right now. Cost of owning counts the mortgage and property tax.
Condition uses listing-record signals, not an inspection.
The home
Key facts
- Tax
- $11,070 / 2026
- MLS® number
- W13797086
- Board
- TRREB MLS®
- Property Type
- Detached
- Days on market
- Size
- 3500-5000 sqft
- Lot Size
- 57.55 x 137.43 ft
- Listed on
- Parking
- 2 Attached, 6 Parking
Property details
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
Additional
- Roof
- Asphalt Shingle
- Fireplace
- Yes
- Pool
- None
- Den
- Yes
- Family room
- Yes
- Extras
- See Schedule C
Rooms
| Room | Size | Features | Level |
|---|---|---|---|
| Breakfast | 3.03 × 6.68 m | — | Main |
| Kitchen | 7.89 × 3.89 m | — | Main |
| Dining | 5.89 × 3.65 m | — | Main |
| Family | 4.11 × 6.08 m | — | Main |
| Living | 3.89 × 5.47 m | — | Main |
| Primary | 6.06 × 8.93 m | — | 2nd |
| 2nd Br | 3.66 × 3.95 m | — | 2nd |
| 3rd Br | 3.98 × 5.06 m | — | 2nd |
| 4th Br | 3.94 × 4.84 m | — | 2nd |
| Den | 3.66 × 5.51 m | — | 2nd |
| Rec | 6.9 × 13.78 m | — | Bsmt |
| Office | 3.18 × 6.53 m | — | Bsmt |
| Utility | 3.94 × 7.46 m | — | Bsmt |
Listing history
Buy/sell history for 2203 Winding Woods Dr, Oakville, Ontario
Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $2,199,000 | N/A | For Sale | W13797086 |
Members see the full history. Prices are hidden from signed-out visitors.
The numbers
Mortgage Calculator
Plan with the current asking price
CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.
Mortgage Details
4.8% · 5-year term · 25-year amortization · 20% down
- Total down payment
- $439,800
- Total mortgage amount
- $1,759,200
- Total interest payment
- $1,250,700
- Total purchase cost
- $3,449,700
- Mortgage payment
- $10,033/mo
Cash Flow Analysis
If you rented this home out at 20% down
Break-even down payment
69%Monthly carrying cost
$10,956- Rent $4,850
- Shortfall $6,106
Rental income opens at $4,850, the median asking rent of 59 comparable homes for lease in Oakville. Type over it with the rent you expect. This is a planning tool, not advice.
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.
Estimate
Estimated value requires sign in
Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.
The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Kassaundra Dobson, Broker of Record for a full comparative market analysis.
Comparable sales
Comparable sales require sign in
Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.
The land
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 and environment
Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.
Water and conservation2
- No mapped wetland within 120 m120 m
- No water-supply well recorded within 250 m250 m
Province of Ontario open data
Planning and building activity2
- Outside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areasAt the address
- Nearest airport: 9.9 km9.9 km
Province of Ontario open data
Around the home2
- Transit stop within 400 mFrom the transit agency’s published stop map; the nearest is 150 m away. Routes and stops change; check the agency’s schedule.400 m
- A trail on the Ontario trail network within 1 km1 km
Municipal transit open data · Province of Ontario open data
Environmental records4
- No licensed pit or quarry within 2 km2 km
- No recorded oil, gas or salt well within 250 m250 m
- No facility within 1 km reports pollutant releases to Environment CanadaOnly facilities above the inventory’s reporting thresholds are listed.1 km
- No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km
Province of Ontario open data · Government of Canada open data
Power and internet3
- Electricity is distributed here by Oakville Hydro Electricity Distribution Inc.At the address
- Wired internet 50/10 Mbps or faster is listed at this locationFixed 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.At the address
- Across the surrounding area: fibre to the home, cable, DSL internet listedFibre 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.Area-wide
Ontario Energy Board · Innovation, Science and Economic Development Canada
Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Conservation Haltonor 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.
The market
Detached homes for sale in River Oaks right now
- For sale now
- 27
- Median asking price
- $1.7M
- New in 7 days
- 0
- Price cuts
- 26%
Middle half: $1.43M to $2.09M
11 in 28 days
7 listings
This home is asking 29% 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.
Market area · filters apply to the charts below
The street
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.
Schools nearby
| Elementary | Type | Distance | EQAO average 2024–25 |
|---|---|---|---|
| River Oaks Public SchoolHalton DSB | Public · grades JK–8 | 400 m | 65%Grade 6 average |
| Our Lady of Peace Catholic Elementary SchoolHalton CDSB | Catholic · grades JK–8 | 850 m | 85%Grade 6 average |
| Sunningdale Public SchoolHalton DSB | Public · grades 1–8 · French Immersion | 1.3 km | 93%Grade 6 average |
| École élémentaire du ChêneConseil scolaire Viamonde | French-language public · grades JK–6 | 2.7 km | 99%Grade 6 average |
| Secondary | Type | Distance | Grade 9 math 2024–25 |
|---|---|---|---|
| Holy Trinity Catholic Secondary SchoolHalton CDSB | Catholic · grades 9–12 | 1 km | 69%Grade 9 math |
| École secondaire Gaétan GervaisConseil scolaire Viamonde | French-language public · grades 9–12 | 1.9 km | 85%Grade 9 math |
| Gary Allan High School - STEPHalton DSB | Public · grades 9–12 | 2 km | — |
| White Oaks Secondary SchoolHalton DSB | Public · grades 9–12 | 2 km | 81%Grade 9 math |
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.
The verdict
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Sold prices in River Oaks are shown to signed-in members.