2203 Winding Woods Drive, Oakville, ON
River Oaks, Oakville · MLS® W13227366
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 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.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- W13227366
- Bedrooms
- 4
- Bathrooms
- 5 (2 half)
- Size
- 3500-5000
- Lot
- 57.55 × 137.43 ft
- Cross streets
- River Oaks Blvd/Winding Woods
- Parking
- 2 garage · 6 parking (attached)
- Basement
- Finished
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Brick
- Foundation
- Unknown
- Roof
- Asphalt Shingle
- Sewer
- Sewer
- Property tax
- $11,070 / 2026
- Days on market
- 46
- Listing brokerage
- RE/MAX ESCARPMENT REALTY INC.
Rooms
Listed at $2,399,000, this home is about 25% below comparable homes, worth a close look. The number above is my independent estimate of value, not the asking price.
There were not many closely comparable homes right in River Oaks, so I widened the search to the surrounding area.
Based on 7 similar homes nearby, adjusted for size, beds, and baths.Median of 7 comparable active listings, adjusted for size, beds, and baths. The city (MPAC) assessment points to about $2.41M, lower than the comparables and worth a second look. The comparable range is wide here, so treat this as a rough read until I run a full CMA.
How I got there
Here is the exact math behind the estimate. I start from the closest comparable listing and adjust for the real differences (size, beds, baths) to land on a like-for-like value for this home.
- Closest comparable, listed at $3.20M
- Bedrooms −$30K
- Bathrooms +$15K
- Adjusts to $3.18M
That comparable adjusts to $3.18M; the $3.18M estimate above is the median of all 7 comparables, which is steadier than any single home.This uses comparable active listings, not sold prices. Lot, condition, and finishes are my in-person call, and I can run a full CMA with recent solds.
On location, this is a more car-dependent spot, so buyers here typically drive. Transit is limited nearby. Worth weighing if transit access matters to you.
Total price vs nearby homes. Fair value about $3.18M, median of 7 comparables.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Ravine lot: privacy and premium value, but confirm the buildable area and any conservation limits.
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person.
- Worth verifying
- Value driver
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 3 closest active listings nearby.
See all comparable homesThis home lists 18% below the area average of $686/sqft.
40 days longer than the Oakville average (6 days).
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
River Oaks, Oakville, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
Getting around
Car-DependentA walkability read built from the amenities around this home: how close the nearest transit stop is, and how many grocery, dining, park, and pharmacy destinations fall within a 15-minute walk. It is a guide, not a guarantee. Places data from Google.
Almost all errands require a car.
Within a 15-minute (1.5 km) walk.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Oakville.
Get the full neighbourhood report (schools, parks, transit & safety) →
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 3.99% via Ratehub.ca (as of July 18, 2026); conventional rates run a little higher.
Mortgage amount $1,919,200 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $10,242
- Property tax
- $923
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $11,164
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $46,450
- Estimated closing costs
- $46,450
Plus your down payment of $479,800. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $614,494
- Principal paid down
- $244,411
- Interest paid
- $370,083
- Balance remaining
- $1,674,789
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of RE/MAX ESCARPMENT REALTY INC.. MLS®/PropTx.