2203 Winding Woods Drive, Oakville, ON L6H 5T9
1015 - RO River Oaks, Oakville · Near River Oaks Blvd/Winding Woods · View map
About this home
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.
The home
- Type
- 2-storey detached home
- Style
- 2-Storey
- Square footage
- 3500-5000 sq ft
- Bedrooms
- 4
- Bathrooms
- 5
- Kitchens
- 1
- Rooms
- 9
- Basement
- Finished
- Lot size
- 57.6 x 137.4 ft
- Faces
- East
- View
- Trees/Woods
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Brick
Heating & cooling
- Heating fuel
- Gas
- Heating type
- Forced Air
- Air conditioning
- Central Air
- Fireplace
- Yes
- Central vacuum
- Yes
Garage & parking
- Garage
- Attached
- Garage spaces
- 2
- Driveway spaces
- 4
- Total parking
- 6
- Parking features
- Private
Taxes & other
- Property taxes
- $11,070/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- Flexible
- Cross street
- River Oaks Blvd/Winding Woods
- Neighbourhood
- 1015 - RO River Oaks
More
- Price per sq ft
- ~$517 (at 4,250 sq ft)
- MLS® number
- W13797086
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The home and its surroundings
- Auto Garage Door Remote
- Central Vacuum
- Electric Car Charger
- Golf
- Park
- Rec./Commun.Centre
- Wooded/Treed
- Ravine
- Lawn Sprinkler System
- Landscape Lighting
- Backs On Green Belt
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
2203 Winding Woods Drive, Oakville, ON L6H 5T9
1015 - RO River Oaks, Oakville · Near River Oaks Blvd/Winding Woods
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Listing history for 2203 Winding Woods Drive
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 2203 Winding Woods Drive
Answers come straight from this home’s MLS® listing.
How much is 2203 Winding Woods Drive listed for, and what would it cost each month?
2203 Winding Woods Drive is listed for $2,199,000. With 20% down ($439,800), the mortgage payment would be roughly $8,870 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $9,793 a month, all in. That figure is an illustration, not a quote.
Is 2203 Winding Woods Drive freehold or a condo, and is there a monthly fee?
2203 Winding Woods Drive is a 2-storey detached home in 1015 - RO River Oaks, Oakville. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 2203 Winding Woods Drive have?
2203 Winding Woods Drive has 4 bedrooms and 5 bathrooms.
Does 2203 Winding Woods Drive have a garage and parking?
Yes. The listing shows the garage as attached, with room for 2 cars. The driveway adds 4 spaces. In total the listing counts 6 parking spaces.
Does 2203 Winding Woods Drive have a finished basement?
The listing describes the basement as finished. Finished basement space is usually not counted in the square footage shown.
What style of home is 2203 Winding Woods Drive?
2203 Winding Woods Drive is a 2-storey detached home. A 2-storey detached house has its living space on the main floor and the bedrooms upstairs, on its own lot with no shared walls.
How big is 2203 Winding Woods Drive, and what is the lot size?
The listing puts the home between 3,500 and 5,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 57.6 x 137.4 ft.
How is 2203 Winding Woods Drive heated and cooled?
Heating is forced air (gas). Cooling is central air.
What are the property taxes for 2203 Winding Woods Drive?
Property taxes are $11,070 a year (2026), or about $923 a month.
Where is 2203 Winding Woods Drive?
2203 Winding Woods Drive is in the 1015 - RO River Oaks community of Oakville. The nearest main intersection is River Oaks Blvd/Winding Woods. The postal code is L6H 5T9.
Is 2203 Winding Woods Drive still for sale?
Yes. It is an active listing (MLS® W13797086). Listings here update from the board through the day and come down once a home sells.
What are similar detached homes near 2203 Winding Woods Drive asking?
Similar detached homes for sale nearby right now include 340 Oakridge Court at $2,088,000 (4 bed), 435 March Crescent at $1,899,000 (4 bed) and 2087 Mayflower Boulevard at $1,799,900 (4+2 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 2203 Winding Woods Drive sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 2203 Winding Woods Drive?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar detached homes nearby
More detached homes for sale near 1015 - RO River Oaks, picked by style, size and price.
2-storey detached home$2,088,000340 Oakridge Court, Oakville4 bed · 4 bath · 1015 - RO River OaksCourtesy of: ROYAL LEPAGE REAL ESTATE SERVICES LTD.View home →
2-storey detached home$1,899,000435 March Crescent, Oakville4 bed · 5 bath · 1015 - RO River OaksCourtesy of: RE/MAX ABOUTOWNE REALTY CORP.View home →
2-storey detached home$1,799,9002087 Mayflower Boulevard, Oakville4+2 bed · 4 bath · 1015 - RO River OaksCourtesy of: SAM MCDADI REAL ESTATE INC.View home →Courtesy of: RE/MAX ESCARPMENT REALTY INC.
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.