2203 Winding Woods Drive

1015 - RO River Oaks, Oakville, Ontario L6H 5T9

Overview

At a glance

Days on market39 days
ListedSep 17, 2026
UpdatedOct 15, 2026
Size3500-5000 sq ft
Lot57.55 x 137.43 Feet
Property taxes$11,070 (2026)
Parking6 spaces
BasementFinished
MLS® numberW13797086
Data sourcePropTx MLS® System
Listing brokerageRE/MAX ESCARPMENT REALTY INC.

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.

Details

Property

Style
2-Storey
Fronting on
East
Cross street
River Oaks Blvd/Winding Woods
Community
1015 - RO River Oaks
Municipality
Oakville

Inside

Bedrooms above grade
4
Bathrooms
5
Kitchens
1
Basement
Finished
Family room
Yes
Fireplace
Yes
Interior features
Auto Garage Door Remote, Central Vacuum

Utilities

Heating
Forced Air
Heating fuel
Gas
Cooling
Central Air
Sewer
Sewer

Building

Construction
Brick
Foundation
Unknown
Roof
Asphalt Shingle
Exterior features
Lawn Sprinkler System, Landscape Lighting, Backs On Green Belt
Pool
None

Parking

Garage
Attached
Parking spaces
4
Total parking
6
Driveway
Private

Land

Frontage
57.55
Depth
137.43
Lot size units
Feet
Lot irregularities
69.01 x 137.43 x 57.55 x 154.95
Waterfront
No
Topography
Wooded/Treed
Property features
Electric Car Charger, Golf, Park, Rec./Commun.Centre, Wooded/Treed, Ravine
Rooms (13)
RoomLevelSizeFeatures
BreakfastMain6.68 x 3.03
KitchenMain3.89 x 7.89
Dining RoomMain3.65 x 5.89
Family RoomMain6.08 x 4.11
Living RoomMain5.47 x 3.89
Primary BedroomSecond8.93 x 6.06
Bedroom 2Second3.95 x 3.66
Bedroom 3Second5.06 x 3.98
Bedroom 4Second4.84 x 3.94
DenSecond5.51 x 3.66
RecreationBasement13.78 x 6.9
OfficeBasement6.53 x 3.18
Utility RoomBasement7.46 x 3.94
Value

What it’s worth

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History

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How it compares

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Neighbourhood

Around 1015 - RO River Oaks

What’s nearby

Backs onto woodsBacks onto waterQuiet streetBackyard faces north

  • Elementary schoolRiver Oaks Public Schoolabout 6 min walk
  • High schoolHoly Trinity Catholic Secondary Schoolabout 15 min walk
  • Park about 3 min walk
  • Playground about 7 min walk
  • TrailCrosstown Heritage Trailabout 3 min walk
  • River or lakeShannon's Creekabout 1 min walk
  • Grocery storeFood Basicsabout 18 min walk
  • DowntownOakvilleabout 5.1 km
  • LibraryOakville Public Library - Sixteen Mile Branchabout 27 min walk
  • Rec centre or arenaRiver Oaks Community Centreabout 13 min walk
  • Golf courseGlen Abbeyabout 20 min walk
  • HospitalOakville Trafalgar Memorial Hospitalabout 3.4 km
  • Highway on-rampExit 117about 2.8 km
  • GO or train stationOakvilleabout 3.7 km

Approximate: straight-line distances, and the backyard and street worked out from the map pin and map data © OpenStreetMap contributors. Check school boundaries with the school board.

On the map

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Community

The 1015 - RO River Oaks market

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Costs

What it would cost

%
%
An example rate. Use the one your lender quotes.
Every monthEstimate
Mortgage payment$0
Property tax$0
Monthly total$0
At closing
Ontario land transfer tax$0

Estimates only, not financial advice. Uses Canadian semi-annual compounding, the minimum down payment and mortgage insurance rules, and Ontario’s land transfer tax brackets. Your lender and lawyer confirm the real numbers. Legal fees, title insurance and moving costs aren’t included.

Listing courtesy of RE/MAX ESCARPMENT REALTY INC.. Listing information from the PropTx MLS® System. Each listing shows the brokerage that represents it. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. Information is deemed reliable but is not guaranteed accurate by PropTx. Last updated October 26, 2026 at 8:50 p.m.

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