The Jennifer Jones Team, LPT Realty, Brokerage

Oakville, ON

2203 Winding Woods Drive

$2,199,000

Data last updated Nov 3, 2026, 9:50 p.m. ET. By using this site you agree to our Terms of Use.

Detached at 2203 Winding Woods Drive, Oakville, ON
2203 Winding Woods Drive, Oakville, ON, photo 22203 Winding Woods Drive, Oakville, ON, photo 3

Property facts

Price
$2,199,000
Type
Detached
Bedrooms
4
Bathrooms
5
MLS®
W13797086
Status
active
Brokerage
RE/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.

Location

Search the full MLS®

More details

Property tax
$11,070 (2026)
Days on market
49
Style
2-Storey
Lot
57.55 × 137.43 Feet
Parking
6 spaces · 2 garage · Attached
Basement
Finished
Heating
Forced Air
Air conditioning
Central Air
Neighbourhood
River Oaks
Major intersection
River Oaks Blvd/Winding Woods

Rooms

RoomLevelSize (m)Features
Utility RoomBasement7.46 × 3.94—
OfficeBasement6.53 × 3.18—
RecreationBasement13.78 × 6.9—
Primary BedroomSecond8.93 × 6.06—
Family RoomMain6.08 × 4.11—
DenSecond5.51 × 3.66—
BreakfastMain6.68 × 3.03—
Bedroom 4Second4.84 × 3.94—
Dining RoomMain3.65 × 5.89—
Living RoomMain5.47 × 3.89—
Bedroom 2Second3.95 × 3.66—
KitchenMain3.89 × 7.89—
Bedroom 3Second5.06 × 3.98—

Details from PropTx (TRREB MLS®) via Repliers. Information deemed reliable but not guaranteed.

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