Gallery
50
$2,199,000

CindySEZ

$2,064,828

CindySEZ

$2,064,828

2203 Winding Woods Drive, Oakville
River Oaks
4 Beds
5 Baths

MLS#W13797086

2203 Winding Woods Drive, Oakville

$2,199,000

River Oaks
4 Beds
5 Baths

MLS#W13797086

CindySEZ

$2,064,828

CindySEZ

$2,064,828

Home DetailsFeaturesExterior FeatureRoomsSales History

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.

Home Details

Home Details

  • Category

  • Residential

  • Status

  • New

  • Days on Market

  • 35 Days

  • List date

  • 09/17/2026

  • Listing Updated On

  • 10/15/2026

  • Taxes / Year

  • $11,070 / 2026

  • Style

  • Detached

  • Type

  • 2-Storey

  • Lot Size

  • 0.18 Acres

Features

Features

Beds & Baths

  • Total Beds

  • 4

  • Baths

  • 5

Heating & Cooling

  • Heating Type

  • Forced Air

  • Air Conditioning

  • Central Air

  • Number of Fireplaces

  • 2

Parking & Garage

  • Total Parking

  • 8

  • Number of Garage Spaces

  • 2

Basement

  • Desc

  • Finished

Appliances & Equipment

Appliances & Equipment

Exclusions

See Schedule C
Neighbourhood Influences

Neighbourhood Influences

Electric Car Charger
Golf
Park
Rec./Commun.Centre
Wooded/Treed
Ravine
Exterior Feature

Exterior Feature

Lot

  • Acres

  • 0.18 Acres

  • Frontage

  • 57 Ft

  • Depth

  • 137 Ft

  • Irregular shape

  • Y

Construction Details

  • Foundation Type

  • Unknown

  • Roof Material

  • Asphalt Shingle

  • Exterior

  • Brick

Water & Sewer

  • Sewer

  • Sewer

Legal

  • Brokerage

  • Re/Max Escarpment Realty Inc.

  • Legal Description

  • Pcl40-1, Sec 20m531; Lt 40, Plan M531, Oakville

Rooms

Rooms

Lower Floor

  • Utility Room

  • 3.94 / 7.46

  • Office

  • 3.18 / 6.53

  • Recreation

  • 6.9 / 13.78

Second

  • Primary Bedroom

  • 6.06 / 8.93

  • Den

  • 3.66 / 5.51

  • Bedroom 4

  • 3.94 / 4.84

  • Bedroom 2

  • 3.66 / 3.95

  • Bedroom 3

  • 3.98 / 5.06

Main Floor

  • Family Room

  • 4.11 / 6.08

  • Breakfast

  • 3.03 / 6.68

  • Dining Room

  • 5.89 / 3.65

  • Living Room

  • 3.89 / 5.47

  • Kitchen

  • 7.89 / 3.89

Sales History

Sales History

Active

(35 days on market)

Viewing now

New

2026-09-17

Listed For Sale

$2,199,000

MLS# W13797086

1900-06-21

0

View

1900-06-21

1900-06-21

Listed For Sale

$0

MLS# W13227366

1900-06-21

0

View

1900-06-21

1900-06-21

Listed For Sale

$0

MLS# W13064222

2203 Winding Woods Drive
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