Detached House for sale at 2203 Winding Woods Drive, Oakville, Ontario, L6H 5T9 - River Oaks - MLS: W13064222

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2203 Winding Woods Drive

Oakville, Ontario, L6H 5T9 - River Oaks

$2,549,000

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Neighbourhood

River Oaks
Major Intersection

River Oaks Blvd/Winding Woods

Listed Since: 18 day(s)
Last update: 5 day(s) ago

Virtual Tour

Overview

Property Type

Detached, 2-Storey
Bedrooms

4
Bathrooms

5
Basement

Finished
Kitchen

1
Total Parking

6 (2 Attached Garage)
Lot Size

57.55x137.43 (Feet)
Taxes

$10,858.00 (2025)
Type

Freehold

Property Description

Property description for 2203 Winding Woods Drive, Oakville

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 ft 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.

Listed by RE/MAX ESCARPMENT REALTY INC.

Property details

MLS #

W13064222
Sq. Ft

3500-5000
Sq. Ft. Source

MLS
Lot Irregularities

Y
Year Built

Available Upon Request
Pool

None
Drive

n/a
Garage

Attached, 2 spaces
Total Parking

6
Family Room

Y
Den

Y
Exterior

Brick
Fireplace

Y
Roof

Asphalt Shingle
Foundation

Unknown
Elevator

n/a
Water View

n/a
Laundry Level

Main
Heat

Forced Air
A/C

Central Air
Water

Municipal
Water Supply

n/a
Sewers

Sewers
Central Vac

Y

MLS #

W13064222
Sq. Ft

3500-5000
Sq. Ft. Source

MLS
Lot Irregularities

Y
Year Built

Available Upon Request
Pool

None
Drive

n/a
Garage

Attached, 2 spaces
Total Parking

6
Family Room

Y
Den

Y
Exterior

Brick
Fireplace

Y
Roof

Asphalt Shingle
Foundation

Unknown
Elevator

n/a
Water View

n/a
Laundry Level

Main
Heat

Forced Air
A/C

Central Air
Water

Municipal
Water Supply

n/a
Sewers

Sewers
Central Vac

Y

Breakfast

6.68 x 3.03 ft Main level
Kitchen

3.89 x 7.89 ft Main level
Dining

3.65 x 5.89 ft Main level
Family

6.08 x 4.11 ft Main level
Living

5.47 x 3.89 ft Main level
Primary

8.93 x 6.06 ft 2nd level
2nd Br

3.95 x 3.66 ft 2nd level
3rd Br

5.06 x 3.98 ft 2nd level
4th Br

4.84 x 3.94 ft 2nd level
Den

5.51 x 3.66 ft 2nd level
Rec

13.78 x 6.9 ft Bsmt level
Office

6.53 x 3.18 ft Bsmt level
Utility

7.46 x 3.94 ft Bsmt level

Contact Manoj Kukreja

Sales Representative,
Century 21 People’s Choice Realty Inc.,
Brokerage
(647) 576 - 2100

Local Real Estate Price Trends for Detached in River Oaks

Active listings

Average Selling Price of a Detached

April 2026

$1,666,993

Last 3 Months

$1,523,206

Last 12 Months

$1,522,279

April 2025

$1,572,273

Last 3 Months LY

$1,559,369

Last 12 Months LY

$1,652,260

Change

-2%

Change

-8%

Historical Average Selling Price of a Detached in River Oaks

Average Selling Price

3 years ago

$1,826,489

Average Selling Price

5 years ago

$1,517,633

Average Selling Price

10 years ago

$953,606

Change

-9%

Change

10%

Change

75%

Number of Detached Sold

April 2026

Last 3 Months

Last 12 Months

April 2025

Last 3 Months LY

Last 12 Months LY

Change

27%

Change

83%

Change

13%

How many days Detached takes to sell (DOM)

April 2026

Last 3 Months

Last 12 Months

April 2025

Last 3 Months LY

Last 12 Months LY

Change

47%

Change

Average Selling price

Inventory Graph

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First time home buyer

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Down Payment(%)*

Additional information

Provincial Land Transfer Tax

Ontario Land Transfer Tax Rebate

Toronto Land Transfer Tax

Toronto Land Transfer Tax Rebate

PST on CMHC Insurance Premium

Lawyer Fees

$2,825

Government Registration Fee's

$164

Title Insurance

Closing Cost Total

Total Cash flow for purchasing this property

Provincial Land Transfer Tax

Ontario Land Transfer Tax Rebate

Toronto Land Transfer Tax

Toronto Land Transfer Tax Rebate

PST on CMHC Insurance Premium

Lawyer Fees

$2,825

Government Registarion Fee's

$164

Title Insurance

Purchase Price

Down Payment($)

Down Payment(%)*

First time home buyer

* A down payment of less than 20% is permitted only for first-time home buyers purchasing their principal residence. The minimum down payment required is 5% for the portion of the purchase price up to $500,000, and 10% for the portion between $500,000 and $1,500,000. For properties priced over $1,500,000, a minimum down payment of 20% is required.