For Sale: 2203 Winding Woods Drive, Oakville, ON - REW
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$2,399,000
4 bd • 5 ba • 3500 - 4999 sf • House
2203 Winding Woods Drive
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$2,399,000
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2203 Winding Woods DriveOakville, ON, L6H 5T9

River Oaks
  • 4 Bed
  • 5 Bath
  • 3500 - 4999 Sqft
  • House

About this home

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' 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. (id:63626)
Listed by: Melissa Cescon, Broker, RE/MAX ESCARPMENT REALTY INC.

Home facts and features

Price details
List Price
$2,399,000
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Gross Taxes for 2026
$11,070
Home facts
Bedrooms
4
Full Bathrooms
3
Partial Bathrooms
2
Parking Spaces
6
Parking Details
Garage, Attached Garage
Property Type
House
Depth
137.4 feet
Frontage
57.7 feet
Title
Freehold
Exterior Finish
Brick
Heating Type
Forced air, Natural gas, Wood
Cooling
Central air conditioning
Basement Details
Finished,
Features
Irregular lot size, Wooded area
Appliances
Central Vacuum, Garage door opener remote(s)
Community
Agent details
Primary Agent
Primary Broker
RE/MAX ESCARPMENT REALTY INC.
Listing details
Days on REW
8 Days
MLS® Number
W13227366
Source
Canadian Real Estate Association
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Property Insights

River Oaks Public School
  • Public
  • JK - 8
Rotherglen School - Oakville Elementary
  • Private
  • PS - 8
Our Lady of Peace School
  • Catholic
  • JK - 8
St Johns School
  • Catholic
  • JK - 8
Holy Trinity Catholic Secondary School
  • Catholic
  • 9 - 12
Sunningdale Public School
  • Public
  • 1 - 8
Munn's Public School
  • Public
  • 1 - 8
St Andrew Catholic School
  • Catholic
  • JK - 8
Mother Teresa Catholic Elementary School
  • Catholic
  • JK - 8
Oodenawi Public School
  • Public
  • JK - 8
School catchments and distances are intended to be used as reference only. To verify enrolment eligibility for a property, contact the school directly.Report Incorrect Info
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Call Agent
Broker
Melissa Cescon
Phone:
(905) 845-4267
Cell:
(416) 436-9294
Office:
905-842-7677
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