2203 Winding Woods Drive

FOR SALE
$2,199,000
2203 Winding Woods Drive, Oakville
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
2203 Winding Woods Drive
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4
BEDROOMS
5
BATHROOMS
1
KITCHENS
9 + 2
ROOMS
W13797086
MLSID
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Property Description
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.
Nearby Intersections
Property Features
Electric Car Charger, Golf, Park, Rec./Commun.Centre, Wooded/Treed, Ravine, Auto Garage Door Remote, Central Vacuum, Private
Property Details
Address
2203 Winding Woods Drive
Postal Code
L6H 5T9
Property Type
Detached, Detached
Zoning
RL5
Lot Size
58' x 137'
Taxes
$11,070 (2026
Basement
Finished
Exterior
Lawn Sprinkler System, Landscape Lighting, Backs On Green Belt
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
4
Garage Type
Attached
Listing contracted with Re/Max Escarpment Realty Inc.
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BEDS
4
BATHS
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4
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4
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$1,999,990
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$1,979,000
FOR SALE
Welcome to this beautifully maintained Fernbrook home in the highly sought-after Joshua Creek community, offering nearly 3,000 sq. ft. of above-grade living space and a spacious, functional layout thoughtfully designed for comfortable family living. The main floor features 9-foot ceilings, hardwood flooring, and a soaring open-to-above living room that creates an impressive sense of space and fills the home with natural light. A gas fireplace adds warmth to the inviting living space, while the eat-in kitchen features granite countertops, ample cabinetry, and plenty of room for everyday family gatherings. Upstairs, four generously sized bedrooms provide comfortable accommodations for the entire family, including a spacious primary retreat with a large ensuite. Quartz countertops add an updated touch to the bathrooms.Outside, the professionally landscaped property extends the living space with interlocking stone, a deck and flagstone front porch - ideal for relaxing and entertaining. The finished basement with an additional bathroom offers flexible space for a recreation room, home office, gym, or guest area.Recent updates include attic insulation (2021), dishwasher, washer and dryer (2021), air conditioning (2023), stove (2025), and refrigerator (2026). Ideally located within walking distance to Iroquois Ridge High School, Iroquois Ridge Community Centre and Library, and close to parks, trails, shopping, major highways, and everyday amenities. A wonderful opportunity to own a well-cared-for family home in one of Oakville's most established and desirable neighbourhoods.
75 Carnegie Drive, Oakville
4
BEDS
4
BATHS
$1,950,000
FOR SALE
Fernbrook Executive Collection Stoney Creek Model featuring a grand double-door entry leading to an impressive foyer with double closets. This home offers a spacious double car garage with exceptional 11-ft ceilings-ideal for car enthusiasts with potential for a car lift. Enjoy soaring 10-ft ceilings on the main floor, 9-ft ceilings on the second floor and in the basement, creating a bright and airy living space throughout.This extensively upgraded home showcases hardwood flooring, an upgraded staircase, elegant mouldings, pot lights, and an extended kitchen with additional cabinetry and a spacious pantry. The thoughtfully designed open-concept layout is perfect for both entertaining and everyday living, while the inviting family room with a cozy fireplace provides the perfect space to relax and unwind. Ideally located close to shopping plazas, restaurants, banks, supermarkets, and a wide range of everyday amenities, offering exceptional convenience for modern family living.
1302 Hillview Crescent, Oakville
4
BEDS
4
BATHS
$1,950,000
FOR SALE
Welcome To One of Falgarwood's Most Exceptional Properties, Perfectly Positioned on a Premium 75' X 150' Ravine Lot Backing Directly onto Morrison Valley South. This Fully Renovated Four-Bedroom Executive Home Offers a Rare Blend of Luxury, Privacy, & Everyday Comfort. Surrounded by Mature Trees and Spectacular Ravine Views, Retreat to Your Own Backyard Oasis Where Nature Becomes Part of Your Everyday Lifestyle. The Beautifully Renovated Interior Showcases Rich Hardwood Flooring, Spacious Principal Rooms, and a Stunning Chef-Inspired Kitchen with Quartz Countertops, Stainless Steel Appliances, and a Large Centre Island. The Inviting Family Room with a Gas Fireplace Overlooks the Breathtaking Ravine. While the Upper-Level Features Four Generous Bedrooms, including a Luxurious Primary Retreat with a Spa-Inspired Ensuite, Walk-In Closet, Vaulted Ceiling, & Gas Fireplace. The Professionally Finished Walk-Out Basement Adds Exceptional Living Space with a Theatre Room, Gym, And Direct Access to Your Private Outdoor Retreat. Unwind in the Heated Inground Pool with Waterfall, relax in the Hot Tub, Entertain on The Expansive Patios, or Simply Enjoy the Peace & Tranquility of One of Falgarwood's Most Coveted Ravine Settings. Minutes to Top-Rated Schools, Parks, Trails, Sheridan College, GO Transit, Shopping, & Major Highways. A Truly Rare Opportunity in One of Oakville's Most Desirable Neighbourhoods.
1075 Mayfair Road, Oakville
4
BEDS
4
BATHS
$1,949,900
FOR SALE
Luxury living in prestigious Glen Abbey. This exceptional custom-renovated executive residence showcases sophisticated design, elevated finishes, and an uncompromising attention to detail. From the moment you enter, the quality and craftsmanship are unmistakable.The open-concept main floor features 45-degree diagonal hardwood flooring, elegant wainscoting, and a beautiful living room with a quartz-framed gas fireplace designed for effortless entertaining. The showstopping chef's kitchen offers a massive full-slab island, premium KitchenAid appliances, extensive storage, and a dedicated beverage station with seamless flow into the formal dining room. Expansive windows and glass doors fill the home with natural light and open to a private, resort-style backyard oasis complete with a motorized hardtop hot tub and a powered custom outbuilding-perfect for entertaining, relaxing, and enjoying the outdoors year-round.Upstairs, four generous bedrooms are complemented by a versatile bonus den and solid wood core doors throughout. The luxurious primary suite is a private retreat with extensive custom built-in cabinetry and a spa-inspired ensuite featuring radiant heated floors, marble countertops, premium Kohler fixtures, an oversized walk-in shower, and a Toto bidet toilet.The fully finished lower level adds exceptional living and entertaining space with dramatic high ceilings, plush Berber carpet, custom millwork, and a second gas fireplace. A stylish wet bar, media area, full three-piece bathroom, and dedicated workshop offer incredible flexibility for family living, guests, hobbies, and entertainment. Extensive upgrades include custom roller window coverings, updated windows, 200-amp electrical service, updated roof, new eavestroughs and downspouts, plus a furnace and heat pump replaced just three years ago to save you money on utilitles. Simply move in and experience the perfect blend of elegance, comfort, quality, and resort-style living.
144 North Park Boulevard, Oakville
4
BEDS
4
BATHS
$1,949,000
FOR SALE
Beautifully maintained detached home on a 45-ft lot in Oakville's sought-after Glenorchy community, featuring 4 spacious bedrooms, 3 second-floor bathrooms, and a rare 3-car tandem garage. Elegant finishes include 10-ft ceilings on the main floor, 9-ft ceilings upstairs, smooth ceilings, crown moulding, upgraded 8-ft doors, and a dark-stained oak staircase with iron pickets. The spacious main level offers separate living, dining, and family rooms, providing an inviting setting for everyday living and entertaining. The chef's kitchen features premium cabinetry, built-in high-end appliances, a backsplash, expansive granite countertops, and a Kinetico home water system. The dining room opens to a beautifully landscaped English-style garden with an interlocking patio, while the family room features a contemporary gas fireplace. Upstairs, a versatile loft and upgraded laundry room complement the well-designed layout. The generous primary suite offers a coffered ceiling, a 5-piece ensuite, and a large walk-in closet with custom organizers. A second bedroom features its own 4-piece ensuite, while the third and fourth bedrooms share a convenient Jack-and-Jill bathroom, offering an ideal layout for family living. Upgraded closet organizers provide practical storage throughout. Large windows fill the home with natural light, complemented by California shutters and quality drapery. The tandem garage provides additional space for a boat or storage. Within walking distance of parks, trails, playgrounds, and schools, this move-in-ready home combines spacious family living with beautifully finished indoor and outdoor spaces.
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