2203 Winding Woods Drive
1015 - RO River Oaks, Oakville, L6H 5T9
FOR SALE
$2,399,000

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Property Description
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.
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Nearby Intersections
Property Features
Electric Car Charger, Hospital, Park, Golf, Rec./Commun.Centre, Wooded/Treed, Auto Garage Door Remote, Central Vacuum
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Property Details
Address
2203 Winding Woods Drive
Community
City
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
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
4
Garage Type
Attached
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Listing contracted with Re/Max Escarpment Realty Inc.
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Welcome to Glen Abbey Encore! A neighborhood that offers the best variety of amenities in Canada's best place to live. There's great shopping, top rated public, separate and private schools, popular restaurants, Rec Centers, Libraries & more all close at hand. Golfers will love the proximity to Deerfield Golf Club, Glen Abbey Golf Course and many others nearby. This stunning Modern 4 bedroom + 5 bathroom residence blends refined design with everyday functionality in a vibrant, family-friendly neighbourhood. Impressive 10 ft ceilings on the main floor and 9 ft ceilings on the second level and finished lower level. Enjoy cozy nights with a double sided fireplace in the Dining and Family room. Enjoy Chef inspired meals prepared in your Gourmet Kitchen with BI Cooktop and Oven. The Primary Bedroom features a large walk in closet and elegant spa ensuite with free standing tub. Spacious bedrooms one with ensuite and 2 sharing a Jack and Jill bathroom. The beautiful parks, beaches and marinas of Lake Ontario are just minutes south, & commuters will enjoy proximity to Bronte GO Station and Hwy 407 and the QEW/403. With all this and more right at your doorstep, this is one Encore that undoubtedly deserves a standing ovation.
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This is your opportunity to acquire an exceptionally rare location on a prestigious private cul de-sac street in Oakville. This charming house has views of the lake only seconds away. To live south of Lakeshore near waters edge is a dream come true. This exquisite raised bungalow home has a premium sized fenced lot with frontage of 60ft by 144ft boasting 8,837 ft sq. Open concept main level with hardwood flooring and gorgeous natural light. The kitchen has high end appliances with a Bosch dishwasher, Thor double oven stove, and Thor wine fridge. Your hot tub under the beautiful mature trees feels like your vacation away up north in Muskoka. This is truly a once in a lifetime opportunity to get in on this private beautiful street. You don't want to miss out!
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Exquisite Luxury Home on a Ravine Lot in Prestigious Seven Oaks! Boasting over 5,400 sq. ft. of opulent living space, including 3,600+ sq. ft. above grade, this masterpiece is designed for those who appreciate fine craftsmanship and unparalleled detail.Step into grandeur with soaring 11' ceilings on the main floor and solid 9' wood doors throughout. Crystal chandeliers illuminate the elegant living and dining areas, creating an entertainer's dream with custom wainscoting and detailed ceiling designs.The chef's kitchen is a showstopper, featuring built-in Sub-Zero & Wolf appliances, Italian quartz countertops, and dual-tone extended cabinetry. The family room exudes warmth, showcasing a waffle ceiling, gas fireplace with stone mantle, and oversized windows that flood the space with natural light. A grand staircase with glass railings adds to the home's sophisticated charm.The primary suite is a retreat with double walk-in closets leading to a spa-inspired ensuite with upgraded marble countertops. The second bedroom boasts a wall of windows, walk-in closet, and a private 3-piece ensuite, while the third bedroom rivals the primary in size, featuring a deep walk-in closet and Jack & Jill ensuite with 9'ceilings.A professionally finished basement with soaring 10' ceilings offers a soundproofed theatre room, linear gas fireplace, and custom shelving. A roughed-in sauna/steam room and second kitchen add future potential, complete with gas range, cabinetry lighting, and appliance rough-ins.Backing onto lush green space, this home is perfectly situated near top-rated schools, parks, shopping, dining, community centers, and major highways.This is the new definition of luxury!
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Spectacular 1/2 acre property nestled on a quiet court in highly sought-after Southeast Oakville. This impressive pie-shaped lot spans 0.544 acres (23,691 sq ft) and offers exceptional privacy, mature trees and an in-ground pool. Zoned RL1-0. Located in the prestigious Morrison neighbourhood, this property presents an outstanding opportunity to renovate or build your dream home. Just a 5-minute walk to top-ranked schools, including Oakville Trafalgar High School and Maple Grove Public School. Ideally situated near Lake Ontario, scenic Gairloch Gardens and the shops and restaurants of Downtown Oakville. Property is being sold "As Is, Where Is".
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