view of front of property featuring an attached garage, concrete driveway, a chimney, and brick siding Features: driveway, satellite dish, gutters, brick siding, stoop, basement garage, chimney, built in garage, downspout

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back of property with a chimney, a garage, driveway, brick siding, and a lawn Features: driveway, built in garage, stoop, gutters, downspout, basement garage, chimney, lawn, fence, brick siding

entrance foyer with a chandelier, light tile patterned floors, and a high textured ceiling Features: baseboards wall, stairs, textured ceiling, recessed lighting, natural light, notable chandelier, drywall, tile floor, high ceiling

foyer entrance featuring tile patterned floors, hanging lights, and a high textured ceiling Features: drywall, textured ceiling, notable chandelier, tile floor, recessed lighting, natural light, baseboards wall, high ceiling, stairs

living area with a textured ceiling, crown molding, and hardwood / wood-style floors Features: baseboards wall, textured ceiling, crown molding, drywall, wood finish floor, natural light

kitchen featuring backsplash, glass fronted cabinets, a large island, modern cabinets, and wood finish cabinetry Features: natural light, sink, recessed lighting, backsplash, tile floor, stainless steel countertops, stovetop, white cabinets, kitchen island, drywall, medium brown cabinets, stone countertops, pendant lighting, kitchen bar, glass insert cabinets, flat panel cabinets, range hood

kitchen featuring stainless steel oven, black microwave, light tile patterned floors, backsplash, and white cabinets Features: glass insert cabinets, backsplash, flat panel cabinets, white cabinets, oven, recessed lighting, medium brown cabinets, stone countertops, tile floor, natural light, microwave

kitchen with modern cabinets, backsplash, wood finish cabinetry, light tile patterned floors, and recessed lighting Features: wine cooler, flat panel cabinets, baseboards wall, tile floor, drywall, natural light, glass insert cabinets, medium brown cabinets, stone countertops, backsplash, sink, recessed lighting

kitchen with glass insert cabinets and wood finish cabinets Features: white cabinets, natural light, glass insert cabinets, medium brown cabinets, sink, stone countertops

kitchen with stainless steel counters, tasteful backsplash, and healthy amount of natural light Features: natural light, stainless steel countertops, flat panel cabinets, sink, backsplash, dark brown cabinets, white cabinets

kitchen with stainless steel countertops, exhaust hood, backsplash, recessed lighting, and modern cabinets Features: flat panel cabinets, range hood, natural light, baseboards wall, medium brown cabinets, sink, recessed lighting, tile floor, stovetop, stainless steel countertops, white cabinets, drywall, backsplash

dual tone kitchen featuring two tone cabinets, a breakfast bar, modern cabinets, light tile patterned flooring, and a center island with sink Features: kitchen island, drywall, medium brown cabinets, range hood, white cabinets, pendant lighting, sink, baseboards wall, oven, microwave, notable chandelier, range oven, kitchen bar, stone countertops, tile floor, flat panel cabinets, recessed lighting

kitchen with island range hood, two tone color scheme, a breakfast bar area, light tile patterned flooring, and modern cabinets Features: vent, wine cooler, range hood, tile floor, flat panel cabinets, glass insert cabinets, baseboards wall, notable chandelier, medium brown cabinets, drywall, white cabinets, stovetop, recessed lighting, stone countertops, pendant lighting, oven, backsplash, kitchen island, natural light, kitchen bar, sink, microwave, l shaped kitchen

detailed view of island exhaust hood Features: drywall, range hood

kitchen with exhaust hood, dark countertops, black electric stovetop, glass fronted cabinets, and recessed lighting Features: recessed lighting, stovetop, drywall, flat panel cabinets, backsplash, countertops, glass insert cabinets, range hood, tile floor, natural light, baseboards wall, sink, medium brown cabinets

kitchen featuring extractor fan, decorative backsplash, stainless steel oven, modern cabinets, and black electric cooktop Features: backsplash, range hood, sink, recessed lighting, oven, white cabinets, flat panel cabinets, drywall, natural light, tile floor, countertops, stovetop, medium brown cabinets, microwave

kitchen with stainless steel oven, built in microwave, and modern cabinets Features: stone countertops, cream cabinets, refrigerator, medium brown cabinets, oven, flat panel cabinets, microwave

dining room featuring plenty of natural light and light tile patterned floors Features: tile floor, stovetop, sink, natural light, wine cooler, drywall

dining room with french doors, a skylight, lofted ceiling, and tile patterned floors Features: baseboards wall, high ceiling, skylight, tile floor, french doors, drywall, natural light, vent, vaulted ceiling

detailed view of a skylight Features: drywall, skylight

sunroom / solarium with vaulted ceiling, a skylight, french doors, and plenty of natural light Features: natural light, french doors, skylight

dining room with a textured ceiling, ornamental molding, suspended lighting, and dark wood-type flooring Features: notable chandelier, baseboards wall, natural light, wood finish floor, textured ceiling, vent, drywall, crown molding

dining space with healthy amount of natural light Features: natural light, drywall

dining space with french doors, dark wood-style flooring, ornamental molding, and hanging lights Features: french doors, wood finish floor, notable chandelier, drywall, vent, stairs, crown molding, textured ceiling, baseboards wall

living area featuring dark wood-style flooring, a glass covered fireplace, and a textured ceiling Features: wood finish floor, baseboards wall, drywall, natural light, tv, textured ceiling, fireplace

detailed view of vanity Features: vanity, mirror, sink

hall featuring dark carpet and an upstairs landing Features: vent, carpet, drywall, upstairs landing, notable chandelier, smoke carbon monoxide detector, textured ceiling, baseboards wall

staircase featuring tile patterned floors and a high ceiling Features: high ceiling, carpet, drywall, baseboards wall, tile floor

staircase with hanging lights and a high ceiling Features: drywall, notable chandelier, natural light, recessed lighting, high ceiling, stairs

office space with dark colored carpet and a high end fireplace Features: baseboards wall, natural light, drywall, office area, carpet, fireplace

carpeted home office with baseboards and a textured ceiling Features: vent, natural light, fireplace, baseboards wall, drywall, textured ceiling, office area, carpet

full bath with a garden tub, double vanity, light marble finish flooring, and a shower stall Features: marble finish floor, full bathroom, toilet, sink, drywall, shower, vent, double vanity, natural light, bath

bedroom with a textured ceiling and dark colored carpet Features: baseboards wall, carpet, natural light, textured ceiling, drywall

bedroom with a textured ceiling and dark carpet Features: carpet, natural light, baseboards wall, drywall, textured ceiling

bedroom featuring a textured ceiling, carpet flooring, ceiling fan, and a desk Features: drywall, office area, natural light, baseboards wall, ceiling fan, textured ceiling, carpet

carpeted bedroom with a textured ceiling and baseboards Features: carpet, textured ceiling, drywall, baseboards wall, natural light

staircase featuring a high ceiling, tile patterned floors, and hanging lights Features: tile floor, stairs, drywall, high ceiling, natural light, notable chandelier, baseboards wall

rec room featuring pool table and a community bar Features: billiards, basement, indoor bar

recreation room featuring light colored carpet, billiards table, and rail lighting Features: carpet, basement, drywall, billiards, track lighting, wood wall, baseboards wall

game room featuring billiards Features: billiards, drywall

indoor wet bar with wooden walls, a drop ceiling, dark colored carpet, dark countertops, and wood finish cabinetry Features: basement, carpet, wood wall, drop ceiling, medium brown cabinets, baseboards wall, countertops, indoor bar

indoor bar featuring a paneled ceiling, wood walls, carpet floors, and a glass covered fireplace Features: drop ceiling, fireplace, carpet, fire extinguisher, drywall, indoor bar, wood wall

game room with a drop ceiling and carpet Features: baseboards wall, drop ceiling, vent, carpet, basement, drywall

bathroom with a shower stall Features: full bathroom, shower

rear view of house featuring a fenced backyard, a wooden deck, a chimney, and brick siding Features: fence, lawn, deck, grill, chimney, brick siding, downspout

rear view of property with a fenced backyard, a chimney, a wooden deck, and brick siding Features: deck, grill, chimney, lawn, gutters, fence, brick siding, downspout

deck featuring outdoor dining space, grilling area, french doors, and a fenced backyard Features: lawn, fence, outdoor dining area, deck, grill, french doors

fenced backyard with a storage shed and a deck Features: fence, lawn, shed, deck, outdoor structure

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For Sale - 2203 Winding Woods Drive, Oakville, Ontario

2203 Winding Woods Drive

Oakville , Ontario

4 5 $2,549,000

Est payment $12,240/mo

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Time on Jump 5 day

AI Summary *

Rare opportunity on a private lot surrounded by nature and walking paths.
Spacious home with over 4,200 sq. ft. of above-grade living space.
Exceptional custom kitchen designed for cooking and entertaining in style.
Large lower level featuring a bar, snooker table, and space to unwind.
Convenient Tesla charger and mature landscaping for an enhanced lifestyle.

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Purchase Price

Term

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Down Payment:
$ 127,450 ( 5% )

First Time Buyer:
Yes No

New Build:
Yes No

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.

Listing IDW13064222

Address2203 Winding Woods Drive

CityOakville, Ontario

Price$2,549,000

Bed / Bath4 / 5 Full

Style2-Storey, Detached

ConstructionBrick

TypeResidential

StatusFor Sale

Extras

Subtype DetachedIndoor Features Auto Garage Door Remote, Central VacuumOutdoor Features Lawn Sprinkler System, Landscape LightingAmenities Electric Car Charger, Hospital, Park, Golf, Rec./Commun.Centre, Wooded/TreedOwnership FreeholdBasement FinishedFoundation UnknownHeating / Cooling Forced AirHeating Fuel GasSewer Sewer

Market Info

Parking 6.00

Listing Agency:
RE/MAX ESCARPMENT REALTY INC.

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Listing Agency:
RE/MAX ESCARPMENT REALTY INC.

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Hospital

Parks

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For Sale - 2203 Winding Woods Drive, Oakville, Ontario

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