5 Ontario Homes with Pools, Ravines, and Heritage Charm

On a desirable Clarkson street in South Mississauga, this renovated sidesplit pairs everyday ease with a rare, trail-backed setting. An addition expands the layout with a bright, spacious family room anchored by a corner gas fireplace and built-in cabinetry with a beverage fridge and serving area—made for movie nights, sporting events, and holiday gatherings. Wide-plank hardwood runs through the refreshed interiors, while the centre-island kitchen is finished with quartz counters and GE stainless appliances. Upstairs, a renovated 4-piece bath serves three bedrooms. Downstairs, a finished basement offers additional bedroom or recreational space, plus generous storage. Outside, new siding and front windows, a repaved drive (2024), and beautiful landscaping with tall trees set the tone, while a composite deck overlooks a concrete inground pool and greenspace with walking trails—an easy rhythm for indoor-outdoor living.

Set on a beautifully landscaped, just over 1/2-acre lot in one of New Hamburg’s most sought-after neighbourhoods, this bungalow balances everyday ease with room to stretch out. The main floor centers on a spacious primary suite with a coffered ceiling, walk-in closet, and updated 5-piece ensuite, alongside a second bedroom and engineered hardwood flooring. A bright living room with a gas fireplace flows to a spacious kitchen and dining room, with main-floor laundry and a double garage adding welcome practicality. Downstairs, the finished lower level is designed for flexibility: a large rec room with a second gas fireplace, a second kitchen, two additional bedrooms, an office, an updated bathroom, and abundant storage—ideal for extended family or guests. Outside, a composite deck, wraparound porch, hydro-equipped shed, and pool-sized backyard invite unhurried afternoons.

Sheltered by Cootes Paradise, this one-of-a-kind century home pairs a rare 236-foot-deep lot with an enviable Westdale setting. Inside, the layout is notably flexible, offering 4+4 bedrooms, 2.5 baths, and two kitchens—an arrangement that invites a range of living possibilities while preserving the character implied by its century roots. Daily life here is defined as much by what’s beyond the front door as what’s within: McMaster is just steps away, along with local shops, cafés, and nearby trails that make it easy to slip into a walk, a coffee run, or a campus commute. Set within one of the area’s most picturesque neighbourhoods, it’s a property that feels connected to nature and community in equal measure, with room to imagine what comes next.

Set on 10 acres in the historic hamlet of Belfountain, this move-in-ready bungalow sits well back from the road on elevated land with westerly views of the Caledon Hills. The outlook is pure country calm: a pond, an inground cement pool, and perennial gardens carefully tended by the original owner. Inside, three bedrooms include a primary suite with a walkout to a large balcony overlooking the pond and pool. A walkout basement connects daily life to the landscape, opening toward the back paddocks and hobby-farm setting. For those drawn to land stewardship, the property includes a barn with water and power, storage for hay, and four independent paddocks, along with rolling terrain and trails. Quaint shops and food services are a 15-minute walk away, with the Bruce Trail and nearby trail systems close at hand.

Size: 1,500 – 2,000 sf

In the heart of West Oakville, this cherished one-and-a-half-storey residence has been held by the same owners for nearly 30 years, offering nearly 1,500 sq. ft. above grade and a layout that adapts to changing needs. Two upper-level bedrooms and a versatile den are complemented by a main-floor bedroom, two bathrooms, and a finished basement with additional living space, laundry, and ample storage. Set on a generous 45′ x 135′ lot in an established neighbourhood surrounded by impressive new construction, the property invites plans to renovate, expand, or build anew. Mature gardens, an exceptionally private backyard, and a convenient U-shaped driveway add immediate ease, while the deep lot suggests room for outdoor entertaining and future possibilities. Daily life is well-situated near schools, parks, transit, highways, Oakville Place, and Downtown Oakville.