5 Ontario Luxury Retreats from Old Oakville to Toronto Waterfront

Down a winding driveway on a private cul-de-sac in Springwater, this 1.52-acre offering sits within one of the area’s most prestigious estate communities, wrapped in mature oak and maple trees for a deeply secluded feel. The impressive 2-storey residence delivers over 4,200 sq ft of finished living space, where vaulted ceilings, a curved staircase, and refined finishes set an elegant tone. A formal dining room pairs soaring ceilings with a wood-burning fireplace, while the open-concept kitchen flows into a sunken family room warmed by a gas fireplace. A main-floor office adds everyday flexibility. Outdoors, the backyard reads like a private resort: a 20 x 40 saltwater pool, powered pool house, 18’ beam gazebo, hot tub, and professionally landscaped grounds with wrought iron fencing. A bright finished basement adds a gym, guest bedroom, and full bath for guests and downtime alike.

Size: 2,500 – 3,000 sf

Originally purchased over 40 years ago as a quaint cottage, this meticulously maintained 1.5-storey residence sits on a beautifully landscaped 50’ x 141.8’ lot in the heart of Old Oakville. Tucked away on a quiet, tree-lined cul-de-sac, it’s wrapped with inviting covered porches and decks—an easy place to slow down outdoors while staying close to everyday amenities. Thoughtfully renovated in 1992, the home offers generously sized principal rooms anchored by a sunken, oversized family room. Here, a reclaimed brick, wood-burning fireplace with a barn board mantel sets a warm tone, complemented by a matching bar and sliding doors that open to a Muskoka-inspired backyard. Expansive rear-facing windows bring in abundant natural light and connect to a spacious 36’4” x 14’6” deck for relaxed, year-round entertaining.

Size: 2,000 – 2,500 sf

Along the water’s edge at the end of a quiet, prestigious dead-end street, this private woodland retreat on Brambel Road pairs a serene 2-acre setting with access to Lake Simcoe. Spanning over 2,200 sq. ft., the residence blends rustic charm with modern touches, including a bright updated kitchen, hardwood floors, main-floor laundry/mudroom, and an updated ensuite. The newly finished 784 sq. ft. lower level (2023) adds flexibility with a games room, office, and cozy TV lounge. Outdoors, days unfold on the wraparound cedar porch with lake views or in the screened-in porch with a built-in BBQ kitchen. A charming 22×22 century log cabin studio offers space for guests, projects, or creative escape, while the sports court keeps play in motion with basketball, tetherball, and oversized chess and checkers. Life here feels easy, active, and quietly restorative.

Size: 2,000 – 2,500 sf

Along the water’s edge on spring-fed Buck Lake, this prestigious stone raised bungalow sits among more than 20 varieties of mature trees, set within the Canadian Shield. On the main floor, floor-to-ceiling windows and patio doors open to a wraparound deck, framing a clear 180-degree view across Crown land—including a direct sightline to Pulpit Island and the iconic “Devil’s Pulpit.” The walk-out lower level continues the connection to the landscape with its own floor-to-ceiling windows and patio doors, plus two additional bedrooms (with flexibility for a third), a 4-piece bathroom, a laundry closet, and a cozy rec room warmed by a propane fireplace. Step outside to the three-season space tucked under the deck, an easy place to linger over cards and games long into the evening.

Size: 2,000 – 2,500 sf

Along Toronto’s waterfront at Queens Quay East, Unit 401 at 29 Queens Quay E offers a bright, beautifully finished corner layout with lake views from both balconies. Soaring 10-foot ceilings and floor-to-ceiling windows bring in abundant natural light, while Acacia hardwood floors and upgraded light fixtures add a tailored feel throughout. The spacious living area opens to a fully upgraded kitchen with Miele appliances—including a gas cooktop, oven, microwave, and dishwasher—plus a Subzero fridge and wine fridge, pendant lighting, and a waterfall-edge breakfast bar. Two large bedrooms are complemented by heated floors in the primary ensuite and mirrored storage in the second bathroom, alongside a full-size Samsung washer and dryer. Freshly painted and truly turn-key, the residence also includes two side-by-side parking spots and two side-by-side lockers on P3. At Pier 27, resort-style amenities—from indoor and outdoor pools to a steam room, theatre, guest suites, dog wash, and car wash—round out everyday life.

Size: 1,400 – 1,599 sf