5 Ontario Luxury Listings, from a Private Island to Yorkville Heights

Along the water’s edge in Lake Huron’s North Channel, Picture Island offers a private 47.6-acre setting downstream of Sault Ste Marie, near St Joseph Island and beside Campment D’Ors Island off Kensington Point. Nestled atop a 100-foot rock cliff, the cottage and separate bunk house were designed for large family gatherings, with north-east facing vistas over the channel. The main house centers on open-concept living: a large kitchen, dining area, and living room anchored by a wood-burning fireplace, plus a library and media room. A screened-in porch and outdoor kitchen extend the day outdoors, while more than 3,000 square feet of decks link the buildings. The bunk house adds four large bedrooms, two bathrooms, and a screened porch for each room. A winding road leads to a floating dock in a protected cove, with game trails and abundant wildlife beyond.

Size: 47.6 acres

Price: $2,999,900 USD | $3,999,900 CAD

Rising high above Toronto in the heart of Yorkville, Suite 3802 at 200 Cumberland Street frames the city through floor-to-ceiling windows with panoramic skyline views day and night. Designed by Thomas Pearce Interior Design, this executive residence layers globally sourced luxury materials with carefully curated detail, from Giorgio Collection furnishings and rugs selected in Milan to custom Murano and Baccarat light fixtures. A rare 12-foot custom fireplace anchors the living space, complemented by a distinctive kitchen backsplash by internationally renowned artist Rob Baylor and striking Costa marble installations that read like gallery pieces. Sophisticated custom bronze detailing, architectural millwork, wrapped leather columns, and handpicked hardware add depth throughout, while state-of-the-art home automation offers intuitive control. An enclosed private garage with six spaces—including one with an EV charger—plus three private lockers completes the experience, alongside five-star amenities from concierge and valet to a rooftop terrace.

Size: 4,000 – 4,249 sf

Set on ~1 acre in Erin, this exceptional estate balances luxury with everyday function across 8,234+ sq ft. Ten-foot ceilings amplify the sense of scale, while an open-to-above great room creates a natural gathering point around a stone fireplace. The chef’s kitchen is designed for both serious cooking and easy entertaining, with high-end appliances, an oversized island, and a butler’s pantry, plus a walkout to a large deck for seamless indoor-outdoor flow. A main-floor primary retreat brings comfort and privacy, complete with a spa-like ensuite and walk-in closet. Downstairs, a finished walk-out basement extends the living space with a rec room, gym, and wet bar. Geothermal heating and premium upgrades throughout underscore a thoughtful, future-minded approach to estate living.

From its hilltop setting in sought-after Glen Major, this nearly 22-acre private estate pairs protected forest with rolling fields, reached by a winding, tree-lined drive and set minutes from Claremont and Hwy 407. Inside, arched mahogany double doors open to a dramatic great room with 18-foot coffered ceilings, statement lighting, floor-to-ceiling windows, and a soaring cast-stone fireplace, grounded by mahogany hardwood and rich millwork. The chef’s kitchen is anchored by a 60-inch Wolf dual-oven range, cabinet-matched Dacor fridge and freezer, and premium Miele appliances, with an oversized island and walkout to the deck and gazebo. A hidden pantry links to the formal dining room overlooking a fire-and-water feature and cherry blossoms. A finished lower level adds a self-contained one-bedroom suite, theatre, gym, and games room, while resort-style grounds include an inground pool, cabana, orchards, and landscape lighting.

Size: 22.00 acres

Steps to Lake Ontario in the heart of Roseland, this custom 3+1 bedroom, 4+2 bath residence balances timeless craftsmanship with a distinctly modern point of view. Just under 6,000 square feet of living space unfolds from a foyer defined by a natural stone feature wall and an open staircase—an architectural moment that sets the tone on arrival. The layout is designed to feel expansive yet composed, with details that speak to the care behind a truly bespoke build. With multiple baths and flexible bedroom count, the home supports both everyday routines and a more generous rhythm of hosting and retreat. Outside, the setting places Burlington’s shoreline within easy reach, bringing the lake into the cadence of daily life. It’s a home that invites you to settle in and stay awhile.