5 Ontario Trophy Listings: Waterfront, Island Lots, Estates, and Development

Along the water’s edge in Burlington, this extensively updated waterfront residence unfolds across more than 6,900 square feet of total living space, thoughtfully arranged for flexible living. Six bedrooms and 4.5 baths are complemented by three self-contained living spaces—an ideal setup for multi-generational households seeking both connection and privacy under one roof. Set on a rare 93 x 313 ft lot on the bay, daily life is framed by breathtaking views and an easy relationship to the outdoors. Private docking anchors the waterfront experience, while exceptional outdoor living invites long, unhurried afternoons by the water and evenings spent watching the light change across the bay. It’s a home designed to accommodate evolving needs while keeping the shoreline at the center of every day.

Along the water’s edge on Campbell Island in the Township of The Archipelago, this rare offering spans five legally severed lots, each with service road access and elevated building sites with sweeping views to the outer islands and the open water. Three natural harbours with docks set the tone for a true island compound. Lot #2 is a turnkey retreat, anchored by a spacious main cottage with a loft master suite and private balcony. The main floor is designed to live outdoors, with walk-outs from every room to a wraparound deck, complemented by a top-end chef’s kitchen, a full wet bar, and an outdoor kitchen. Two self-contained guest cottages accommodate eight to ten, while a full workshop, utility and mechanical buildings, a drive shed with motorized utility vehicles, and a protected harbour with stone breakwater and marine shed complete the experience. Everything is included, aside from sellers’ personal effects.

In the heart of Richmond Hill, this city-approved, shovel-ready infill project at Bathurst St & King Road offers a rare chance to shape a lasting residential enclave. Approval is in place to build nine homes, including four semi-detached residences and five detached homes with double garages, creating a thoughtful product mix designed for everyday living. Municipal servicing and sanitary connections are available, with water allocation already secured, streamlining the path from vision to build. Set on a quiet street surrounded by custom-builts, the setting feels established and family-friendly, with easy access to highway routes, transit, shopping, top-ranking schools, golf courses, parks, and trails. With no rezoning risk and potential upside tied to city infrastructure incentives, it’s a framework for a community that can grow into its surroundings over time.

Size: 1.00 acres

Down a winding tree-lined drive in sought-after Glen Major, this nearly 22-acre private estate pairs protected forest with rolling fields, just minutes from Claremont and Hwy 407. The hilltop residence has been extensively redesigned and renovated, introduced by arched mahogany double doors and a dramatic great room with 18-foot coffered ceilings, statement lighting, floor-to-ceiling windows, and a soaring cast-stone fireplace. Mahogany hardwood and rich millwork continue into a chef’s kitchen anchored by a 60-inch Wolf dual-oven range, cabinet-matched Dacor fridge and freezer, premium Miele appliances, and an oversized island, with a walkout to the deck and gazebo. A hidden pantry connects to the formal dining room overlooking the fire and water feature and cherry blossoms. Resort-style grounds include an inground pool with deck jets, cabana, orchards, and landscape lighting for long, unhurried days at home.

Size: 22.00 acres

On a quiet stretch of coveted Carnwath Crescent in prestigious St. Andrews-Windfields, this custom residence unfolds with thoughtfully designed living space and over 5,000 square feet of total finished area. Hardwood flooring runs throughout beneath 9’, 10’, and 9’ ceilings, while three fireplaces add warmth and rhythm to daily living. At the center, a custom chef’s gourmet kitchen—anchored by a natural stone island—opens to a grand, bright kitchen and family room, with a breakfast area framed by a bay window and a walkout to the garden. A wine fridge and private main-floor office support both entertaining and focused workdays. Upstairs, the primary retreat pairs a 5-piece ensuite with a lavish boudoir. The walk-up lower level adds a gym, fifth bedroom, and spacious recreation room for flexible living year-round.

Size: 3,500 – 5,000 sf