Five properties currently available near Toronto’s famed Bridle Path — for those who listened to ICEMAN and felt inspired.
On 15 May 2026, Drake dropped three albums simultaneously, set a Spotify single-day streaming record, and reminded the world — not for the first time — that he is Toronto. Not just from Toronto, but architecturally, spiritually, and geographically embedded in the city in a way few artists ever manage. The Embassy, his 50,000 sq ft limestone estate on Park Lane Circle, was always as much statement as home. It has its own basketball court, a Murakami-designed piano, and a great room with 44-foot ceilings. Aubrey Graham doesn’t do things quietly.
Which raises a reasonable question for the globally mobile buyer who has Toronto on the mind: what would it actually cost to move in next door?
The Bridle Path — affectionately known in local parlance as Millionaires’ Row — occupies a stretch of ravine-bordered estate land in North York, about thirty minutes from downtown. It is one of the few neighbourhoods in Canada where the lots run to acres rather than metres, where mature oaks press against the windows of houses built for entertaining at scale, and where the prevailing sound is, in fact, silence. Celine Dion lived here. Prince spent time here. The area has long understood a certain kind of famous.
Five properties are currently available through Sotheby’s International Realty — each one a different proposition, each priced for someone who has already made their money and is now thinking about where to put it.
338/340 Riverview Drive — CAD $10,995,000
Tucked into a majestic cul-de-sac in Teddington Park, directly on the edge of Rosedale Golf Club, this 7,386 sq ft, six-bedroom residence sits on nearly an acre of gated land with 229 feet of frontage. The outdoor space is anchored by a saltwater pool and a deck cantilevering over the ravine. Inside: soaring triple-scale living room, a billiards room off the main floor, and an octagon-shaped home office wrapped in windows — the kind of room that makes working from home feel like a character trait rather than a compromise. Available separately or combined with the adjacent lot. View listing →
28 Glenorchy Road — CAD $10,980,000
French Châteauesque in the truest sense — a Hovan Homes masterpiece set above Glendon Forest and Sunnybrook Park, with a 25-foot foyer ceiling anchoring a symmetrical layout designed around the kind of entertaining that requires gallery-style hallways and a hand-painted library. Curved staircases, silk fabric walls, segmental arches. Just under 7,400 sq ft across four ensuite bedrooms above grade, with a walkout lower level for staff or guests. It sits close to the Granite Club, the Toronto French School, and several of the country’s better private schools — which, in Bridle Path terms, is simply the done thing. View listing →
23 Country Lane — CAD $13,998,000
A seven-bedroom, eight-bathroom estate on one of the Bridle Path’s quieter residential lanes, listed through Sotheby’s. Country Lane sits within the enclave’s inner geography — a street where properties rarely surface and rarely need to advertise loudly. At just under $14 million, it occupies the middle ground between the neighbourhood’s more accessible offerings and its full-scale châteaux: substantial enough to belong, understated enough to be interesting. View listing →
45 Bayview Ridge — CAD $22,500,000
Designed by Gordon Ridgely and set on 3.12 acres of double lot, this French château is what people mean when they say a property commands its setting. The facade spans almost 150 feet of Indiana buff limestone and rubble stone beneath Vermont slate shingles, with an ivy-clad turret that gives the house its unmistakeable silhouette. The grounds — designed by Ron Holbrook — include a negative-edge infinity pool, a reflecting pond with stepped waterfall, kitchen gardens, stone terraces, and a tennis court. Inside, 15,000 square feet of living space runs to Brazilian cherry wood floors with African wenge inlay and acid-etched Crema Marfil marble. This is a property that arrived with its own mythology. View listing →
52 Post Road — CAD $22,980,000
And then there is Post Road. Over 25,000 square feet of European Neoclassical architecture — high arched doorways, wrought iron staircases, 23-foot ceilings, marble floors laid in intricate pattern. The listing describes a ballroom with capacity for 300 guests. Three kitchens. Twelve bathrooms. It reads like a Versailles footnote that somehow wound up in North York, which is precisely the point: this house was built to make a statement in a neighbourhood already fluent in statements. Drake’s Embassy is impressive. Post Road is a conversation about what impressive means. View listing →
Toronto rarely presents itself as an obvious luxury destination for the international buyer — it doesn’t have the climate mythology of the Côte d’Azur or the status shorthand of a Mayfair postcode. What it has instead is scale, privacy, a genuinely world-class city running quietly beside these ravines, and, as of last Friday, the world’s most-streamed album of 2026 recorded somewhere inside a house on Park Lane Circle.
The Bridle Path doesn’t need to sell itself. Neither, it turns out, does Drake.
Demeure. 
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