Ultra-luxury living has taken off in Canada, with astronomically-priced condo penthouses rising majestically in the plush skies high above the masses in major urban centres across the country. 

A perusal of recent offerings in Toronto, Vancouver and Montreal tells the opulent tale of the demand for affluent downtown living: the 5,860 sq.-ft. double penthouse at The Ritz-Carlton Residences in downtown Toronto is currently listed at $22.5 million; the 8,000 sq.-ft. multi-level penthouse at the swanky Three Harbour Green in Vancouver’s prestigious Coal Harbour neighbourhood is listed at $39 million; and the 6,979 sq.-ft. “Rockstar” penthouse in Montreal’s Ritz-Carlton Residences, in the city’s historic Golden Square Mile, went for a cool $12,900,000 in 2021. 

The air above has become so rarefied that when former prime minister Justin Trudeau recently purchased an “expansive estate in Montreal’s exclusive Outremont neighbourhood” for $4.26 million, the price seemed almost paltry in comparison. Still, the 4,965 sq.-ft. century-old stone dwelling fixer-upper – with seven bedrooms, five bathrooms and a lavish ballroom – should be sufficient to satisfy girlfriend, pop-star Katy Perry, and is certainly a step up from his old digs at the rapidly dilapidating Rideau Cottage, his official residence while in office. However, he might have to ask Perry to hit the road again to fund the purchase, her latest Lifestyles tour grossed a reputed $134 million, enough to send her on another rocket back to space, but for a truly stratospheric lifestyle, she might have to think bigger – we propose a Billionaire’s Lifestyles tour.

This demand for luxury living persists despite the economy’s well-documented struggles. With companies laying off staff and paying wages that aren’t keeping pace with inflation, the top-end real estate market is being fueled by new-money tech billionaires or old-money families. Not to mention corporate titans: in 2024, the average pay for the top 100 CEOs in this country reached a record $16.2 million (compensation plus bonuses) – 248 times that of the working stiff’s average salary. For example, Shopify’s Tobias Lütke, the highest paid CEO in Canada, earned $205.5 million in 2024. 

Toronto developers Peter Politis and Sasha Cucuz are gambling they won’t have trouble finding a one-percenter to ante up for the most expensive condo dwelling ever listed in this country – the $83 million luxury super-penthouse (a truly massive space – 14,000 sq. ft. inside and 6,000 sq. ft. outside) at the top of the planned 31-storey 138 Yorkville building in the heart of the swish Toronto neighbourhood after which it’s named.

”We want this to be one of the most pre-eminent buildings in the world,” explains Politis, CEO at Greybrook Realty Partners, the developers behind 138 Yorkville, during our visit in December. “We’re bringing something new and unique to a city that, to be frank at this point in time, deserves it,” agrees his business partner Cucuz, a former pro hockey player who went on to become CEO at Greybrook Capital.

So who can afford to live in this mansion in the sky? “We joked that the super penthouse is for Bruce Wayne,” says Politis. “It’s for someone who’s going to feel like the king of Toronto, looking over their entire kingdom.”

If Bruce Wayne’s not available for the planned autumn 2028 opening of 138 Yorkville, here are our picks for Canada’s top super-wealthy condo contenders.  

Drake

Drake might move in for The Vault alone. He could custom-design the state-of-the-art German-made safe room to house his formidable watch collection, which reportedly includes Richard Mille, Audemars Piguet, and more than 143 Rolexes. Each watch can be placed on one of The Vault’s custom winders that can be programmed to rotate in the right direction and speed for that particular model. The walls of the vault are so thick – it weighs about the equivalent to five Range Rovers – it could burn for seven days, and it would still be intact. 

Elon Musk

With 14,000 square feet of living space that can be configured almost any way an owner desires, there would also be plenty of room for tech billionaire Elon Musk and his estimated 13 to 14 children. He could no doubt overcome the foreign buyer’s tax by playing his Canadian citizenship card (Musk is South African and American as well). The glass room on the penthouse’s roof could easily accommodate a formidable telescope, allowing him to keep an eye on his SpaceX program — if he tires of watching rockets launch from his phone. Or perhaps serve as a dormitory for his many nannies (at one point he had at least six).

Joseph Tsai

Taiwanese-Canadian billionaire and Alibaba Group co-founder Joseph Tsai is famously discreet – so discreet, in fact, that no-one is quite sure whether he has even lived in Canada (he became a naturalized citizen through his parents). The stealth-wealth features of 138 Yorkville would likely appeal: an underground lower-lobby pickup for his car means no awkward waiting in a public valet area; there is a dedicated service elevator for everything from food deliveries to the Alibaba parcels; and there are no shared walls or common spaces with neighbours. Tsai is no stranger to eye-watering property prices, the firm that manages some of his and Alibaba co-founder Jack Ma’s fortune, paid US$188 million for Daniel Och’s penthouse at 220 Central Park South (the second-most expensive in Manhattan). That’s on top of the two units he bought in Central Park South’s Robert A.M Stern building for US$157 million. 

Lance Stroll

This condo could also serve as a rather glamorous crash pad for Lance Stroll, the 27-year-old son of fashion billionaire Lawrence Stroll. With ramps designed for the delicate proportions of supercars, Lance – currently a driver for the Aston Martin Aramco F1 team – wouldn’t have to worry about bottoming out while parking his Lamborghini Huracán (worth roughly $500,000). His father, meanwhile, could drop by in his ultra-rare 1967 Ferrari 275 GTB/4 NART Spider, purchased for a record-breaking US$27.5 million.

Tobias Lütke and Fiona McKean

Shopify founder Tobias Lütke and his wife, Fiona McKean, might also find the building appealing. The couple left McKean’s native Ottawa for Toronto in 2023, though they are hardly stereotypical tech billionaires and eschew flash. Lütke, who was chosen to moderate a conversation with former U.S. President Barack Obama in Ottawa in 2019, stated his cheat code for life is to “read books.” However the building’s green credentials could appeal to them – McKean founded the Thistledown Foundation to accelerate carbon-removal technology and mitigate the worst impacts of climate change. One of 138 Yorkville’s most unusual features is its staggered terraces, each designed to host trees – a complex feat of engineering. The super penthouse’s vast 6,000-square-foot terrace will contain 13 trees alone, which will live in smart planters that monitor and relay information about each tree’s health and needs. Architect Brian Brisbin says the building will “create a sustainable microclimate of its own,” explaining that the terraces were designed “to host a forest.” The trees add texture, reduce noise pollution, and lend the tower a lush, vertical greenery.

Mark Scheinberg

The pet spa – with its multiple dog-washing stations, grooming area, and drying facilities – would be particularly useful for PokerStars co-founder Mark Scheinberg. He established the Scheinberg Relief Fund, which lists animal welfare as one of its four key pillars, and he frequently posts about his dogs, rescued through his brother Rob Scheinberg’s Dog Tales, a dog and horse rescue set on 100 idyllic acres near King City. At the sanctuary, each dog has its own room, with beds made out of antique dressers, books and art, as well as a personal chef, so for city stays with their uncle, the super penthouse should be on par.