Tucked behind wrought iron gates in Forest Hill, Yorkville and The Bridle Path, life hums along quietly for Toronto’s ultra-wealthy, and it’s a version of the city that few average residents will ever see, let alone experience.
While most of us are budgeting for our next grocery run or checking the TTC schedule, there’s another Toronto, one where grocery stores stock your fridge without you knowing, cottages are reached by private floatplane and social standing is as much about your art collection as it is about your dining table.
These insights come from a remarkably candid discussion on Reddit’s r/AskTO thread, where users swapped stories of Toronto’s richest and their surreal routines. The comments, though anecdotal, paint a vivid picture of a lifestyle that’s usually kept well out of public view, behind hedges, doormen and gated driveways.
Personal shoppers and key access groceries
According to Redditor u/Fun-Ad-5079, the wealthy don’t just buy luxury, they often delegate the entire experience. “A person goes to a store like Hermès for their client, to deal with a customer service rep whose whole job is to deal with personal shoppers.” That same commenter described a service at Pusateri’s where “they hand over a key to their house so that the grocery store can constantly come in and stock their fridge.”
Pusateri’s, one of Toronto’s most upscale grocers, confirmed to Toronto Life in 2022 that concierge-style services, including personalized grocery lists, pantry restocking and even in-home fridge organization, are indeed available for a very exclusive clientele.
It’s a level of convenience that stands in stark contrast to the reality most Torontonians are experiencing. Food inflation, while cooling slightly in 2025, has left a mark. According to Statistics Canada, prices for many essentials are still up over 21% since early 2022. For the average household, that’s meant more careful shopping, meal planning and prioritizing value over indulgence.
But for the city’s wealthiest, groceries are a background task, often completely invisible. A fridge simply stays full, curated to taste, no shopping list or trip to the store required.
While this may sound extravagant, it’s also a reminder of how differently time and daily routines are managed across economic lines. Where some families might carve out Sunday afternoons for errands and prep, others outsource it all, creating time for leisure, travel or other pursuits.
This kind of lifestyle isn’t about flaunting wealth so much as eliminating friction. And while it might seem far removed from everyday life, it offers a glimpse into how the other half not only lives , but navigates the city with a fundamentally different relationship to time, convenience and choice.
A second home, for guests only
Imagine owning not one, but two homes in one of the most competitive real estate markets in Canada, and using one of them strictly for entertaining. Redditor u/Automatic_Contract47 shared, “I have a client who has a second house in Yorkville just for entertaining his friends.” He added that the same client brings in Michelin-starred restaurants to cater family holidays.
It may sound like something out of a Netflix series, but among Toronto’s ultra-wealthy, keeping a secondary residence solely for hosting is more common than one might expect. In neighbourhoods such as Rosedale, Forest Hill and Yorkville, real estate isn’t just about shelter or even investment, it’s also about lifestyle design.
While most homeowners are contending with rising mortgage rates or limited square footage, Toronto’s most affluent families often treat real estate as a tool for flexibility and freedom. These extra homes can be used to host business associates, accommodate extended family or simply offer a change of scenery without leaving the city.
And it’s not just local. Many high-net-worth individuals quietly maintain properties in cities around the world — New York, London, Dubai and the Caribbean are common examples. It’s part of what some wealth advisors call a “global lifestyle portfolio,” where real estate functions as both a financial asset and a passport to privacy, comfort and exclusivity.
While this level of luxury may be out of reach for most, it offers an interesting perspective on how differently people use space when money is no object. For some, a second home means escaping the city; for others, it means opening their doors — in style — to a curated guest list.
The art of money — literally
For some Toronto elites, wealth isn’t just about consumption, it’s also about creation, though appreciation can be as much social as artistic. Redditor alexwblack shared an intriguing story about an affluent couple: “The wife… considered herself quite an accomplished visual artist.” While the work was described as “objectively poorly made,” it still sold for five figures, primarily to friends within her social circle.
“She’s probably making well over six figures annually from this charade,” the commenter joked. Her pieces now hang alongside works by established artists, which can help boost their perceived value in the closely knit art communities of Rosedale and other high-end Toronto neighbourhoods.
This phenomenon isn’t just about taste, it also has economic dimensions. In Canada, art can be a savvy investment. According to the Canada Revenue Agency, donating artworks to registered charities can offer significant capital gains tax advantages, encouraging collectors to strategically manage their portfolios through art.
For Toronto’s wealthy, art often functions as both a passion project and a financial asset, blending creativity, social signaling and investment. It’s a reminder that, in the city’s elite circles, value isn’t always what it seems on the surface.
Social clubs and ski resorts you’ll never hear about
Beyond the boardrooms and brunches, Toronto’s wealthy have their own exclusive playgrounds — social clubs and private resorts where membership fees can be as steep as the experience is rarefied. Redditor u/CSW11 summed it up: “Private social clubs, annual dues too. Yacht clubs, golf courses, wine clubs, etc.”
Places such as The Boulevard Club or the Rosedale Golf Club come with initiation fees that can top $30,000, and memberships are strictly by invitation only. These aren’t just venues; they’re private communities where relationships are forged over a shared appreciation for luxury, privacy and tradition.
And it’s not just the city. As u/red-et pointed out, Toronto’s elite escape to “private ski resorts in the winter.” This isn’t your typical Blue Mountain weekend getaway. We’re talking about private heli-skiing charters and ski hills owned collectively by a select few families, offering seclusion and prestige that go far beyond the public slopes.
These hidden social circles highlight how Toronto’s wealthiest not only live differently but play differently, in spaces and experiences that most of the city might never even know exist.
Floatplanes, filet mignon for dogs and doctors on call
Wealth has a way of transforming even the most everyday tasks into something extraordinary. Redditor futuresobright shared, “My friend said he’s never shovelled a driveway in his life,” highlighting how luxury often means delegating chores that most of us tackle ourselves.
Another Redditor, tayims, described a family that hasn’t driven to their Muskoka cottage in “like 15 years,” instead opting to charter floatplanes directly from Billy Bishop Airport. “On big weekends they will charter about 3 or 4 trips up and the same back for guests,” making what many consider a long weekend getaway feel effortless.
And then there’s the finer, more surprising details of this lifestyle: dogs eating filet mignon, as Top_Currency_6204 noted, weekly visits from live pianists and florists (Fun-Ad-5079) and even a wealthy couple who hire their doctor to travel with them on vacation (Hanlans_Dreaming).
These anecdotes offer a glimpse into how the ultra-wealthy blur the lines between convenience, indulgence, and care, turning everyday moments into experiences that feel more like a luxury service.
Not just new money: Generational influence
When we think of Toronto’s wealthy, it’s easy to picture flashy displays and fast fortunes. But the city’s “old money” operates with a different kind of quiet power — one built on deep relationships and lasting influence.
One Redditor shared a vivid story about their friend’s grandmother, a longtime patron who generously donated to institutions such as the Royal Ontario Museum and the University of Toronto. “Her dinner parties were brilliant,” the user recalled. “She would show up on a Friday night without a reservation at a super fancy place… and the head chef would come out and hug her.”
This anecdote highlights a key layer of Toronto’s wealth: It’s not just about money, but social capital that’s been cultivated over generations. It’s the trust, respect and connections that open doors, smooth paths and create a legacy that extends well beyond bank accounts.
In Toronto, generational wealth quietly shapes the city’s cultural and philanthropic landscape, weaving influence into institutions and communities in ways new money often can’t replicate.
The hidden currents shaping Toronto
At first glance, this peek into the lives of Toronto’s wealthiest might seem like nothing more than harmless curiosity. But understanding these hidden worlds reveals something deeper: how wealth quietly reshapes the city itself.
From soaring property values and philanthropic power plays to exclusive healthcare access and tax strategies, these subtle luxuries ripple across Toronto’s urban fabric in ways most don’t see. They influence everything from neighbourhood dynamics to cultural institutions, creating layers of experience within the same city.
So the next time you pass a discreet Yorkville doorway or spot a floatplane gliding over Lake Ontario, remember — there’s another Toronto beneath the surface. One that lives differently, moves differently and plays by a set of rules few ever glimpse.
Sources
1. Reddit: r/AskTO: What’s something the rich people in Toronto do that the average person has no clue about?
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
