Toronto is a city of neighbourhoods — pockets of old-money glamour, new-money ambition, generational wealth, and street-car-suburbs that feel worlds away from the Bay Street even though they’re minutes from it.
Here are the neighbourhoods that sit at the top of the prestige pyramid — and why two non-downtown pockets, Riverdale and High Park, are actually where real people with real lives want to be.
The Bridle Path: Toronto’s Richest Neighbourhood, no contest.
Growing up, my mom and dad both referenced “ the Bridal Path” every time they spoke about the richest of the rich. They both lived downtown for a portion of their lives, and they and their peers all agreed.
The Bridle Path is the richest neighbourhood in Toronto, with average home prices regularly floating in the $6M–$20M+ range. This is where estates come with driveways longer than some downtown streets and where 20,000-square-foot homes sit on lots that feel more like private parks.
Why it’s prestigious:
- No sidewalks, no through traffic, no chaos.
- Massive lots, custom estates, security gates, and an unspoken culture of “you don’t ask what people do for a living.”
- Proximity to Edwards Gardens and the ravine systems gives it that rare country-in-the-city vibe.
Who lives (or has lived) here:
- Drake (the one everyone knows — his mansion is practically a landmark)
- Prince (yes, Prince once owned a home here)
- Gordon Lightfoot
- Celine Dion
- The Westons & The Lauders
- Who can forget Conrad Black’s episode outside of his gates?
The Bridal Path isn’t just about the homes; it’s the proximity to the best private schools & Private clubs in Toronto.
Three exclusive clubs the affluent want to be a part of:
Three incredible schools close by:
Toronto is home to some world-class educational institutions. Wondering where to find them? Read: Where to Find the Best Private Schools in Toronto
Forest Hill
Forest Hill is old money done quietly. Growing up, my good friend, Ashley, used to live in the old Eaton House On Old Forest Hill Road – we regularly enjoyed the basement grotto with peek-a-boo-window. I regularly saw all of the kids get driven around by nannies while moms spent their entire days at restaurants and beauty salons – ah the life!
Something very cool about Forest Hill is that it used to be part of a separate village but was later amalgamated into Toronto in 1967. I’ve always loved the larger-than-life trees that line the streets and the oversized lots they peer from.
The area is home to two of the city’s top Private Schools, both within walking distance to most homes.
Forest Hill is fabulously walkable and connected to multiple forms of transit. It’s walking distance to Yonge and Eg and can be considered a perfect blend of exclusivity and urban living.
Learn more about living in Forest Hill by reading our comprehensive community guide.
Do you still have questions about Toronto’s best neighbourhoods? Here are a few more posts about some of our favourites:
- Is Cabbagetown a Good Place to Live?
- Why Leslieville is a Great Toronto Neighbourhood to Raise a Family
- 10 Reasons Why Parkdale Will Never Gentrify
Rosedale
Rosedale is one of the oldest and most beautiful neighbourhoods in Toronto — a maze of winding roads, ravines, heritage mansions, and century homes with perfect symmetry. Many of the homes are designated heritage A and B, meaning their exteriors can’t be changed. Rosedale revels in the Old Money sentiment, and conversations tend to revolve around Muskoka, Hedge Funds and St Barts. During the day you’ll find Rosedale park full of nannies, mom’s in ALO, & and that one stay-at-home-dad who everyone’s confused by.
Why it’s prestigious:
- Ravine lots that feel impossibly private while being minutes from Yonge and Bloor
- Protected heritage homes (half of them are heritage B now)
- A long-standing reputation as the hub of the city’s political and philanthropic class
Famous/Notable residents:
- Margaret Atwood
- Ken Thomson family connections
- The Munk Family
- Adrienne Clarkson
Rosedale’s walkability isn’t the best compared to other parts of the city but it does have Castle Frank and Rosedale Subway Stops on its perimeter. On top of the subway that no one in Rosedale actually uses are three incredible public/catholic schools.
Wondering what it’s really like to live in Toronto’s Rosedale neighbourhood? Read our community guide for a closer look.
Why Riverdale and High Park Are Actually the Best Neighbourhoods for Real People.
My take: Prestige is one thing but livability is another. If your budget doesn’t quite hit the 3m + mark your next best bet is Riverdale or High Park.
Riverdale: (I’m obviously Biased)
Riverdale is one of the few Toronto neighbourhoods where you get impeccable Victorian/Edwardian homes, massive parks, top public schools, and a true sense of community — without sacrificing commute or cool factor. I like to say that people in Rosedale buy art & people in Riverdale sell it to them. This neighbourhood is home to Doctors, Lawyers, Hedge fund owners who are still friends with teachers, actors, and city workers.
Why it’s one of the best non-downtown neighbourhoods:
- Riverdale Park East and the skyline view that never gets old
- Phenomenal school catchments, including Frankland, Withrow, Jackman, and Montcrest Private School.
- Withrow Park – a massive space in the center of the neighbourhood.
- One-way streets with large leafy trees
- Retail inside the neighbourhood streets.
- On the subway line and two streetcar lines.
- Just outside the future Ontario Line hub at Pape.
- All the retail and commercial you could ever need on Danforth.
Riverdale has that mix of grit-turned-gorgeous that feels authentically Toronto and incredibly connected. Learn more about why we live it by reading our neighbourhood guide.
High Park:
My mother’s family came to Toronto from Poland in the early 1950s settling in Queen West. On the weekends they would all go down to St Stan’s parish on Roncesvalles and eat at the Polish bakeries across the street. The neighbourhood was bustling with European flair and much of that still stands today.
Why I love High Park:
- People live here FOR LIFE – low turnover.
- The mom groups are ample and strong!
- The massive park itself — trails, ponds, the zoo, sports fields
- Turner-of-the-century homes full of character
- The best bakeries and coffee shops in the city
- Quick Walk to Sunnyside Beach and The Lake.
- Roncesvalle Polish Festival
- Easy commute on the Bloor subway line
- High park is also home to top public school Garden Ave Junior School.
High Park is where people move when they want space, greenery, and stability but still want the Toronto lifestyle — coffee walks, vintage shops, bakeries, and great schools.
Whether you’re looking for home-buying, selling, or relocating advice, I’m always happy to help. If you have questions, I have answers. Get in touch today by filling out the form on this page, calling me at 416-728-5401, or emailing me directly at ddemerino@royallepage.ca.
