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East Side

West Side

North of Bloor

Suburbs

East Side

You’ll notice pretty quickly that Toronto’s East Side is more affordable than the West Side. This is because the East Side was closest to — and often upwind of — the industrial Port Lands. As a result, the East Side has been traditionally working class.

Bay Street: The Financial District

Yes, this Financial District is just as quiet as the one in New York after a certain hour. However, it’s a better fit for downtown Chicago, thanks to its near-complete reliance on the PATH for street life.

The Beach: Rockaways + Sheepshead Bay

If you’ve been to the fancy areas of the Rockaways, you know what we mean. The slowness of the Queen Car at rush hour gives it a similar commute.

Cabbagetown: Ditmas Park

You’ll find a little bit of everything on Parliament, the main drag through Cabbagetown. There’s enough to do, but not a lot to do. There’s a handful of restaurants, small shops, and a few grocery stores, just like what you’d find on Cortelyou Ave in Brooklyn. Lots of renovated single family homes next to larger apartment complexes mean that the neighborhood is a nice mixture of people.

Corktown & Distillery: Meatpacking

These old breweries, factories, and warehouses have been converted to lofts — or replaced with condo towers. There are still a few of the original working class houses along side streets. They’re getting a makeover the size of Hudson Yards known as the Canary District.

Danforth Village: Astoria

And not just because they’re both Greek. Danforth Avenue is lined with family shops with adorable houses and yards on the blocks behind, even though the subway runs below it.

East York/Danforth: Bay Ridge

It’s an easy commute to downtown, but let’s be honest that no one who lives here is leaving the neighborhood. It’s a relatively affordable neighborhood and young families are making their home here.

Leslieville: South Slope

Leslieville is incredibly charming, but this low-density family neighborhood pulls down the shades and goes to bed early. Expect a lot of strollers.

If your social life revolves around brunch and ice cream, this is the neighborhood for you. Finding a place in Leslieville can be a feat, since there are so many single-family homes and very few apartments. The Queen car runs through the heart of the neighborhood, which is very picturesque on the weekends, but is a drag when you’re stuck in traffic during rush hour.

Harborfront: Long Island City

Kind of soulless, but kind of lovely. Clean streets, good transit, and all these new condos with central air. Oh, and the lake.

Regent Park: East Harlem

Regent Park and East Harlem are both areas with large amounts of public and affordable housing undergoing rapid gentrification. Both have access to fantastic green spaces and the promise of new subway access, maybe, one day. Yet, for all the talk of hipsterization, there’s an odd lack of places to sit down and eat.

Regent Park is a neighborhood of gleaming new high rises, with a few mid rises and townhouses thrown in. The area has several fantastic parks, a brand new rec center, and all the essentials (groceries, pharmacies, doctors) within blocks. There are shops and cafes along Parliment and Queen.

The major drawbacks are the constant construction and the lack of subway access. Most of the previous residents of Regent Park were displaced temporarily during construction while loads of new residents have moved in, so there’s a major shift going on. There’s no shortage of streetcars and busses.

Yonge/Dundas & Moss Park: Port Authority

Or, more accurately, Hell’s Kitchen & the Bowery in the 90s. If you weren’t around NYC in the 90s then take a walk around the Port Authority Bus Terminal now. You’ll get a pretty good idea of what the Bowery looked like 20 years ago with lots of homelessness, low income housing, and a few trendy spots thrown in for good measure. It’s also a super convenient location close to transportation and short walks to “hipper” neighborhoods.

Toronto Islands: Not quite New York

It’s got all the charm of small beach towns, but it’s still commutable to downtown.

Algonquin Island: Jersey Shore

This part of the island reminds us a lot of Ocean Grove. It’s quaint and adorable with beach access and residential homes. It’s quiet in the winter and crazy during the summer.

Ward’s Island: Hamilton Beach

I’m not just saying this because of the airport proximity. Ward’s Island is oddly shabby and forgotten, considering it’s one of Toronto’s top tourist attractions. It feels like a very forgotten corner of the city that might just fall into the water at any moment.

St. James Town: Roosevelt Island without the tram

Both of these neighborhoods were the partially-realized dreams of urban planners in another era. No one is quite sure what to make of them, but they’re just so convenient, even while feeling out of the way. Roosevelt Island has a much better view, but the treetop views from St. James’ apartment towers is still pretty sweet.

This 1960s vision gets a bad rap, but if you have a soft spot for giant tower blocks and excellent public transit access, you’ll be rewarded with some very affordable housing options. It may feel like Bloor and Cabbagetown are a world away, but it’s actually just a few minutes walk. You also have everything you need (groceries, pharmacy, post office) on site and easy access to hiking and biking in the ravines.

St. Lawrence: Chelsea in 2001

Chelsea is hot now, but that’s a fairly recent phenomena. They both have markets as their namesake, great old warehouse buildings converted into lofts and hip offices, and lots of high end furniture stores. They also both have an abundance of low income housing and a big highway cutting them off from the waterfront.

Life in St. Lawrence is incredibly convenient. It’s a short walk to everything: Union Station, Eaton Center, Queen West, the Distillery, the waterfront, even Billy Bishop Airport. It’s also a neighborhood where you can buy reindeer steaks and drink fancy cocktails at a sidewalk cafe. It may not be a cool place to live, but it has all the charm and history that comes with being Toronto’s original neighborhood.

Gay Village: Greenwich Village if it were in LIC

It’s mandatory to say Greenwich Village, but the Gay Village lacks the character and charm.

North of Bloor

The tourist maps suggest the city ends at Bloor, but it’s only getting started.

Annex: Greenwich Village, the west side

The other neighborhood so famously saved by Jane Jacobs.

Christie Pitts: Kensington

Kensington is an overlooked gem with cheap international food, cute family homes, and neighborhood shops, all with easy access to Prospect Park and the subway. Since this is the Canadian Kensington, it also has a spot for tobogganing.

Rosedale: Riverdale

Riverdale in the Bronx is sort of lovely. There are large estates that feel almost suburban, but are still in the middle of a major metropolitan area.

St. Clair: Clinton Hill

Clinton Hill with a little bit of Flatbush mixed in.

Yonge & Eg: Jersey City

Jersey City has a skyline of its own, but no one ever gives its due. Yonge & Eg feels more urban than downtown, but people act like it’s the suburbs.

If you’ve always dreamed of living in one of those self-sustaining buildings in Sim City, you can live the dream at Yonge & Eg. There’s a massive mall, movie theatre, office building, apartment building above the subway station. What more could you want?

Yorkville: Upper West Side

Full of designer shops and celebrity sightings. Used to be full of hippies. Not enough brunch places, but that’s all of Toronto.