Toronto is a city of neighbourhoods. Some are nice. Some are less so. And, let’s be frank, some are downright sketchy.

Now, some people would lump most of downtown Toronto into this category (I have one friend who looks down her nose at Leslieville, for goodness sake), but I think most city dwellers would argue that “urban” does not equal nasty.

What’s the difference? On a typical city street you’ll see litter, convenience stores, people smoking outside bars, squirrels and, in residential areas, little front gardens.

In a sketchy ‘hood? The litter includes needles and condoms, the stores are boarded up, people smoke outside homeless shelters, rats have scared off the squirrels and front yards are simply storage spaces for rusted bikes, paint cans and creepy, decaying stuffed animals.

In other words, nowhere you’d ever think of moving, right? But here’s the thing about Toronto: Many of the nicest neighbourhoods border some of the worst. Leaside is beside Flemingdon Park. Roncesvalles is flanked by the grittier part of Parkdale. The million-dollar homes of Cabbagetown butt against St. James Town and Regent Park.

Heck, even within some neighbourhoods you find a mix of good and bad. In Corktown, some of the city’s most charming streets end at methodone clinics and missions.

So when you’re searching for a new home, don’t write off an attractive property just because you don’t like the address. Talk to your Realtor and/or go see it for yourself. Are you a big guy with a black belt? You might be able to tolerate some young dudes hanging about after dark. Are you worried about the woman with five kids living in community housing? Put yourself in her shoes. Sometimes a shift in perspective changes things.

Because here’s the thing about sketchy neighbourhoods: Very often they clean up. Cute little shops move in. Families renovate affordable homes. Next thing you know there’s a Starbucks. Just look at Leslieville.

Would you rather buy when a two-bedroom house sells for $400,000 – or $800,000? I think we both know the answer.

Thoughts about this article? What would you consider the sketchy areas in Toronto and would you ever live near there? Weigh in at


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