Areas of Toronto that are appealing to affluent young professionals...

[King of Kensington]

...that their parents or older colleagues (say over 55) find just bizarre.

Maybe Parkdale or Kensington Market or the Junction or even a condo in the "new" Regent Park. I suspect very few say, older law firm partners would live e and remain very clustered in the blue-chip neighborhoods of the Bayview-Yonge-Bathurst corridor above Bloor, but you might have a handful of younger ones buying in these areas. It seems the younger generation has few qualms about living anywhere in the inner city.

My late grandparents probably would thought it was strange that I would choose to live south of Bloor!

 

[Admiral Beez]

This reminded me of my wife and I in the late 1990s. We'd just moved into our house in Cabbagetown, and we saw a walking tour with the guide exclaiming that this area is popular with young urban professionals. My wife and I looked at each other - she was a school secretary and I a sales manager at a confectionery company. We laughed that we hardly feel like professionals. Of course, that was when the area was affordable to the likes of us. Now, my entire block is lawyers.

 

[prosperegal]

...that their parents or older colleagues (say over 55) find just bizarre.

Maybe Parkdale or Kensington Market or the Junction or even a condo in the "new" Regent Park. I suspect very few say, older law firm partners would live e and remain very clustered in the blue-chip neighborhoods of the Bayview-Yonge-Bathurst corridor above Bloor, but you might have a handful of younger ones buying in these areas. It seems the younger generation has few qualms about living anywhere in the inner city.

My late grandparents probably would thought it was strange that I would choose to live south of Bloor!

Well, you DO have the Shangri-La, Trump (or whatever they're going to call it in the near future), et al south of Bloor, but many older people will consider Yorkville as "downtown." I don't really see the appeal to live in the financial district though. My parents don't quite "get" the appeal of, say, Ossington area restaurants and still trek up to Markham for Chinese food most of the time, despite living closer to Bloor. I find those restaurants a bore and don't really appeal to my generation. My rule: If your website sucks or is non-existent, I won't come.

 

[King of Kensington]

In the New York area, I'm sure there are a lot of older partners and execs living in Westchester, Connecticut or suburban New Jersey that find the appeal of much of Brooklyn or Hoboken to be bizarre.