Daniel_Williams

Amazing what I've dug up here; from no to dumpy to not-much to numerous at least seemingly-good suggestions. I love it! I used to think Montreal's South Shore and West Island were pretty charmless and blah suburbia too based on WHAT I'D SEEN, but with a focusing on people's suggestions, I found that there were some really charming areas in the mix.

I notice there's a Unionville GO "G" line train stop; is this within walking distance of the historic, charming parts?

kodi

Daniel, I've held my tongue, but Oakville and Burlington are definately not dumpy.

I haven't been to Unionville for a long time, but I'm quite sure it's not dumpy either.
Markham is also nice.

Enjoy your exploring.

mat54

I did think of the Beaches district as well as High Park and Bloor West Village which BAK recommends. Oakville is pleasant as mentioned, some interesting shops and restaurants although I believe most of these are grouped on the main street downtown rather than mixed in with the stately mansions. I thought of Unionville, also mentioned above - on the northeast outskirts of the city, historic homes, shops, restaurants (although rather touristy). Look at http://www.unionvilleinfo.com/ . A little farther, up beyond the northwest corner of the city - Kleinberg is a possibility - it's quite cute with a few cafes, restaurants and shops and a famous art gallery (The McMichael Collection of Canadian Art featuring many Group of Seven paintings, works by Aboriginal artists and others). Don't know how easy it is to get there by public transit though.
There are a number of interesting small historic towns farther still but within day-tripping distance of Toronto, although for these you would need a car (e.g. Niagara-on-the-Lake, Elora, Stratford and others).