There's plenty of good, underpriced neighbourhoods, but it does mean looking outside the old City of Toronto. Regal Heights and Westmount in York (north of St. Clair between Bathurst and Caledonia), Cliffside in Scarborough, New Toronto/Alderwood in Etobicoke and much of East York are more affordable. East York and York have good transit connections. But they are becoming more popular.
Areas that are also quite affordable, but take, well, a higher tolerance level as they are not yet up-and-coming (and transit a longer ride), are Silverthorn and Mount Dennis (York), north Cliffside/Scarborough Junction, west Junction (beyond High Park Ave towards Jane, north of Annette), and the St. Clair East-Victoria Park-Dawes area. These are inter-war and post-war housing stocks, small houses, and not sought-after.
I don't really recommend buying into a barely-affordable shoebox condo. I think one can do well owning a condo as a primary residence long-term, but condo living could also end up being a trap of poor/incompetant management, bad neighbours, condo politics, heavy maintenance fees and difficulty selling.
Find a neighbourhood you like and rent a few years. No harm in that.