In relation to other cities of comparable size, Toronto is unique in having extensive pre-war residential neighbourhoods close to the urban core. These are the sort of neighbourhoods that were emptied in many cities in the mid 20th century as the white middle class moved to the suburbs. I am not a historian, but my impression is that in Toronto these neighbourhoods were preserved by the influx of immigrant communities, such that you still see the Polish influence in Roncesvalle, the Portuguese/Brazilian influence in Little Portugal, Italians in Little Italy, etc. As these immigrant communities aged, and started moving to suburban ethnic enclaves like Woodbridge, a number of these areas entered into decline (much later than comparable neighbourhoods in other NA cities). For instance, my area of North High Park, South Junction, or whatever you want to call it, was in material decline in the 1990s but this was arrested by the very significant cultural shift (assisting in part by the commuter problem) that resulted in many young families wanting to stay in the City. Almost none of the young people I know (by which I mean under 40) look to move out of the City of Toronto (not old but amalgamated) if they work downtown. Increased home prices is a result. This is a GREAT thing for the City.
I worked for 5 years after a graduate degree in a well remunerated field before I bought a 1400 square foot home. I was into my 30s. Most of those years were in NYC, making US dollars when that meant something. That's the way it is. If kids out of school with undergrad degrees and no parental support could buy homes in my area, that would be a problem, because it would mean it was the 1990s all over again and my area would be in decline.
Moreover, if you're straight out of undergrad, unmarried and no kids (I'm guessing here), why do you want a house in High Park? I suspect it is due to the misconception that renting is throwing money away, while buying is getting you equity. Well let me tell you, if you don't have a decent downpayment you're paying more in interest than you would be paying in rent, and if you're buying a 100 year-old home in High Park (mine is 106) maintenance is a big portion as well.
I don't mean to diminish the challenges this housing market can impose on people, but my sympathies don't lie with a well-employed kid just out of school who can afford a $450,000 place. The fact that many well-off families are rejuvenating our inner city victorian and post-victorian housing stock, and sacrificing significant square footage to do so (compared to what they could get in the suburbs), is one of the best things happening in the city right now. The huge numbers of condos going up in the city are perfectly suited for the likes of denfromoakvillemilton.