Bump.
1.
Temple Building. Not much more needs to be said, especially when one looks at what replaced it. Would have been the perfect complement to Old City Hall right now.
2.
General Post Office Building on Adelaide and Toronto streets. Grand post office building and a great terminating vista. Most expensive federal building in the country at the time. Especially bad considering what replaced it.
3.
Provincial Lunatic Asylum. Already discussed in this thread.
4.
Toronto University Armouries. Come on. Look at that and tell me University Avenue wouldn't look better with that building there. York County Court House is sterile and doesn't provide anything but coldness to the feel of the street. The Armouries on a grand avenue like University is just a perfect fit.
5.
Original Union Station. Beautiful old train station, especially including the later Front Street addition. I think it would have done wonders for Front Street and the city if they kept it and were able to convert it into the convention centre or at least a meeting hall (a la Ottawa), instead of what exists today.
6.
Toronto Board of Trade Building. Obviously a beautiful building, and the perfect complement to the HHoF across Yonge, and the Gooderham Building behind it along Front.
7.
Toronto Mechanics Institute. Adelaide and Church would have been great if this was still there. First home of the Toronto Public Library as well.
8.
Old Toronto Star Building. I was debating whether or not to include this because it was replaced by something that has an even bigger impact on the city, First Canadian Place. However, my love of Art Deco and it being what inspired Superman's Daily Planet makes me include it.
9.
Old Bata Shoe Head Office. Not in a prominent location and not "beautiful and old", but it was a great example of a standalone modernist building that this city will regret ridding themselves of in the coming decades. At least it's being replaced by something (the Aga Khan Museum and Ismaili Centre), as opposed to a parking lot, cheap condo or nothing.
10.
St. Lawrence District. This one's cheating a little, but imagine if this was all kept. I love Berczy Park, but keeping all these buildings would have given Toronto a truly beautiful and all-encompassing "old town" like Montreal and Boston.
There's a bunch I could have included but didn't have the space for it. Toronto has been really terrible with preserving its history.