It seems to me that these buildings are not modern and reflect architectural trends for their era. Modern buildings are built with maximum simplification. You won't find vintage style in a modern window catalog - https://thwindowsdoors.com/the-basics-of-how-to-install-replacement-vinyl-basement-windows/ Many Canadians will choose reliability and functionality over design. I myself chose according to this principle because I understand that local winters are much more severe (unlike the weather in New York)
Yes, these buildings are quite old. They have gone through a stage of restoration to preserve their orginal architecture. I don't know when these buildings were built. I guess it would be in the late 1800s or early 1900s.