Crossing over Koeln Avenue (the German spelling for Cologne, well, replacing oe for ö), we see something that is rare along Pennsylvania Avenue: a corner store. That is most likely since we are just one block off South Broadway, which is a solid row of commercial buildings (see here and here).
There is a combination of front door and side door configurations, which becomes much more common in the last decades of the Nineteenth Century.
The house on the right below most likely had a two story side porch, and also note the ornamentation around the front door.
Crossing Upton Street we are back to more Greek Revival and vernacular housing stock, with the cornice missing and covered with vinyl siding.
But then, wow, look at these two Italianate houses. These are some extremely early and very old examples of the style.
Note how soft the brick is on the one above and to the left below; the brick was fired at a lower temperature, so we can date it to an earlier year. I suspect it was one of the earliest examples of the style in Carondelet and even in the St. Louis area. The one on the right below looks just as old but the paint obscures easy examination of the brick.
Below, someone must have gotten sick of their Mansard roof.