No, there wasn't always a street there. It's a bit before my time, but I'm told there was a large "garden plot" there, not really a farm, but a good size plot of vegetables. Possibly owned by the house with the stone foundation.
Old Homer is right about Reilly. Reilly himself lived in a Victorian-style house on the 300 block of Park Street, since torn down to build 333 Park Studio's. Back when Park Street was politically powerful, one of the leading streets in the city. Many prominent people in politics and in community organizations and churches lived there. And it was a tight-knit community of houses with it's own little private school called the Gateway School. (now a condo building at 300 Park Street).
City Manager's used to be much more powerful than they are now. I believe he was the predecessor to the legendary Joseph Squillace, who was city manager from the 1960's right up into the 80's. Squillace lived in a house where Wellington Hall stands (Union & Clay), and he accumulated several houses, tore them down, and built the nursing home. His descendants still own and manage it.