Update: I revisited this block in July of 2023 (fifth photo).
The Greater Ville was built in stages, with early exurban houses built for agricultural uses, and then later houses were built as the city proper came out to the open fields. This photo was taken from New Ashland Place.
I find it fascinating how these tract homes are customized over the decades.
Sadly, there is a large amount of abandonment on this stretch of Ashland.