The University of Connecticut Map and Geographic Information Center (also known as UConn MAGIC) provides this aerial imagery from 1934, which can be compared to a modern map. The image below shows the South Norwalk/Roton Hill area, but I can't seem to link to that placement directly. Instead, you'll have to navigate from the map's home position in Hartford.
Original: https://arcg.is/0auzuL1
These images were taken in 1934, shortly before a boom in housing development in the Roton Hill area in the 1930s and 1940s. You can see how much of this area was still wilderness.
In these images you can see the Ira Ford Hoyt property, before Brien McMahon High School was build over it.
You can also see the ponds along Keeler's Brook. There are still wetlands along that path, but I think we've significantly dried out that area.