I agree that the repeated 'Python x.y.z: " in the listing is too much.  #21588 has a patch but I am not ready to push it or do the review and revision needed . So I propose to reduce the current prefix to the minimum needed to know what version F5 will run the file with, x.y with minimal dressing, and put it in the middle or at the end. Your example Windows listing would then look like

  *Python 2.7.7 Shell*
  demo.py (2.7) /Users/raymond/class/demo.py
  download.py (2.7) /Users/raymond/class/download.py
or
  *Python 2.7.7 Shell*
  demo.py - /Users/raymond/class/demo.py (2.7)
  download.py - /Users/raymond/class/download.py (2.7)
or
  *Python 2.7.7 Shell*
  demo.py - /Users/raymond/class/demo.py | 2.7
  download.py - /Users/raymond/class/download.py | 2.7

Which do you like best?  I am trying out the second one in my 3.4 installation, and will switch to the third later.