This is fairly odd behaviour of macOS, the same error can be seen from a bash session:

$ stat /dev/fd/3
stat: /dev/fd/3: stat: Bad file descriptor

The reason os.walk() works while the Path().is_file doesn't is that os.walk() explicitly guards against OSError exceptions raised by os.stat(). 

Looking at the documentation this could be seen as a bug in macOS, as the manual page for stat(2) doesn't mention EBADF as a valid error for this system call.  

I'm not sure at this point if we should add a workaround for this. An actual patch would be easy enough, "just" add EBADF to the list of ignored errno values in the implementation of is_file (and related method) in pathlib.py