From the documentation:
'$'Matches the end of the string or just before the newline at the end of the string
Try \Z instead.
Also, any time you find yourself writing a regular expression that starts with ^ or \A and ends with $ or \Z, if your intent is to only match the entire string, you should probably use re.fullmatch() instead of re.search() (and omit the boundary markers from the regex). Or if you're using a version of Python that's too old to have re.fullmatch(), (you really need to upgrade but) you can use re.match() and omit the beginning-of-string boundary marker.