I wanted to let people know that I picked up Ryan Coyner's Python freetype2 bindings and pushed them forward quite a bit. It doesn't have complete coverage of freetype2 yet, but the main functionality is accessible and functional.
The binding is written in pure Python with ctypes and so has no dependencies. In order to enable people to work directly from the freetype2 documentation, it doesn't try to make the interface particularly Pythonic. As a result, you'll need to know something about ctypes to use it effectively.
I haven't yet verified it on Windows but that should come along fairly soon.
The freetype tutorials have been ported and are included in the test/ directory.
Leo