I managed to build Python with OpenSSL 1.0.1e on Mac OS 10.8.4 using build-installer.py script during Europython sprint. I'll attach patches in few days, as I'll try to clean the code a bit. Currently the build works only for intel.

Here is an example output:
test-osx ~ ➤ uname -a
Darwin test-osx.local 12.4.0 Darwin Kernel Version 12.4.0: Wed May  1 17:57:12 PDT 2013; root:xnu-2050.24.15~1/RELEASE_X86_64 x86_64
test-osx ~ ➤ arch -i386 python3
Python 3.4.0a0 (default, Jul  7 2013, 17:12:34)
[GCC 4.2.1 Compatible Apple LLVM 4.2 (clang-425.0.28)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
>>> import sys
>>> sys.maxsize
2147483647
>>> import ssl
>>> ssl.OPENSSL_VERSION
'OpenSSL 1.0.1e 11 Feb 2013'
>>> ^D
test-osx ~ ➤ arch -x86_64 python3
Python 3.4.0a0 (default, Jul  7 2013, 17:12:35)
[GCC 4.2.1 Compatible Apple LLVM 4.2 (clang-425.0.28)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
>>> import sys
>>> sys.maxsize
9223372036854775807
>>> import ssl
>>> ssl.OPENSSL_VERSION
'OpenSSL 1.0.1e 11 Feb 2013'
>>> ^D
test-osx ~ ➤