Sorry, my bad jhorta. I wrongfully assumed *nix environment.
The dll bitness (32 vs 64-bit) has to match the bitness of your executable.
The easiest would be for all (openssl might be accompanied with cryptolibs) the libraries to placed next to your executable.
for a system-wide installation of the openssl-libraries I do not have a clear answer for you as I am not a windows user (anymore). The locations are at first sight illogical e.g. 32-bit dll's inside a 64-bit named folder.
EDIT:for the system-wide locations on window, see
this post from Thaddy (but the whole thread might perhaps be of interest)