If you don't want to build OpenSSL from source and want an easy way of upgrading to the latest version of OpenSSL, I'd suggest taking the MacPorts route.
Download the correct .dmg file from http://www.macports.org/install.php.
Open it and run the installer.
In the terminal, type:
$ sudo port sync; sudo port selfupdate; sudo port install openssl
Older versions OpenSSL may require installing newer zlib, and zlib in it's turn may require installing XCode 3.1.4:
Here is the link to get XCode 3.1.4 somewhere at bottom of the page:
http://connect.apple.com/cgi-bin/WebObjects/MemberSite.woa/wo/5.1.17.2.1.3.3.1.0.1.1.0.3.1.3.3.1
http://matthew.mceachen.us/blog/download-xcode-3-1-4-for-leopard-716.html
To build OpenSSL this link may be helpful (not tested):
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