IMHO ....
Actually if you are running FreeBSD, the easiest way to do these kinds of updates is to synchronize your ports tree.
Here are some instructions on how to do that.
After that you simply do:
1. cd /usr/ports/security/openssh
2. make
3. make install
4. make clean
And you should be all set (assuming that your DSA/RSA and host keys were already configured).
Of course, if you have problems with compilation, you also may have to update your gcc which I believe is under /ports/lang (I am not 100% sure, but since you have 4.4, you should be fairly current on gcc).
One more thing to look for: old crypto files, they may be
lurking around under /usr/lib.
Good Luck! Of course, remember to come back and share with us your solutions