With the Open SSL 0.9.7c library, developers can write applications that take advantage of Secure Sockets Layer (SSL v2/v3), Transport Layer Security (TLS v1), and a full-strength general-purpose cryptography library. Security features such as data integrity, authenticity, and privacy can be implemented. To compile for Win32, Perl or compiling under Cygwin is required. Some of the encryption routines/algorithms are covered by patents.
MobaSSH is a free SSH server for Windows, compatible with any ssh client (OpenSSH client, Putty, ...).
MobaSSH comes with an easy to use installer and some useful GNU utilities for monitoring and managing a remote computer silently. It also allows you to transfer files securely with scp/sftp.
MobaSSH is packaged in a small single executable that registers as a Windows service so that it can be monitored like other normal Windows services.