Update again: Issue solved, I deleted and reimported the certificate to access the site and the problem went away, I don't understand what the problem was in the first place...
I have a strange issue. IE will not connect to a https site giving me the "Internet Explorer cannot display the webpage" but I can telnet to the host on port 443 just fine. I have two identical virtual machines in ESXi. The one running Windows Web Server 2008 R2 cannot connect to the site, the other can and as far as I can tell, the only difference is the version of OS. Any ideas ?