I found that there was a bug with Tomcat 5 running on Windows server 2008 64 bit. It attempts to use IPv6 over the default IPv4.
To resolve it, open up the Server.xml file and search for "<Connector". The top Connector will have the port that you're trying to communicate through, in my case 8080. In between port="8080" maxHttpHeaderSize="8192" type address="0.0.0.0" (Line will look like
port="8080" address="0.0.0.0" maxHttpHeaderSize="8192").
http://www.coderanch.com/t/506818/Tomcat/Unable-connect-Tomcat-Static-IP