Mulitple Web Sites (IIS and Apache) and SSL

We have multiple Websites on one server (IIS) and one Apache Tomcat) also on the same server.

This has worked fine until now. We need secure pages on all the Websites. We can handle the multiple Websites on IIS by adding a different address on the NIC card and adding one of the address to each Web Site. Then all the Websites can share port 443.

But can we do the same with Apache Tomcat? I have been trying to find out how to set up Apache to work with multiple Web Sites using different IPs. I can see how to set up one Web Site and one SSL in the server.xml file. I assume I can't use the Domain Name to differentiate the Web Sites as I need to have SSL on all the sites. So based on what I have read, you need to have different IPs to differentiate the Sites since the Domain names will be encoded until after the SSL handshaking is done and the certificates have been chosen. Apache.org tells you how to set up SSL for one Site but I can't find anything on how to set up Multiple SSL Sites with different IPs.

Also, can we have the Apache Tomcat sharing 443 on the same Web Server as IIS? I wasn't sure about this as I assumed you can only have one application listening on each port. I am not sure if the IP:Port setup works inside an application only or also between Applications:

For example: if you could have more than one application listening on a port, does that mean that if I have SMTP running on a machine I could add another IP address to my NIC and have my application listen on Port 25 (what SMTP uses) but on the other IP Address. I assumed this was not the case - but I may be wrong here.

If there is a way around this without having to buy another server we would be thrilled.