Can two applications listen to the same port?

The answer differs depending on what OS is being considered. In general though:

For TCP, no. You can only have one application listening on the same port at one time. Now if you had 2 network cards, you could have one application listen on the first IP and the second one on the second IP using the same port number.

For UDP (Multicasts), multiple applications can subscribe to the same port.

Edit: Since Linux Kernel 3.9 and later, support for multiple applications listening to the same port was added using the SO_REUSEPORT option. More information is available at this lwn.net article.

Yes (for TCP) you can have two programs listen on the same socket, if the programs are designed to do so. When the socket is created by the first program, make sure the SO_REUSEADDR option is set on the socket before you bind(). However, this may not be what you want. What this does is an incoming TCP connection will be directed to one of the programs, not both, so it does not duplicate the connection, it just allows two programs to service the incoming request. For example, web servers will have multiple processes all listening on port 80, and the O/S sends a new connection to the process that is ready to accept new connections.

SO_REUSEADDR

Allows other sockets to bind() to this port, unless there is an active listening socket bound to the port already. This enables you to get around those "Address already in use" error messages when you try to restart your server after a crash.

Yes.

1. Multiple listening TCP sockets, all bound to the same port, can co-exist, provided they are all bound to different local IP addresses. Clients can connect to whichever one they need to. This excludes 0.0.0.0 (INADDR_ANY).

2. Multiple accepted sockets can co-exist, all accepted from the same listening socket, all showing the same local port number as the listening socket.

3. Multiple UDP sockets all bound to the same port can all co-exist provided either the same condition as at (1) or they have all had the SO_REUSEADDR option set before binding.

4. TCP ports and UDP ports occupy different namespaces, so the use of a port for TCP does not preclude its use for UDP, and vice versa.

Reference: Stevens & Wright, TCP/IP Illustrated, Volume II.