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I'm not sure how well it works, but you could do this with Pulseaudio. There are two separate builds of Pulseaudio for Windows. In either case, I think you'd need to configure each of those to startup automatically and to open ports on the Windows firewall.

Once you have that setup, the Pulseaudio documentation should get you started to broadcast over the network. For simplicity, I'd configure the native protocol to connect to a hard-coded IP address. One of the downloads above mentions that RTP is not supported on Windows, and I'm guessing that mDNS/zeroconf won't work either.

Most Linux programs will automatically use Pulseaudio, but if not, just use the padsp wrapper.

Something you could try is running a pulseaudio server on Windows. You can download precompiled binaries here http://www.cendio.com/pulseaudio/ and do some audio forwarding. It should work in both directions. Google some guides for the forwarding.

Disclaimer I have never used pulseaudio on windows

I haven't done this personally, but I believe it is possible to run a pulseaudio server on windows. You can download the binaries from here. After you get that set up, you should be able run the audio from the ubuntu box to the pulseaudio server on the windows box.

https://www.freedesktop.org/wiki/Software/PulseAudio/Ports/Windows/Support/

Maybe network server works, seems multicast/RTP doesn't.

Also Cendio used to have 0.9 build and ThinLic client also has pulseaudio but I haven't used it: http://www.cendio.com/thinlinc/download

I contribute to an open source remote desktop project (X2Go) that uses SSH for encryption/authentication and session handling. It works very well; we use libssh in the client, and the OpenSSH daemon on the server. A commercial competitor (ThinLinc) uses SSH too.

I did a similar set up with XP and seamlessRDP which worked mostly ok. The trouble was some apps would leave terrible artifacts and sometimes have non-responsive menus. It could be that Windows7 has better Terminal Services.. but I did notice in the video some artifacting but maybe it was the screen cast. I found i could minimise problems but making sure the Linux desktop was not using and compiz like effects.

Still a nice demonstration all the same. Thanks