SSH alone does not transfer files but it allows transferring a stream of data and running commands on the remote computer.
This means that you can use any utility which will transform your files into a stream of data pass the stream through SSH and on the other end do the reverse process - extract the files from the stream. Below is an example with
find /source/path -iname "*.ext" -print0 |
tar --null -cf- -T- |
ssh user@machine "tar -xf- -C /path/to/extract"
The command sequence can be on single line I added newlines for better readability. Probably only GNU tar has the
If you do not have the suitable tools on your Windows you can install for example Cygwin.