I searched the net but didn't found any application that wrap ssh connection with GUI interface so that non techie people can connect to unix/linux accounts and work with files , so it will looks like there familiar Microsoft windows directory structure . Please don’t answer with .. just use xserver and such must of our servers don’t have any GUI installed .
WinSCP comes to mind. Or Filezilla. And those are only the most common.
Does it have to be an ssh connection? WinSCP would work fine there.
If not, then you could also configure SAMBA and let the users access their directories through the default home share.