Parallax doesn't list Windows 8 as one of the supported systems, but both the Stamp and Propeller software install properly and appear to run properly under Windows 8. I've not had any problems with Parallax software.
I just installed Win8 (slow but straightforward) in my 2005 Compaq desktop and downloaded the PBasic editor. When I plugged in Parallax's USB/Serial adapter (#28030) it loaded the driver automatically. It was so fast that I think the driver came from Win8 without going online and searching for it. It works properly and I programmed a BS2 Homework board.
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Just to be safe I'm keeping my old HD intact!