cleansweep does the logging and windows does track usage, however its difficult to tell. Cleansweep does claim to be able to remove old software, but it doesn't make it clear who determines if its old
the search tool allows you to search on a last accessed date range, so as long as its ntfs you could do a search that shows all the accessed .exe files then subtract the ones used in the last N months.
windows does track exe's though so i bet theres a way to pull it out, it uses it for optimizing the disk layout.