Oldest by release is my NES which I got recently as a sort of gift sort of "Well I'm not using it" from a family member.
Oldest in terms of owned by me the longest is my SNES which I got for Christmas when I was about 8-10 along with a CRT, I remember that Christmas quite fondly.
I don't find myself often going through the effort to play my retro consoles anymore with projects taking up a lot of my time. If I had the time, however, I'd happily use the consoles over emulating, which I do frequently.
Such a fucking vile thing to read while starting my morning