Considering how much they go for now, I got Vanark for $20, and Silent Bomber for less than that, both for the PS1. That was of course years ago before the hobby blew up. I also got Donkey Kong: Jungle Beat with the bongos and inFAMOUS 2 - Hero Edition for $20+, shipped, and both new. There are more, but those are the one's that come to mind at the moment.
As for consoles, the one that comes to mind is the Sony PlayStation SCPH-1001 that I got off eBay for $60; however, what's particular about it isn't exactly the console, but the games it came bundled with: Mega Man Legends 1 and 2, Mega Man X4, X5, and X6, and Mega Man 8. This was many years ago, the lady that was selling it didn't know what she had, and I remember finding her listing after sorting by new; I contacted her to ask how much she'd be willing to take for MML2, and, to my surprise, she replied with, "give me $60 and everything is yours". I didn't bother to take the conversation any further other than shooting her back with a succinct, "Sure!".
And on the topic of freebies, three or so years ago a was given a Wii that, not only was practically unused, had 2 SD cards filled with Virtual Console and WiiWare games.
