Mine are:
Logitech X220 speakers - still haven't found anything short of a $150 pair of studio monitors that sound as good as these. I paid ~$30 in 2001 for them.
And you can actually still buy them, too (as evidenced by my link).
White Apple keyboard - circa ~2004. I actually prefer it to the newer aluminum ones (keys are too low profile for my taste).
Sanyo 27" CRT TV - bought with wedding shower money in early 2005 as our main "living room" TV because flat screens cost way too much! Since been relegated to the bedroom, but works great and has outlasted two other LCDs that replaced it (the third time we bought a plasma and it's been fantabulous).
I also have a Dell Optiplex GX620 (Pentium D, 3GB RAM) that was retired from the school where I teach as a TV PC (we don't have cable; all we really use it for is to stream those "web-only" shows that aren't on Hulu Plus - The Walking Dead and Burn Notice, anyone?). Currently running XP, but I'm thinking strongly about moving it to Ubuntu.
But my oldest piece of still-working tech is the circa 1995 Phillips-Magnavox VCR connected to my home theater setup. It's used about once a year lol, but serves as a very nice digital clock.