If you allow me to think in Sterling instead of Dollars it's very easy, and I'll choose £500 as my cut off then it's easy, because all of my guitars except one have been below that price.
American Strat - £325. Still going strong almost 40 years later. Still my main gigging (electric) guitar. Still never heard anything as sweet as the neck pick-up on this one. Still way better than I am (hence never needed to upgrade).
Martin 00015 -£500. Local newspaper bargain. Smelled of smoke, but that aside so much mojo and the easiest playing finger-picking acoustic ever. Maybe too easy. It spoils me.
Tanglewood TW60 - £175. Ebay bargain. My most used guitar. I can't believe how good this is for £175 (including case, tuner, and stand! Inbuilt electronics, too). I use it at all my gigs and never fail to get complimented on the sound. It's so good it means I no longer have to go into guitar shops. Which is a shame.
Cheers
Derek