What's the value of my S+W357 K frame 2.5" bought in 1999?

This question is very difficult to answer without knowing the model number and seeing pictures to verify condition.

Do you have the original box and documents?
 
Look around on this website and you will get some idea what they are selling for.

http://www.gunauction.com/

I just bought a 66-7 that was in really nice shape for $428 but see guns in excellant condition similar to it for $500 to $600.

Welcome to the Line.
 
I'll concur with marklyftogt; some people report that these sell for $400-$500 in their area, but where I live, that is a $550-$650 gun.
Selling that = big mistake
Although I ultimately can't tell you what to do with your stuff, I have to agree with this post on some level. Keep in mind that if you sell it, it may become VERY hard to replace. The more time elapses since S&W discontinued these, the higher the values are going to get, and fewer owners are going to be willing to part with theirs.
 
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