The thing with craigslist (IMPO) is something is only worth what people see the competition as.
Say you have a $5000 car, but then someone lists the exact same car, same condition for $2800. Then your car (in the eyes of the majority of craigslist users) is now only worth $2800.
Tool boxes seem take a really big hit from new price compared to other items. However I have noticed that Craftsman branded stuff seems to hold their value well. Value also depends heavily on condition, since you didn't post a picture of your actual box. We really don't know the condition of it. Also location is a factor.
On the other hand that is a "better" chest than the standard 6 drawer top box. With it being ball bearing and greater than 12" deep like so many.
I think you would have to ask yourself what the lowest you would let it go for, then list it for ~$40 more than that. That way if someone gives you full asking price, great. If they do talk you down the $40, you still get what you wanted out of it.
Personally I would definitely pay up to $100 if it is in working condition. $150 if it works and looks good (no rust). MAYBE $180 if it was in pristine condition. Sorry but the market is extremely competitive and I am rather "economically challenged" shall we say. There is no way I would pay near $250 or $300 for that. That is getting close to a new harbor freight 44" cost, which is a lot more useful and spacious.
Best of luck with your decision