Note: The following is a guideline for carpenter's toolchest values that was written by Mike Tillson about 5 years ago. Prices of course are always subject to change over the years. However it is very helpful and believe others might as well:
Perhaps I can help you out with some relative toolchest values, although I must warn you that this may only confuse the situation more!! Anyway, a good basic plain) chest, 24x36" more or less, in good condition should be worth at least $100. This would presume that the insides are blank, as in totally empty. The value of these chests depends heavily on what the inside looks like. The outsides were intended to be low key, and take all the abuse. The inside, was meant to please the owner, both in appearance, and in advertising of skill level to potential customers. On the lowest level of chest, the carcase will usually be constructed of a simple butt joint. On the higher levels you get dovetails, or even an exotic finger joint. The next tier up would be a chest with only one or two trays inside, all simple/plain, or perhaps ust a bit of decoration or fancy woodwork on the exterior. Something like a nice raised panel would boost it up a bit. I would put this level at about $200-$250.
Next tier would be be 4 or more trays, nicely done (dovetailed, etc), out of a nice wood like mahogany, cherry or some such. $250-$350, Next tier would include all of the above, but would have some inlays, carved borders, or something really special like that. This would definitely be a cabinet makers chest, or something of that level of quality anyway. At this level, all the trays should be dovetailed, and should be of some better quality wood. About $500. After this, there are some truely exceptional chests, that area obviously very artistic, masterfully done etc, and those are true one-of-kind types and they will go for much more. I saw one at Bud Brown's auction last year, which had closed, lidded trays, without pulls, almost like a novelty box or something. It went for $1200, but it was definitely VERY special. All burl wood on the cover, and upper trays, and stuff like that.
And of course, like most tools, condition is a major piece of the pricing, so even a fancy box which is all torn up will go for less money. One good thing though, usually chest prices are highly negotiable, because there is no "dealer book of values" on them, and of course the biggest reason is still that beauty is in the eye of the beholder, and some chests just plain seem to jump out and impress you.