This could be something that you bought for a higher price than what most people would guess based on the item, or it could be something you bought for a normal price that has gained significant value as time has gone on.
What made me think of this question is a LEGO minifigure I got with my “The Hobbit: An Unexpected Journey” disc. It is Bilbo Baggins in a blue coat that was apparently only sold in that movie box only at Target stores. Even considering the exclusivity, I would have guessed maybe $10-20 for such a tiny piece of plastic, but there are sold listings on eBay from $80 to $225. I could possibly even get towards the higher end of that number since I still have everything in the original box in good condition. It’s not worth a ton compared to some other items people may own, but I think most people would not expect nearly that amount.
I’ve sat in one. It’s a nice chair, but… well let’s just say office chairs are very subject to diminishing returns. I’d definitely buy one for $20 though.
This one’s 20 years old, and it’s been used heavily. It’s help up really well.