The conquests of Alexander III (“The Great”) transformed the economic as well as political landscape of ancient Greece and Persia. It produced a prolific coinage, part of which survives today. This paper uses a hedonic price modeling approach to analyze auction prices of the major coin type of Alexander the Great. The findings make it possible to identify the effects of specific coin characteristics on realized auction prices, sellers’ reservation prices (auction price estimates), discrepancies between realized and estimated prices, and the variability of auction prices around predicted prices, or auction price surprise. The findings reveal that similar considerations shape estimated and realized prices, but bidders consistently value positive coin characteristics more highly than do sellers. Realized auction prices, the difference between realized and estimated prices, and auction price surprise are increasing over time, particularly for the highest grade coins.