For example, I have a listing in Islamorada, Florida that the current owner has owned for nearly 30 years. Naturally, they paid a considerably lower price than what they are asking for the property now. They also made improvements over the years, such as a new deck, new kitchen and new metal roof, among other things. It makes no difference what they paid in 1985 in today's market.
Even in the event of a short sale, what the current owner paid for the property has nothing to do with what current market conditions are. In a short sale, the current owner almost always paid more than what they are asking now, or perhaps they've even taken equity lines out against the property. What the seller owes and what the house will sell for and appraise for today are unrelated.
The better question to ask is "what are similar properties selling for now?". It's best to look harder at sold properties than actively listed properties when answering this question, since asking price is rarely the same as the eventual sales price of the property.
Have a property you're interested in buying? Call or email me and I'll be happy to provide information on similar sold listings here in the Florida Keys.