This article examines homeowners’ self‐reported values in the American Housing Survey and the Health and Retirement Study from the start of the recent housing price run‐ups through recent price declines. We compare ZIP‐Code‐level market‐based estimates of housing prices to those derived from homeowners’ self‐reported values. We show that there are systematic differences which vary with market conditions and the amount of equity owners hold in their homes. When prices have fallen, homeowners systematically state that their homes are worth more than market estimates suggest, and homeowners with little or no equity in their homes state values above the market estimates to a greater degree. Over time, homeowners appear to adjust their assessments to be more in line with past market trends, but only slowly. Our results suggest that underwater borrowers are likely to understate their losses and either may not be aware that their mortgages are underwater or underestimate the degree to which they are.