Literature and regulation on financial intermediaries consider real estate loans being credit risk mitigated exposures due to the role played by the collateral. The effectiveness of the mitigation stemming from the real estate collateral depends on the recovery value the intermediary can expect during the work-out period: the increasing of the default rate can determine the decrease in the recovery values due to the excess of real estates executions. Nonetheless, the relationship between defaults and recovery values can be influenced by specific factors, that is characteristics affecting the single exposure, and semi-specific factors, such as the type and the duration of the recovery procedure, the competent court and the geographic location; such factors can determine the default status and the recovery procedure occurring in different economic cycle phases. In Italy, real estate loans represent a relevant percentage of financial intermediariesí total assets and semi-specific factors appear to play a relevant role. The paper aims to study the confidence of the negative relationship between defaults and recovery values; moreover, the paper aims to verify the relevance of macroeconomic factors on both the borrowersí attitude to enter into default status and the real estate exposures recovery values during different economic cycle phases due to semi-specific factors influence. The empirical analysis is based on relevant long run aggregated data for the Italian market stratified by semi-specific factors.