Cultural heritage buildings are valued in contemporary societies as they reflect the lifestyles and creative achievements our predecessors. For this reason, many countries have introduced regulations to ensure conservation of their historic buildings for the future, permitting minimal changes only to their original structure and characteristics. The key question addressed in this study is: how best can we assess the current structural behavior of a historical building, in particular wooden structures which may have survived for several centuries despite the deleterious consequences of decay, ageing and earthquakes? This paper focuses on a structural behavior assessment under current conditions (i.e. before restoration) of the Velipasa Han Building, an impressive "caravanserai" or han (inn) building dating from the 19th century, in the central Anatolian region of Turkey. This assessment includes non-destructive tests to obtain the resistance of the timber structural elements and to determine the modal response of the building. In addition, a finite element model was developed, based on an on-site investigation and the proposed restoration project, and validated by consideration of in situ experimental measurements. The model also used a condition assessment of the building after proposed restoration. Through in situ inspection, experimental measurement and numerical investigation, the current structural behavior of the building was evaluated and, based on this, recommendations for intervention are presented in the study.