<em>Resident and resident assistants</em><strong> </strong><em>are designations for colonial officials assigned to assist the Governor-general of the Dutch East Indies in the administrative area of the residency level. This research aims to trace the existence of Dutch colonial heritage buildings in the administrative area of the Madiun Residency, now termed Madiun Raya, consisting of Madiun, Ponorogo, Pacitan, Ngawi, and Magetan. This research is obtained through a unit analysis research with the main subject being Dutch colonial buildings and a historical approach. The stages are heuristics (gathering sources), source criticism, interpretation, and historical writing. This research results in four findings in the form of official residences for Residents and Resident Assistants who have ruled Madiun Raya from 1830 to 1942, including the official residence of Madiun Resident, official residence of Ponorogo Resident Assistant, official residence of Pacitan Resident Assistant, and official residence of Ngawi Resident Assistant. Then, it explains the transition function of the four buildings in the present.</em>