Although much knowledge and debates about residential satisfaction exist, there is little evidence regarding its fluid nature and its influencing factors. Therefore, we suggest an analytical framework to investigate the dynamics of residential satisfaction by using data from a unique long-term study. Many previous studies have generally examined residential satisfaction using cross-sectional data at one point in time. But long-term observations are indispensable for discovering changes and/or continuity over time. For our analysis we utilized data from a study that was carried out over four decades and involved ten questionnaires. The study looks at a large housing estate (LHE) in East Germany. Our results concerning satisfaction with the estate and the apartments show the continuously high impact of residential comfort and sound insulation, and the declining impact of apartment size. Beyond that, the results reflect the development of this estate and also exemplify the political turbulence that this housing segment faced in East Germany.