Population aging represents a significant trend in shaping contemporary urban areas, and research investigating various aspects of age-friendly cities and neighbourhoods has enjoyed increasing attention from urban scholars and practitioners. The neighbourhood transformations that have been taking place in socialist high-rise panel housing estates in the last 20years raise concerns as to how they are experienced by local elderly populations. Although a number of studies have addressed recent developments in high-rise panel estates in countries of Central and Eastern Europe (CEE), little is known about the self-perceived residential quality of elderly inhabitants. This paper investigates the neighbourhood satisfaction of the elderly living in housing estates in Prague, the Czech Republic. The focus of this study is on their perceptions of the opportunities and barriers presented by the changing residential environments in relation to their daily independence. The paper takes a time-comparative approach based on face-to-face interviews with elderly adults from three different study areas. The findings suggest that neighbourhood satisfaction is influenced, among other factors, by the “life stage” of the housing estate, by the individual circumstances of moving to the neighbourhood and by the time to adapt to the new environment. Although the elderly evaluate housing estates as convenient places to live, the risks related to demographic aging and the deterioration of local facilities must be taken seriously.