The Sustainable Development Goals (SDGs) of the United Nations state that cities and human settlements need to be more inclusive, safe and resilient. In Europe cities have experienced dramatic physical, social and economic changes during the last decades while historic centres of European cities, among the most important assets of the European cultural heritage, are living paradoxes. They are defined as “a collection of beauty, icon of well-being, model of sustainability, but abandoned”. This study investigates the changes in the urban landscape of Nicosia, a particular historical centre in the Mediterranean region (Cyprus). The city centre is characterised by exceptionally well-preserved Venetian fortifications. Due to political circumstances, the capital of Cyprus, Nicosia, is still divided and has been ruled by two different administrations for several decades. This study used optical multi-spectral satellite datasets processing, like the Landsat and the most recent Sentinel-2 products, to detect, identify and characterise significant morphological transformations within the walled city and around it. This paper’s central thesis promotes a more systematic use of earth observation products and derivatives in decision-making processes that regard planning, use and management of urban resources in Europe, especially in support of urban planning strategies of historic cities.