This research deals with the issue of the recovery of the historic urban fabric with a view towards ecological transition, nowadays considered the preferable direction of sustainability for the reform of the house–city–landscape system. The massive incentives provided by the Italian government for sustainable building, in view of the post-pandemic economic recovery, risk being reduced to mere support for the real estate sector, which turns the financial transfer from the public into an increase in asset value for the private sector. Such an incentive system could contradict the original function of the city, which is to be the privileged place for social communication and the creation of the identity of settled communities. A process of property development that disregards the distribution of income favors the most valuable property, thus increasing the socioeconomic distance between centrality and marginality. The latter is a condition that often characterizes the parts of the historic city affected by extensive phenomena of physical and functional obsolescence of the built heritage, and it is less capable of attracting public funding. The increase of building decay and social filtering-down accelerates the loss and involution of neighborhood identities; the latter constitutes the psycho-social energy that helps preserve the physical, functional and anthropological integrity of the city, due to the differences that make its parts recognizable. This study, with reference to a neighborhood in the historic city of Syracuse (Italy), proposes a model of analysis, evaluation and planning of interventions on the buildings’ roofs, aimed at defining the best strategy for ecological–environmental regeneration. The model presented allows one to generate a multiplicity of alternative strategies that combine different uses of roofs: from the most sustainable green roofs, but that are less cost-effective from the identity and landscape point of view; to the most efficient photovoltaic roofs from the energy–environmental point of view; and up to the most cost-effective ones, the vertical extensions with an increase in building volume. The proposed tool is an inter-scalar multidimensional valuation model that connects the multiple eco-socio-systemic attitudes of individual buildings to the landscape, identity, energy–environmental and economic overall dimensions of the urban fabric and allows one to define and compare multiple alternative recovery hypotheses, evaluating their potential impacts on the built environment. The model allows the formation of 100 different strategies, which are internally coherent and differently satisfy the above four perspectives, and it provides the preferable ones for each of the five approaches practiced. The best strategy characterizes most green roofs, 427 out of 1075 building units, 277 blue roofs, 121 green–blue roofs and 46 grey roofs.
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