The research agreement between the University of Bologna and the Municipality of Castelfranco concerns the identification and assessment of the environmental and spatial sustainability of the new Urban General Plan the city is going to develop in compliant with the new regional urban planning law. Starting from an in depth analysis of the urban fabrics and building characteristics to get information about possible deficiencies in terms of public facilities and equipment and building performances, the assessment aims at defining sustainability conditions and targets for ensuring a sustainable and deep regeneration of the city by comparing possible alternatives.