This paper examines some aspects of creating sustainable urban quarters that are compatible with their context; Is aimed to demonstrate that definitions of sustainable urban form, agreed for a sensitive context, are a valuable tool for a good urban design. Consequently, sustainable urban form that can affect energy use can be shaped according to various local idiosyncrasies, to micro-climate parameters and to a clear aspect of development form. By this point a development framework or masterplan has to outline principles on ecological planning and design. The paper shows some proposed urban schemes for the development of ecological quarters within selected former military areas. Such areas are located in the eastern and the western boundary of the city of Florence. The army barracks, currently act as a impermeable barrier between the urban and rural environment, but they are identified as great opportunities for the city’s future urban transformation.