This paper describes the use of the Discounted Cash Flow techniques to the 10 proposals for the urban design International Competition ìUrban redevelopment of the hospital university of Santa Chiara, Piazza dei Miracoliî, advertised by the city of Pisa in 2007. The area is strategically placed in the heart of the old city centre of Pisa, immediately nearby the Dome square, listed as Unescoís world heritage site. The Free Discounted Cash Flow (FDCF) model applied to the case study is one of the evaluation methods of the investmentsí economic and financial sustainability broadly used by developers and investors, since it is an approach based on the concept of net operating incomes according to all the financing sources (equity and debts). The FDCF model has been applied to different operating options (selling/renting/managing) not considered in the competitionís proposals, in order to verify their economical and financial performances. Taking into consideration the outcomes obtained these analysis, the most profitable options have been selected considering the information given by the Internal rate of return and the Net present value.