As an economic engine of contemporary societies, the real estate market needs to be carefully analyzed in terms of both urban management and private or public investment. Information on this market’s behavior can facilitate the identification of turning points in societies’ economic history. Analysts should focus not only on conditioning variables and other important determinants of relevance to investment evaluations but also on the impacts of each variable or factor. Measuring these effects is a key activity in decision-making processes. Given real estate’s growing importance to sustainable economic growth, this study concentrates on creating a multicriteria model for evaluating large real estate investments. A constructivist, process-oriented approach was applied in group work sessions held with a panel of experts with experience in dealing with this issue. These specialists structured the problem of evaluating large real estate investments using value-focused thinking (VFT) and cognitive mapping. The best-worst method (BWM) was then applied to calculate trade-offs among decision criteria and calibrate the evaluation system. The results were presented to and validated by a representative of Instituto da Habitação e da Reabilitação Urbana (Institute for Housing and Urban Rehabilitation), who identified the advantages and limitations of the proposed model, and suggested possible improvements.