Greek cities hold important urban issues related to social injustice; lack of open spaces, pedestrian facilities, parks and greenery, access to public amenities, etc. In view of these, we investigated residents’ preferences and choices regarding their walking activities in the urban environment of Thessaloniki, Greece. In specific, we applied research with questionnaires to the residents of the municipality of Ampelokipoi-Menemeni. The research applied the Contingent Valuation Method to investigate residents’ willingness to pay (WTP) for the improvement of the existing infrastructure of public space in view of making walking and the use of local metro stations more attractive. A methodological framework was developed, including Explanatory Factor Analysis and Structural Equation Modelling, along with statistical analysis of the results. The lack of pedestrian facilities and the long walking distances are two main reasons discouraging the use of the metro. CVM application showed that almost half of the residents would be willing to contribute an amount of money for the improvement of pedestrian infrastructure. The main reasons for this were to make the use of the metro more attractive, which would also improve their living conditions and would contribute to a better quality of life. Income restrictions proved highly important to a negative WTP.