The conservation of perceived scenery of traditional extensive and diversified landscapes is a valuable aim for reaching sustainable rural development. Considering the financial budget assigned and the application rules of European Union agricultural policy (Common Agricultural Policy—CAP), the relationship between perceived landscape benefits and CAP first pillar payments is an interesting aspect to analyze. In this study, a cost-benefit analysis has been carried out in a rural area of Central Italy that represents typical Italian conditions of hilly territories. Greening payment, a mechanism aimed to boost public goods, including landscapes and their ecological functionality, was selected as a proxy for policy cost of preserving traditional extensive landscapes. The benefits of greening have been evaluated through the analysis of the people’s willingness to pay for the maintenance of extensive and diversified landscapes. The analysis conducted does not explicitly consider the full range of environmental benefits determined by greening, even if some interviewees may have perceived them in addition to the visual perception of the rural landscape. The present study can contribute to the debate on the agricultural policy post-2020, especially for a future definition of long-lasting and cost-effective sustainable interventions in hilly and extensive rural landscapes.