The profound transformations of traditional rural landscapes have heightened attention towards the recovery and valorisation of their buildings, often abandoned, to accommodate new landscape usage needs. This aligns with the principles of sustainable landscape management. However, knowledge of the rural real estate market remains largely unexplored. This research aims to define and examine the key features influencing the purchase of rural buildings, for shedding light on their market. The objective is to provide useful new insight to the property appraisers and real estate agents involved in the sale of traditional rural buildings, even if in conditions of degradation or abandonment and in traditional landscape contexts. Furthermore, these results could serve as a valuable resource for policymakers, enabling them to indirectly evaluate the impacts of urban and landscape policies on buyers’ preferences regarding key features of rural properties. The research focused on the ‘trulli’, traditional buildings located in the Valle d’Itria (Puglia, Southern Italy). First, a detailed market analysis was carried out with the support of local real estate experts, to survey the transactions of trulli and identify the features influencing their purchase. Second, the obtained dataset was analysed through network analysis, which enabled us to explore the role and importance assigned by buyers to the identified features. The results highlighted that the quality of the landscape where trulli are located changed the buyers’ viewpoint on the purchase features. In greater detail, price, area, potable water accessibility and level of maintenance of trulli were the most crucial features, particularly in high and medium landscape value zones, compatible with touristic and recreational activities. On the other hand, the annex agricultural surface covered a central function in low landscape value zone for possible agricultural uses.