Rural buildings have undergone deep changes with the historical transition from traditional agriculture to industrial society. This paper discusses these trends in Italy, focusing on major changes in agriculture, design approach, and land-use planning, referring to some regional cases and relative building typologies. The analysis of the main historical treatises on the subject of farm building design allowed us to evaluate how the evolution of the technical approach influenced the architectural quality of rural buildings. This latter was traditionally based on a close relation between aesthetic values, functionality, and simplicity, broadly acknowledged only recently, as shown by the loss of landscape integration of farm buildings constructed in the last decades. By analysing the processes of reuse of historical buildings and construction of new farm buildings, we have found out different and time-evolving ways of referring to rural heritage and identity. In some cases, they have been considered important references, even through typological evolution aimed at combining traditional values with new needs and available techniques. In other cases, old farm buildings have been considered unsuitable things of the past, or rather have inspired new constructions based on an idealized and mystified concept of rurality. Since landscape integration of rural buildings plays a crucial role in the EU concept of agriculture, the choice of architectural quality postulates to be adopted for the design of new rural buildings is a key theme. Both consistency with pre-industrial tradition and typological discontinuity must necessarily consider consciously the relationships with historical buildings, whose important values have increasingly come to the fore over the last years. Once consistency with historical farm buildings is assumed as a design postulate, contemporary interpretation of traditional typologies through modern building techniques is a very challenging and topical field of study. Various degrees of consistency with traditional typologies are possible. Therefore, this approach calls for the development of analytic and metadesign methods aimed at decomposing rural building typologies into their essential physiognomical features, allowing designers to modulate them to meet ever-changing requirements.