Structural changes in agriculture and urbanisation affect land management regimes and local landscape functions. Studying the new functions of land is as relevant as the owners' land management decisions, the replacement of farming with different activities and land uses may impact not only the local landscape's functions but also, in the long run, its structure and the environment. Drawing on a detailed case study in Tuscany based on qualitative interviews with landowners and on the understanding of the socio-economic context, this article analyses landowners' attitudes towards land property and farming in relation to individual motives as well as to local and supra-local contexts. Five relational typologies of landowners are identified: pure farmers, amenity farmers, land developers, land-with-house owners and house-with-land owners. Diverse trends – such as particular farmers’ attitudes towards land development, or the emerging role of non-professional farmers in land management – are found to raise challenges related to rural land planning and management.