Rural Australia has been experiencing dramatic agricultural restructuring. A major contributor to this in some areas is peri-urban and rural residential developments, and amenity/lifestyle developments, including those associated with the inflow of urban middle-class groups into rural areas. These processes are intertwined with neoliberal trends in agri-food governance, and have complex effects on farming. However, there is a lack of farm-level studies that explore how professional farmers have been interacting and co-existing with urban/suburban development while also undertaking agricultural intensification and innovation. This study aims to examine how residential and amenity/lifestyle developments have unfolded in the Illawarra region, New South Wales, and come to influence and interact with local dairy farmers who are also managing the consequences of industry restructuring particularly from 2000. Based on semi-structured interviews, this study shows that with their proximity to Sydney, Illawarra dairy farms are influenced by deregulated planning systems, large-scale residential development, amenity driven demand for rural land, and the amenity/lifestyle economy. These processes bring farmers commercial opportunities and drive farmers to form new social and economic relationships with land buyers and investors. However, it has been increasingly difficult for farmers to acquire land for farming locally. They are also subjected to the expectations and demands of new landholders, including in relation to farm externalities and animal welfare. Farmers have to transform their production systems to fit into this context. The above factors together generate a form of multifunctional rural space.