To achieve sustainable development, governments have increasingly turned to legislating new rights, restrictions and responsibilities over land. These laws are designed to control the community’s behaviour in relation to land. Examples include the creation of water rights and the reallocation of land to indigenous peoples. Whilst the new interests aim to improve land management, they significantly increase complexity. Much research has focused on untangling the web of laws and administrative processes. To date, the focus has been the top-down requirements of government: less attention has been afforded to the bottom-up requirements of individual parcels and citizens. This paper aims to provide this perspective by presenting the results of a mixed-methodology study of four land parcels: a dense inner urban property, a medium density property, an agricultural property (dairy), and an isolated rural/recreational property. For each property, both a quantitative and qualitative study was undertaken. Each property was visited in order to understand what type of land interests applied, how they affected the land and how they were managed on-ground. The studies provided a detailed insight into the effect of old and new land interests on individual parcels. The impact of their creation, modification and removal was assessed. The lack of integration between policy, legal and administrative systems was experienced first hand. Additionally, the applicability of interests to different places, people, times and activities also became apparent. It is concluded that the results obtained must be considered in any new model attempting to improve the management of property interests.