Abstract: Climate change and urbanisation have a major effect on the management and protection of cultural heritage landscapes, such as polder landscapes, historical villages and their surroundings, or archaeological landscapes that cannot be protected as a single monument. This article focusses on historical estate landscapes, whose character is determined by country estates and their lands. Here climate adaptation is also a significant challenge while addressing the abundance and shortage of water and changes in vegetation due to temperature increase. At the same time, the pressure is increasing due to ongoing urbanisation and related recreational needs. Also, these heritage landscapes have to deal with spatial fragmentation due to urbanisation, changing ownership, change of function, etc. The complexity of these challenges needs a regional perspective or ‘helicopter view’ to understand the coherence and systemic relationships between the estates and find common ground in which stakeholders can work together. This article introduces a landscape-based regional design approach for understanding, planning, and designing heritage estate landscapes, using learning cases from the Province of Gelderland (The Netherlands) as an example. It elaborates a preservation-through-planning approach that takes spatial development with historical landscape structures as a basis and engages in a process with meaningful stakeholder engagement and visualisation/communication to invent spatial strategies and principles founded on co-creation and collaboration using design research and research through design as an essential means.