In the coming years, the Netherlands is expected to face various climate change-related challenges. Until 2030, the Dutch government has set the goal for the development of nearly a million dwellings (De Jonge, 2022), whereby 600,000 dwellings are being carried out in areas prone to flooding (Deltares, Bosch Slabbers, & Sweco, 2021; Groenemeijer & van der Lelij, 2021). In literature, work has been done regarding the current use of adaptation pathways, policies and their impact on decision-makers and practitioners (Restemeyer, van den Brink, & Woltjer, 2017; van Alphen, Haasnoot, & Diermanse, 2022; Yousefpour & Hanewinkel, 2016). However, limited efforts have been made regarding their practicality in the real estate sector. This research seeks to address the fundamental question, “who pays what, when?”. At its core, this research revolves around the influence of climate risks on the investment decision-making process in polder-area developments in the Netherlands and examines the research question: “In which way do water risks impact the investment decision-making process in polder-area development projects in the Netherlands?”. In this qualitative study, the urban area development projects Westergouwe (Gouda) and Gnephoek (Alphen aan den Rijn) are compared and analyzed. With the use of explorative interviews, and semi-structured in-depth interviews, the research strived to answer the research question. Afterward, an expert panel is held to bridge the gap to standard practice. This research found that the integration of adaptive measures into the investment decision-making process is currently insufficient. There is a need for clear policy, clear distribution of responsibilities and prioritization of water safety over financial considerations in the investment decision-making process. By navigating this complexity, driven by collaborative efforts, a holistic approach becomes imperative to forge a path toward a more resilient built environment.