Japan’s compact city policy, a rational response to demographic decline, is built on a core assumption: improving accessibility in urban cores will attract population. This chapter challenges this foundational premise through a case study of Odawara City. Our analysis reveals a critical paradox: areas with the highest accessibility are, counterintuitively, experiencing the sharpest population decline. This trend highlights a critical misalignment between existing facility distribution and evolving demographic patterns, challenging the foundational objectives of the government’s Location Optimization Plan. Our analysis over the past 5 years reveals significant discrepancies between policy intent and reality. Despite approximately 80% of the population residing within a nominal 15-minute living sphere, overall accessibility to essential services is declining. Crucially, the anticipated accessibility improvements around major railway stations have failed to materialize, signaling an inability to effectively intensify core urban functions. Through a detailed examination of development patterns around key nodes, this research assesses the policy’s limited effectiveness and illuminates the divergent, often contradictory, development trajectories unfolding across the urban landscape.