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In the last 20 years, high-rise housing has become the main way in which real estate development has been expressed in Chile. The pre-existing urban deregulation in terms of housing policy and the flexibility in regulatory guidelines triggered an explosive process of verticalization and a negative perception in the population, who have rejected high-rise projects, exerting pressure on municipalities to modify their regulatory plans (PRC) and restrict verticalization. This article is based on the study of 10 municipalities with the highest residential vertical housing development in the main Chilean metropolitan areas (Santiago, Valparaíso, and Concepción) from 2002 to 2021. The methodology is based on characterizing the role of municipal urban planning and accessibility to public transport in residential verticalization. The results show two trends related to territorial planning instruments linked to access to public transport. The discussion focuses on two findings: 1. Intensification of residential verticalization linked to changes to the PRC, 2. Intensification of residential verticalization unrelated to modifications to the PRC. It is found that in the planning processes, processes of vertical intensity are triggered that are averse to what has been proposed.