Urban Rehabilitation (UR) in the Autonomous Region of Madeira (ARM), an Outermost Region of the EU, has become a strategic priority, aiming to preserve architectural heritage, revitalize degraded urban areas, and promote sustainable development. Funchal, with its rich architectural legacy, exemplifies the need to adapt historic structures to modern standards of comfort, energy efficiency, and accessibility while maintaining cultural identity. UR efforts have been supported by public and private investment, positively impacting tourism, commerce, and residents’ quality of life. ARM benefits from financial incentives, designated Urban Rehabilitation Areas (URAs), and national programs like IFFRU2020, which facilitate redevelopment through coordinated public-private initiatives. Previous studies (Parts I–IV, CIRMARE2023, CIHEL2024) detail these mechanisms. This fifth article continues research begun in 2017, focusing on 2023–2024 data from four municipalities: Funchal, Ponta do Sol, Porto Santo, and Santana. Buildings were categorized as Rehabilitated Residential (EHR), Large Commercial/Service (GES), and Small Commercial/Service (PES), subdivided by air conditioning capacity. Data from AREAM and PATRIRAM provided insights into energy performance, with Energy Class ratings used to assess impact. A case study in Funchal—the rehabilitation of the former Seminário da Encarnação by Teixeira Duarte—illustrates a level 4 “fachadismo” intervention, transforming the historic site into a modern school for International Sharing Schools. Overall, UR interventions have increased, especially in the project phase. Funchal leads in EHR volume, and programs like IFRRU2020, PRID, and “Casa + Eficiente” have proven effective, with URAs serving as key territorial management tools.