The insurance market deliberately excludes the buildings’ envelope from their insurance policies, neglecting all the damage that can be caused by the degradation process or ageing of the materials. This stance is mainly due to the lack of knowledge in terms of risk and costs associated to the failure of these elements. Even though the building and its elements are the most valuable asset of any owner, most often homeowners do not adopt effective preventive measures to mitigate the deterioration and obsolescence of their assets. This study proposes an innovative methodology for the design of insurance policies for buildings’ envelopes, applied to natural stone facade claddings. The insurance product is defined based on deterministic and stochastic service life prediction models, established through the past degradation history of 142 natural stone claddings analyzed in service conditions in Portugal. Single-parameter (only analyzing the cladding’s age) and multiparameter (encompassing the relevant variables) models are applied in the calculation of the insurance premium. The expected claims are related with the performance of maintenance actions and established according to three degradation levels. The results obtained reveal that an increased knowledge about the insured cladding leads to a reduction of the risk margin and consequently, to a lower annual value of commercial premium paid by a household. This study proposes an innovative solution for tailoring the insurance products, in terms of the risk of failure of the buildings components, as well as the financial charges related with the maintenance of these elements, channeling the risks to the market.