Historically, white flat roofs have been used in Israel due to the intense solar radiation and long, hot, rainless summers. However, red pitched roofs have also been frequently used for aesthetic reasons. It has been recently observed that red pitched roofs have been recolored white by homeowners. The goal of this study was to compare the life cycle assessments (LCAs) of white flat roofs versus red or white pitched roofs through their production (P), operational energy (OE), and maintenance to disposal (MtoD) stages. EnergyPlus software was used to evaluate the OE stage. The ReCiPe method was used to evaluate the environmental damages in all the stages. A two-stage nested ANOVA was used to determine the significant differences between the ReCiPe result of a white flat roof and the ReCiPe result of a red/white pitched roof. It was found that (i) selection of the best roof technology (flat or pitched) requires consideration of the LCA, including the P, OE, and MtoD stages; (ii) the white (flat and pitched) roof was the best technology, while the red pitched roof was the worst technology; and (iii) the combination of the ReCiPe endpoint hierarchical six methodological options method with two-stage nested hierarchical mixed ANOVA is the best approach for assessing the differences related to the LCAs of roof technologies.