Climate change has reduced the comfort of community environments, and there is an urgent need to improve the health and well-being of low-income residents through design and technical measures. Therefore, this paper conducts research in the context of an ongoing social housing renovation project in Aosta, Italy, in a cold winter and hot summer Alpine environment. The study combined interviews, field measurements, and multiple software simulations to analyze the home of an older adult experiencing energy deprivation. The study found that the indoor acoustic environment quality meets the requirements of various sound-related standards. Still, the lighting and thermal environment must be designed to reduce glare and western sun exposure, and the air quality could improve. Residents’ demand for renovation is low technology, low cost, and high comfort. Therefore, suggestions for combining active and passive transformation measures and maximizing the use of climate and resources are proposed. The lighting and thermal environment are optimized based on the green wisdom of the Haylofts building of the Walser family in the Alps: increase ventilation and reduce indoor air age to improve air quality. Overall, a comprehensive assessment of extreme climatic conditions facilitates the quantitative and qualitative study and control of social housing environments, improves occupant comfort, and decarbonizes such social building stock.