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Science fiction writers have been dreaming of homes that can understand our preferences, assist our daily chores and teach us to be healthier, more sustainable and more knowledgeable. While we are still far from achieving this dream, the recent development of mobile devices, wearable interfaces, smart home appliances, and machine learning offer unprecedented opportunities for homes to better understand our goals, preferences and contexts, as well as to facilitate our everyday tasks and decision making. These recent advancement open a new possibility to create homes beyond simple automation: they enable creation of homes to coach us to achieve our better selves. That is, homes that are not just smart, but wise as well. However, to develop a wise home, there are still two key questions: How can a wise home coach its occupants while considering their different goals and needs? How can a home integrates emerging sensors, devices and interfaces to better understand their goals, preferences and contexts in order to support coaching? To answer these two questions, in this dissertation I use residential heating and cooling control as a lens to advance the development of wiser homes. Based on the three studies conducted, this thesis provides three contributions. First, I show that we can integrate a diverse class of emerging devices, including mobile phones, smartwatches, in-home sensors and home appliances to capture important user contexts, such as individual preferences for thermal comfort. The integration of these emerging devices enables a home to better coach its occupants and potentially better support automation. Secondly, I show that mixed-initiative interaction is an effective approach in the design of a wise home, and further propose four design strategies to support mixed-initiative homes, namely, lightweight dialogue, proactive coaching, guided experimentation and mutual-learning. Finally, I demonstrate a novel system that integrates the above-mentioned strategies to support the development of wise homes, facilitating home occupants to identify actions to achieve a better balance between their comfort and savings goals.