Windows in buildings primarily enhance occupants’ views of the outdoor surroundings, improve ventilation, mitigate pollution sources, add visual appeal, and provide natural light. They are crucial for maintaining indoor thermal conditions and minimizing overall energy consumption. The study aims to assess the connections between the frequency of window openings and closings and the indoor environmental conditions. This research examines how these conditions impact window operation across various seasons. The case study is in Buckinghamshire, England, and features innovative buildings constructed with structural insulated panels. The research examines three residences within this development, utilizing HOBO sensors, including state loggers, to monitor indoor conditions and track window operations at intervals during summer and winter. The results indicate that windows in lower and upper floor spaces facing main streets were closed over 50% of the time due to noise pollution, safety concerns, and other factors, with limited openings for only a few hours each day. In contrast, windows in inner street locations remained open for more than half of the monitoring period. Patterns were observed between higher temperatures and window status throughout the buildings. During winter, windows were kept closed to improve indoor conditions and reduce heat loss. This study demonstrates that indoor environmental conditions have a significant influence on window operations. Although the preferred temperatures for residents to open windows varied, this research provides valuable insights into the temperature range occupants prefer for opening and closing windows. These findings could significantly inform future studies on smart window regulations and the implementation of intelligent controls for indoor environmental conditions in buildings.