Energy-efficient retrofits embrace enhancement of the building envelope through climate control strategies, employment of building-integrated renewable energy technologies, and insulation for a sustainable city. Building envelope improvements with insulation is a common approach, yet decision-making plays an important role in determining the most appropriate envelope retrofit strategy. In this paper, the main objective is to evaluate different retrofit strategies (RS) through a calibrated simulation approach. Based on an energy performance audit and monitoring, an existing building is evaluated on performance levels and improvement potentials with basic energy conservation measures. The considered building is experimentally monitored for a full year, and monitoring data are used in calibrating the simulation model. The validation of the base model is done by comparing the simulation analysis with the experimental investigation, and good agreement is found. Three different retrofit strategies based on Intervention of minor (RS1), Moderate (RS2), and Major (RS3) are analyzed and juxtaposed with the base model to identify the optimal strategy of minimizing energy consumption. The result shows that total energy intensity in terms of the percentage reduction index is about 16.7% for RS1, 19.87 for RS2, and 24.12% for RS3. Hence, RS3 is considered the optimal retrofit strategy and is further simulated for a reduction in carbon dioxide (CO2) emissions and payback investigation. It was found that the annual reduction in CO2 emissions of the building was 18.56%, and the payback period for the investment was 10.6 years.