A roof surface temperature monitoring, utilizing remotely sensed thermal infrared image has been specifically proposed to explore evidential data for heating load in winter by cool roof. The remotely sensed thermal infrared image made it possible to identify area-wide patterns of changing trends of surface temperature according to rooftop color (white, black, blue, green) which cannot be acquired by traditional field sampling. The temperature difference of cool roof having a higher solar reflectance were ranged from $3^{circ}C$ up to $9^{circ}C$, compared to the general roofs. It is confirmed that there is a significant potential to the energy saving by introducing the cool roof in a Korean climate since up to $18.46^{circ}C$ difference in cool roof, compared to the general roofs in summer were already identified in Seoul, South Korea. It is anticipated that this research output could be used as a valuable reference in identifying heating load in winter by cool roof since an objective monitoring has been proposed based on the area-wide measured, fully quantitative performance of remotely sensed thermal infrared image.