Coal is a nonrenewable resource. Hence, it is important to improve the coal recovery ratio and ensure the stability of coal mines for sustainable development of mining cities. Partial extraction techniques, such as strip pillar mining or room-and-pillar mining, are efficient methods to extract coal. Pillar stress is a critical property for pillar design and for the assessment of mine stability after partial extraction. Current pillar stress calculation methods can sometimes overestimate the pillar stress and unnecessarily large coal pillars may be left underground, which leads to a waste of coal resources. In this paper, the size effects of mining activity on the maximum vertical pillar stress were investigated using numerical simulations. Both strip pillar mining and room-and-pillar mining were considered as possible mining scenarios at different mining depths. The results show that the maximum pillar stress of a mine is primarily controlled by four factors: the mine size to mining depth ratio, the mining width to pillar width ratio, the overburden elastic modulus, and the mining depth. The maximum pillar stress of a mine gradually increases to an ultimate value as the mine size increases. Simplified formulas and methodology have been derived for stress calculations under consideration of mine size effects and, therefore, can reduce the waste of coal resources from the overestimation of pillar stress.