Medicinal plants are a valuable source of bioactive compounds with anticancer potential. Madhuca longifolia, traditionally used for inflammation and metabolic disorders, contains phytochemicals such as lupeol, gamma-tocopherol, stigmasterol, and betulin with reported cytotoxic and antioxidant properties. This study employed molecular docking to assess their interactions with Estrogen Receptor Alpha (ERα, PDB ID: 6URG), a key target in MCF-7 breast cancer cells. Docking was performed using CB-Dock/AutoDock Vina, and complexes were analyzed for binding affinity, cavity volume, and interaction profiles. Results showed that pocket C4 consistently offered the most favorable binding site for lupeol (-10.2 kcal/mol) and stigmasterol (-10.7 kcal/mol), supporting stable and specific interactions. Gamma-tocopherol bound moderately (-8.3 kcal/mol), whereas betulin exhibited weak binding (-3.2 kcal/mol) in the largest cavity (C1, 33,075 ų), highlighting that cavity size alone does not ensure effective binding. These findings identify lupeol and stigmasterol as promising leads for further in vitro and in vivo evaluation against MCF-7 breast cancer.