Herein, we report a novel photocatalytic strategy for the intermolecular cyclopropanation of olefins with brominating agents. This protocol not only overcomes steric hindrance but also enables the incorporation of fluorine atoms into the three-membered cyclopropane ring, concomitantly constructing two quaternary carbon centers. Notably, the developed strategy exhibits a broad substrate scope and an excellent functional group tolerance. Furthermore, its synthetic utility is exemplified by the successful late-stage cyclopropanation of structurally complex molecules and drug derivatives, highlighting its potential for practical applications in organic synthesis and medicinal chemistry.