Two triazine‐cored BODIPY trimers (Compounds 6 and 12) were synthesized and well characterized using 1H NMR, 13C NMR, 11B NMR, 19F NMR, FT‐IR, and high‐resolution mass spectral analysis. The photophysical, computational, and in vitro anticancer studies of the synthesized compounds were comprehensively evaluated along with previously reported phenylene‐BODIPY trimer (Compound 1). The photophysical studies indicated that the triazine‐cored BODIPY trimers exhibited a slight bathochromic shift compared to the phenylene‐cored trimer. Density functional theory (DFT) calculations suggest that the order of stability of the BODIPY trimers was 1 > 6 > 12. The anticancer efficacy of the BODIPY trimers was investigated against human breast adenocarcinomas cell line MDA‐MB‐231 and mouse embryo fibroblast cell line NIH/3T3 through in vitro cytotoxicity assay. All the BODIPY trimers exhibited elevated cytotoxicity towards cancer cells while displaying lesser cytotoxicity towards normal cells. Compound 6 showed the highest cell death potential with an IC50 value of 27.02 μM, which is twice higher than that of the chemotherapeutic drug cisplatin. The triazine‐cored BODIPY trimers demonstrated superior cytotoxicity against cancer cells in comparison to their phenylene‐cored counterparts. The enhanced cytotoxicity of the triazine‐cored trimers suggests that the triazine core plays a crucial role in enhancing their therapeutic efficacy. This result underscores the potential of triazine‐cored BODIPY trimers as promising anticancer agents.