In this study, individual selected lactic acid bacteria strains Lactobacillus acidophilus (LA), L. delbrueckii subsp. lactis (LDL), and L. gasseri (LGA) were grown in Chingshey purple sweet potato (CPSP) substrate/media. CPSP is rich in anthocyanin, which possesses antioxidant activity and in vitro cell assay. The antioxidant ability and functional properties of the fermented milk were examined. High-performance liquid chromatographic (HPLC) method was used to analyze the free amino acid, organic acids, and anthocyanin content. Total phenolic compounds, scavenging effects of 1,1-diphenyl-2-picyl-hydrazyl (DPPH) radicals, and scavenging effects of superoxide anion radicals were determined to evaluate the antioxidant ability of the samples. The cell proliferation of the fermented PSP milk was evaluated by 3-(4,5-dimethyldiazol-2-yl)-2,5 diphenyl Tetrazolium Bromide (MTT) assay. The result indicated that the antioxidant ability of the fermented CPSP milk through LA, LDL, and LGA strains was significantly higher than CPSP. The main anthocyanins present in the samples are cyanidin and delphinidin. MTT assay has revealed that incubation with both PSP and fermented CPSP milk prevented the cell death of macrophage-like RAW264.7 cells. The potential health benefit of fermented PSP milk through LA, LDL, and LGA strains makes the further application of CPSP in health food highly worthwhile. (1) In our study, we have employed the γ-aminobutyric acid (GABA), organic acid contents, total phenol content, anthocyanins content, DPPH, oxygen radical absorbance capacity, superoxide dismutase activity assay, and cytotoxicity assay to assess the functional properties of fermented CPSP milk by different lactic acid bacteria. (2) Our results have revealed that the fermented CPSP milk samples possess high GABA concentrations, organic acid contents, anthocyanins contents, and antioxidant activity. This will provide potential opportunity to develop different functional food products from fermented CPSP milk. (3) The potential health benefit of fermented CPSP milk makes the further application of CPSP in health food highly worthwhile.