The Schiff base, 2-[(2,3-dihydro-1H-inden-4-ylimino)methyl]-5-nitrophenol coordinates to Mn(II), Cu(II), Zn(II), and Pd(II) ions through the phenolic O and imine N atoms. The complexes are characterized by physicochemical and spectroscopic methods. The metal complexes formed as [ML2]xH2O with exception of the Cu(II) complex which is anhydrous. Spectroscopic data corroborate the adoption of a four-coordinate, tetrahedral geometry for the Mn(II), and Zn(II) complexes, and a four-coordinate, square planar geometry for the Cu(II) and Pd(II) complexes. None is an electrolyte in DMSO. The in vitro anticancer activities of the metal free ligand, Cu(II), Zn(II), and Pd(II) complexes against MCF-7 (human breast adenocarcinoma) and HT-29 (colon carcinoma) cells reveal that the Pd(II) complex has the best cytotoxic activity against MCF-7 cells with an IC50 of 5.94 μM, which is within the same order of activity as cisplatin. Furthermore, the ligand and the Zn(II) complex exhibit broad-spectrum activity against two gram-positive bacteria, three gram-negative bacteria, and a fungus with inhibitory zones range of 10.0–20.0 and 10.0–17.0 mm, respectively.