High-level density functional electronic structure calculations have been performed to analyze the effect of microsolvation with water on the electronic properties of ortho-aminobenzoic acid (o-Abz). The hydrogen-bonded interaction of o-Abz molecule with one upto three water molecules, o-Abz center dot center dot center dot(H2O)(n) (n = 1-3) have been considered in two different situations: once the solvent water molecules are placed close to the carboxyl (-COOH) group of o-Abz producing the o-Abz center dot center dot center dot(H2O)(n)(COOH) complexes and then the water molecules placed close to the amino (-NH2) group producing the o-Abz center dot center dot center dot(H2O)(n)(NH2) clusters. Variation of the vibrational spectra and energetics upon hydrogen-bond formation are analyzed and compared with available experimental data. The effect of cooperativity is also analyzed. Overall, the hydrogen-bonded o-Abz center dot center dot center dot(H2O)(n)(COOH) clusters are found to be more stable than the o-Abz center dot center dot center dot(H2O)(n)(NH2) clusters.