This study reports the experimental relative permittivity, refractive index, and density data for several polar binary systems containing a cyclic ketone (cyclopentanone) and a series of alkanols from C-2 to C-10 over the entire composition range at T = 298.15 and p = 101.3 kPa. Further study was performed on a polar-nonpolar system composed of cyclopentanone and cyclohexane at the mentioned temperature and pressure. The experimental data were analyzed with various approaches in a consistence framework and in terms of intermolecular interactions between the constituent molecules. The effective and corrective Kirkwood correlation factors were calculated, in order to investigate the H-bond structure formation in the mixtures. The intermolecular interactions were investigated through various excess parameters, namely, excess permittivity, excess refractive index, excess molar volumes, excess Helmholtz energies, and excess Kirkwood correlation factors.