Experimental densities ρ and sound speeds u at (293.15, 298.15, 303.15, 308.15, 313.15, and 318.15) K and refractive indices nD at 298.15 K are reported for the 1-propanol + cyclohexane, 1-propanol + cyclohexene, and 1-propanol + cyclohexanone binary mixtures covering the entire composition ranges and under atmospheric pressure. The excess molar volumes, isentropic compressibility deviations, and refractive index deviations ΔnD were derived from the experimental data. Redlich–Kister polynomial was the mathematical model of choice to correlate the derived properties of the studied mixtures. In each case, the Redlich–Kister polynomial with an optimal number of parameters provided a statistically significant mathematical representation of the derived properties with standard deviations compared to the estimated expanded uncertainties of corresponding properties. Furthermore, the Perturbed Chain Statistical Associating Fluid Theory (PC-SAFT) was used to correctly model the density of pure fluids and mixtures, whereas the coupling of PC-SAFT with Schaaff’s collision factor theory (SCFT) and Laplace mixing rules proved to be successful approaches for modeling the speed of sound and refractive index, respectively.