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In this study, prostate cancer-targeted, drug-loaded PEtOx nanogel was prepared by the combination of living/cationic ring-opening polymerization and alkyne-azide cycloaddition “click” chemistry. A fluorescence probe was also conjugated with nanogel to track drug delivery. Nanogel formation was confirmed by 1H-NMR and FT-IR spectroscopies while SEM and DLS analyses showed uniform spherical nanogels and the particle size of nanogels could be controlled at 100-250 nm with relatively narrow size distributions. The physical stability of nanogels has been examined at pH 7.4 and %1-5 fetal bovine serum and intravenously administered nanogel formulations could remain in the bloodstream without much physical change until they reach the target site. The biocompatibility of the nanogels was evaluated using MTT cytotoxicity assays. The results showed that cytotoxicity was dose-dependent and drug-loaded nanogels against cancer cells in vitro were much higher than that of the drug-free nanogel. The targeting efficiency was examined with peptide conjugated and peptide-free nanogel. Intracellular uptake of peptide 563 conjugated nanogel by tumor cells was 60-fold higher than that of nanogel without peptide. Our findings suggest that prepared nanogel exhibits great potential to be used in a variety of drug delivery applications due to non-toxic, and enhanced intracellular uptake into the tumor region.