The recycling of polymeric materials has received a steadily growing scientific and industrial interest due to the increase in demand and production of durable and lightweight plastic parts. Recycling of such materials is mostly based on thermomechanical processes that significantly affect the mechanical, as well as the overall physicochemical properties of polymers. The study at hand focuses on the recyclability of Fused Filament Fabrication (FFF) 3D printed Polypropylene (PP) for a certain number of recycling courses (six in total), and its effect on the mechanical properties of 3D printed parts. Namely, 3D printed specimens were fabricated from non-recycled and recycled PP material, and further experimentally tested regarding their mechanical properties in tension, flex-ion, impact, and microhardness. Comprehensive dynamic scanning calorimetry (DSC), thermo-gravimetric analysis (TGA), Raman spectroscopy, and morphological investigations by scanning electron microscopy (SEM) were performed for the different 3D printed PP samples. The overall results showed that there is an overall slight increase in the material’s mechanical properties, both in tension and in flexion mode, while the DSC characterization indicates an increase in the polymer crystallinity over the recycling course.