This article presents three-dimensional printed and highly sensitive polydimethylsiloxane/multi-walled carbon nanotube sensors for compressive strain and pressure measurements. An electrically conductive polydimethylsiloxane/multi-walled carbon nanotube nanocomposite is developed to three-dimensional print compression sensors in a freestanding and layer-by-layer manner. The dispersion of multi-walled carbon nanotubes in polydimethylsiloxane allows the uncured nanocomposite to stand freely without any support throughout the printing process. The cross section of the compression sensors is examined under scanning electron microscope to identify the microstructure of nanocomposites, revealing good dispersion of multi-walled carbon nanotubes within the polydimethylsiloxane matrix. The sensor’s sensitivity was characterized under cyclic compression loading at various max strains, showing an especially high sensitivity at lower strains. The sensing capability of the three-dimensional printed nanocomposites shows minimum variation at various applied strain rates, indicating its versatile potential in a wide range of applications. Cyclic tests under compressive loading for over 8 h demonstrate that the long-term sensing performance is consistent. Finally, in situ micromechanical compressive tests under scanning electron microscope validated the sensor’s piezoresistive mechanism, showing the rearrangement, reorientation, and bending of the multi-walled carbon nanotubes under compressive loads, were the main reasons that lead to the piezoresistive sensing capabilities in the three-dimensional printed nanocomposites.