For filler composite systems used in strain sensor applications, piezoresistive effect, strain hysteresis, and repeatability are critical factors, which have to be clearly evaluated and understood. To investigate the effects of the aspect ratio and content of a multi-walled carbon nanotube (MWCNT) on the strain sensor properties of the composite, MWCNT/Polydimethylsiloxane (PDMS) composites with varying filler contents and aspect ratios were fabricated. In order to uniformly disperse MWCNTs on the polymer matrix, we used a three-roll milling method to generate high shear force for de-bundling MWCNTs. Mechanical and electrical properties of the MWCNT composites were evaluated for each case. In addition, through the cyclic stretching test, we optimized the strain-sensing properties of the MWCNT composites by considering their piezoresistive effects and strain hysteresis.