Venous leg ulcers (VLUs) are one of the most common complications in lower extremity wounds. To date, clinicians employ visual inspection of the wound site during its healing process by monitoring surface granulation and reduction in wound size across weeks of treatment. In this study, a handheld near-infrared optical scanner (NIROS) has been developed at the Optical Imaging Laboratory to differentiate healing from nonhealing VLUs based on differences in blood flow to the wound and its surroundings. Noncontact near-infrared (NIR) area imaging of 12 VLUs have been carried out at two podiatric clinics. Diffuse reflectance images of the wounds were used to quantify optical contrasts between the wound and its surroundings. The variability in imaging conditions, analysis, and operator dependency were assessed to determine the robustness of the imaging approach. Optical contrast obtained from diffuse reflectance images of VLUs were distinctly different for healing (positive contrast) and nonhealing (negative contrast) wounds, independent of the varying imaging and data analysis conditions. NIR imaging of wounds to differentiate healing from nonhealing VLUs using a noncontact wide-area imager has been demonstrated for the first time. The application of a portable handheld imager to assess the healing or nonhealing nature of VLUs during weekly clinical treatment is significant since physiological changes, as observed using NIROS, manifest before visual reduction in wound size during the healing process.