Date fruits (Phoenix dactylifera L.) are rich in sugar and also contain a substantial amount of phenolic compounds. Therefore, date fruits can be used to produce an alternative sweetener, having lower glycemic index than sucrose. This study investigated the effects of extraction and evaporation methods on various properties of the syrups prepared from Barhi dates. Extraction of date juice with the aid of pectinase or cellulase significantly enhanced the production yield, total phenolic content, and antioxidant activities determined by Ferric Reducing Antioxidant Power and Oxygen Radical Absorbance Capacity assays. Syrups prepared without enzyme application had about 6–7 times higher apparent viscosity than those prepared from the enzyme-assisted extracted juices. Vacuum evaporation produced syrups with significantly lighter color and inferior antioxidant properties than open heating. Properties of date syrups prepared with or without enzyme-assisted extraction followed by open heat evaporation were not different. They had a glucose-to-fructose ratio close to 1:1, received good sensory acceptability scores of above 6 on a 9-point hedonic scale, contained a safe level (<40 mg/kg) of 5-hydroxymethyl-2-furfuraldehyde, and exhibited similar glass transition and melting temperatures; while a greater inhibition on α-amylase activity was observed in syrups obtained from enzyme-assisted extraction. The in vivo glycemic measurement revealed that the syrup prepared with the aid of Pectinex and open heating was classified as low glycemic index (GI = 55) and medium glycemic load (GL = 11). Thus, enzyme-assisted extraction of date juice using Pectinex could be used to produce a healthy natural sweetener from low quality date fruits.