Phenolic-linked health benefits of Bartlett and Starkrimson pear cultivars were investigated for the potential relevance in managing type 2 diabetes and hypertension using in vitro enzyme models. Further effects of fermented (0, 24, 48, and 72-h with Lactobacillus helveticus) pear juice on inhibition of Helicobacter pylori and proliferation of probiotic Bifidobacterium longum were also evaluated. High total phenolic content along with high 2,2 diphenyl-1-picrylhydrazyl-linked free radical scavenging antioxidant activities were observed in peel extracts of both cultivars. In vitro enzyme assays with peel and pulp extracts also indicated high inhibitory activity of α-glucosidase and α-amylase used as models for anti-hyperglycemia benefits. Only the aqueous pulp extract of Bartlett pear had angiotensin I-converting enzyme inhibitory activity used as model for anti-hypertension benefits. Fermented acidic pH samples of both cultivars showed H. pylori inhibition at 48 and 72h, while fermented sample of Starkrimson even showed inhibition at 24h. Both cultivar extracts did not inhibit growth of probiotic B. longum.