Flavan-3-ols intake is associated with numerous health benefits, but these are influenced by their conversion into smaller phenolic metabolites by the gut microbiota. Thus, the identification of bacteria that metabolize flavan-3-ols could lead to targeted interventions to enhance their benefits. To this end, we screened 47 Lactiplantibacillus plantarum strains for their ability to metabolize (+)-catechin, a flavan-3-ol. Then, we assessed these strains for their capacity to convert various flavan-3-ol structures. Out of the 47 isolates, 12 released 3-(3′,4′-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-propan-2-ol (a form of diphenylpropan-2-ol) from (+)-catechin. All strains metabolized (+)-catechin, (−)-epicatechin, (−)-epigallocatechin, but only a subset transformed (−)-gallocatechin. Among these simple flavan-3-ol structures, (−)-epicatechin was metabolized the most. A hierarchical cluster analysis identified two groups of flavan-3-ol-metabolizing strains categorized as having "high" and "low" production of diphenylpropan-2-ols. Notably, the strains that produced higher levels of diphenylpropan-2-ol from (+)-gallocatechin and (+)-catechin also performed better with a camu−camu extract, which was studied as a complex source of flavan-3-ols and predominantly contained these two flavan-3-ols. These results demonstrate the interstrain variability in L. plantarum metabolism, which may be useful for developing tailored formulations to enhance the production of flavan-3-ols bioactive metabolites.