A metabolic feature of lactic acid bacteria (LAB) is the production of exopolysaccharides (EPSs), which have technological and functional properties of interest to the food sector. The present study focused on the characterization of the Weissella cibaria strain C43-11, a high EPS producer in the presence of sucrose, in comparison with a low-producing strain (C2-32), and on possible genetic regulatory elements responsible for the modulation of dextransucrase (dsr) genes expression. NMR analysis of the polymeric material produced by the C43-11 strain indicated the presence of dextran consisting mainly of a linear scaffold formed by α-(1–6) glycosidic linkages and a smaller amounts of branches derived from α-(1–2), α-(1–3), and α-(1–4) linkages. Molecular analysis of the dsr genes and the putative transcriptional promoters of the two strains showed differences in their regulatory regions. Such variations may have a role in the modulation of dsr expression levels in the presence of sucrose. The strong upregulation of the dsr gene in the C43-11 strain resulted in a high accumulation of EPS. This is the first report showing differences in the regulatory elements of the dsr gene in W. cibaria and indicates a new perspective of investigation to identify the regulatory mechanism of EPS production.