The Brown Vine Snake, Oxybelis aeneus, is considered a single species despite the fact its distribution covers an estimated 10% of the Earth’s land surface, inhabiting a variety of ecosystems throughout North, Central, and South America and is distributed across numerous biogeographic barriers. Here we assemble a multilocus molecular dataset (i.e. cyt b, ND4, cmos, PRLR) derived from Middle American populations to examine for the first time the evolutionary history of Oxybelis and test for evidence of cryptic lineages using Bayesian and maximum likelihood criteria. Our divergence time estimates suggest that Oxybelis diverged from its sister genus, Leptophis, approximately 20.5 million years ago (Ma) during the lower-Miocene. Additionally, our phylogenetic and species delimitation results suggest O. aeneus is likely a complex of species showing relatively deep species-level divergences initiated during the Pliocene. Finally, ancestral area reconstructions suggest a Central American origin and subsequent expansion into North and South America.