Background Syphilis is known as the “great imitator” because of its polymorphic clinical manifestations. Condyloma lata are an uncommon mucocutaneous manifestation of secondary syphilis, generally localized in intertriginous areas, such as the genitals and anus. Extragenital localization of condyloma lata is considered unusual. Methods A case study of extra-genital condylomata is presented. To contextualise the case, a literature review of extra-genital condylomata lata was subsequently undertaken. The authors searched MEDLINE/PubMed, Scopus and Excerpta Medica/EMBASE English-language sources using the following keywords: “condyloma lata”, “condylomata lata”, and “condyloma latum”. Results Thirty-five papers (from 1940 to 2021) describing an extra-anogenital localization of condyloma lata were found and are summarized in Table 1. Patients were mainly males (82.1%), with a mean age of 31.9 years. Most of them showed other manifestations of secondary syphilis (53.9%). In a minority of cases (39.0%), concomitant anogenital condyloma lata were present, thus making the diagnosis easier. The toe web localization was the most documented (26.2%) followed by the oral cavity (23.8%). Conclusion In the presence of extra-genital condyloma lata, the differential diagnosis is not always clear, especially when no other muco-cutaneous lesions are observed. In the case of eroded or wet lesions involving any cutaneous fold, associated or not with other cutaneous manifestations, a sexual history should be obtained, and syphilis must be considered.