A new species of the Caribbean genus Cyrtopholis Simon, 1892, Cyrtopholis montserrat sp. nov. is described from the United Kingdom Overseas Territory (UKOT) of Montserrat, based on both sexes. Cyrtopholis femoralis Pocock, 1903 is redescribed from the holotype male with the first figures of the genitalia of this Montserrat endemic spider presented. The endemic Saint Barthélemy species Cyrtopholis antillana Thorell, 1894 stat. rev. is revalidated from synonymy with Cyrtopholis bartholomaei (Latreille, 1832) and non-type specimens of both sexes are described and diagnosed. Cyrtopholis innocua (Ausserer, 1871), C. intermedia (Ausserer, 1875), C. ischnoculiformis (Franganillo, 1926), and C. obsoleta (Franganillo, 1935) are proposed as nomina dubia, and Cyrtopholis respinus Franganillo, 1935 is confirmed as a nomen nudum.