Habenaria sect. Macroceratitae from Brazil is revised, and seven species are recognized: H. bractescens, H. gourlieana, H. johannensis, H. longicauda, H. macronectar, H. nabucoi, and the newly described H. paulistana. A main feature of these species is the presence of long, separated, involute stigmatic processes. Habenaria bractescens, H. gourlieana, H. johannensis, and H. macronectar are distributed mainly from central and southeastern Brazil to southern Brazil and southern South America, whereas H. longicauda and H. nabucoi are distributed mainly from west central, southeastern and northeastern Brazil to northern South America. Habenaria paulistana is restricted to the state of São Paulo. Habenaria bradei, H. juergensii, and H. sartoroides are lecto-typified, and H. kleyi is neotypified. The identity of H. fastor is discussed and H. nabucoi is recognized as the valid name for this species. Seven other species previously placed in sect. Macroceratitae are sufficiently distinct and are removed from the section.