It is a rare species with a single erect, hairy leaf and one or two bright pink flowers and grows in only two seasonally wet locations, a few hundred metres apart.

[2][3][4][5] Caladenia winfieldii was first formally described in 2001 by Stephen Hopper and Andrew Phillip Brown from a specimen collected near Manjimup and the description was published in Nuytsia.

[3][4] The majestic spider orchid is only known from two populations a few hundred metres apart near Manjimup in the Jarrah Forest and Warren biogeographic regions where it grows under paperbark and Banksia trees in seasonally-wet places.

[2][3][4][5][6] Caladenia winfieldii is classified as "Threatened Flora (Declared Rare Flora — Extant)" by the Western Australian Government Department of Parks and Wildlife[6] and as "Endangered" (EN) under the Australian Government Environment Protection and Biodiversity Conservation Act 1999 (EPBC Act).

The main threats to the species are activities of feral pigs, inappropriate fire regimes, kangaroo grazing, hydrological changes and dieback caused by Phytophthora cinnamomi.