Richard came from the Whitelegh family of Efford in Egg Buckland, and was a kinsman, perhaps father, of the John Whitelegh who sat in Parliament for Tavistock in 1380. In 1364, following a settlement on them both in jointure, he and his wife took possession of lands in Churchstow (near Kingsbridge), and it was there, in their manor-house at Newton, that they later had their own oratory, by virtue of licences granted by Bishop Brantingham of Exeter in 1379 and 1387.
In 1391 Whitelegh purchased lands in Buckland-in-the-Moor, situated on the river Dart to the north of Ashburton, and in West Buckland near Kingsbridge. It seems most likely that it was he rather than his son of the same name who was returned to the Parliament of 1394 for Totnes, for he had acquired property in that town three years previously. He is last recorded in July 1395 when he, his wife and their heir obtained a third licence allowing mass to be celebrated in their home.
