Herringswell was recorded in Domesday as "Herningawella" or "Hyrningwella". It appears on John Speed's 1610 map as "Heringeſwell".
Sir William Gilstrap had the Red House built with the intention of it being a pub, but his head gamekeeper persuaded him against opening it on the grounds that it would "encourage poaching". An adjacent cottage was an offlicense called the Live & Let Live. More recently the Live & Let Live social & drinking club ran for a few years at the village hall, though that has since folded.
Herringswell Hall is a mock-Tudor house dating from 1901, which was built on the site of the original manor. In the early 1980s it attained some notoriety as the headquarters of the Bhagwan Shree Rajneesh sect. When they left, they were replaced by a Japanese Buddhist school, which lasted until 2001. The hall is now subdivided into flats.