The story of the charity begins with its foundation by William Dalby in 1399, by virtue of a Licence granted by King Richard II. The original intention was that the hospital should have two chaplains, and should provide accommodation for twelve poor men.
The property was confiscated during the Abolition of Chantries actions of the 16th Century, before being rescued by Archdeacon Robert Johnson, who bought back the land and then obtained a Royal Charter from Queen Elizabeth I. This 1597 Royal Charter extended the purpose of the charity to helping both men and women, with a single Hospital able to accommodate up to 20 individuals.
During the late 18th / early 19th century the properties fell into disrepair, so that most buildings (with the exception of the original Chapel) disappeared when the Midland Railway was constructed in the 1840’s
From this point onwards the charity used its income to pay pensions to poor people who continued to live in their own homes. The payment of pensions ceased in 1976, on the advice of the Charity Commission, and at the same time the Privy Council removed the restriction on the number of beneficiaries. The governors began developing what was then known as ‘sheltered housing’. The first development of 12 flats was on a site in South Street, Oakham, purchased from the Royce Eventide Homes charity, with a similar property following shortly afterwards in Uppingham.
In 1984 a development of 28 flats, along with a common room, was built on land adjacent to the original chapel. Her Majesty the Queen and the Duke of Edinburgh visited the new development at St Anne’s Close on 16th November 1984.
In 1997 Her Majesty the Queen granted the Charity a Supplemental Charter enlarging the Governing Body and permitting the Charity to provide extra-care accommodation. This Supplemental Charter hangs on the south wall of the Chapel.
In 2011 the Hospital of St John and St Anne merged with the Archdeacon Johnson Almshouse Charity, bringing together the administration of 102 almshouse properties.
On 29th July 2014 The Prince of Wales, Patron, the Almshouse Association and the Duchess of Cornwall visited St Anne’s Close and the Chapel of St John.