The square is named for Sir Richard Cloudesley, who had an estate here from the early C16th. In 1811 the Estate Trustees were permitted to let building leases and the Cloudesley Estate, also called Stonefield, was planned from 1812. Cloudesley Square, begun in c.1825, was the centre of the estate, with Holy Trinity Church built in 1826-29 to serve the growing population. Around the church is a hexagonal railed garden, essentially a strip of grass with a path and a number of mature trees.
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Sir Richard Cloudesley had an estate here from the early C16th and gave c.16 acres of an area called Stonyfield to the parish in 1517. His will left numerous charitable bequests as well as masses to be said for his soul. Contemporary sources at the time of his death describe his distressed state, his body 'restless, on ye score of some sinne by him peraddventure committed' and an exorcism was carried out at his burial at St Mary's (q.v.).
An Act of Parliament of 1811 allowed the Cloudesley Estate Trustees to let 99-year building leases and the Cloudesley Estate, also called Stonefield, was planned from 1812. Carpenter John Emmett took most of the leases and began the estate along Liverpool Road, acquiring the rest of the site in 3 leases between 1824-6. Cloudesley Square was the centre of his estate and was begun c.1825, with terraces of 1826 surviving today. Most of the estate was auctioned in 1837 with the Trust keeping an interest in part of the area including the west sides of Cloudesley Square, eventually selling long leaseholds in the 1970s.
Holy Trinity Church was built in 1826-29 to serve the growing population and was designed by Sir Charles Barry, the third of his Islington churches. The stained glass east window by Willement of 1828 depicts Sir Richard Cloudesley kneeling. It served as the district church until the 1850s when St Andrew's at Thornhill Square (q.v.) was built. In the 1960s it was declared redundant and in 1980 was leased by the Pentecostal Sect as the Celestial Church of Christ. It is surrounded by a strip of garden, largely grass, a few notable trees and with a path around the church and a few shrubs by the door to the west side. The railings were restored in 1980. Most of the surrounding houses are C19th.
Mary Cosh, The Squares of Islington Part II: Islington Parish, (London, 1993); Mary Cosh, Barnsbury, (London, 1981); Bridget Cherry & Nikolaus Pevsner, The Buildings of England: London 4: North (Penguin, 1998)