Henry fitz Ailwin de Londonstane (c.1135– 19 September 1212) was an English merchant and landowner who served as the first Lord Mayor of London from 1189 to 1212.

[2] Of mainly English rather than Norman descent, fitz Ailwin's family had been active in the commercial and civic life of London for generations.

His grandfather Leofstan (c. 1100–1150) was probably the portreeve of London, who in 1108 was involved in the foundation of Holy Trinity Priory, Aldgate.

Alward died without issue, and Derman's heir was his brother Leofstan, father of Ailwin or Elwyn, and grandfather of Henry FitzAilwin.

[15] Since the devastating fire of Stephen's reign had gutted all London, FitzAilwin was decided that some efforts should be made to bring in Regulations to build houses in stone.

[17] As parliament's powers grew it developed into twelve men chosen at full Hustings, originally held in FitzAilwin's house, that laid the foundations of the jury system at assizes.

[2] Henry fitz Ailwin's main home and business headquarters was in a large house behind St Swithin's Church (a church since demolished), near London Stone accessed off both St Swithin's Lane or Candlewick Street, now Cannon Street.

Henry's son Alan married, and is known to have had at least one child, Robert FitzAlan,[23] and is buried at Robertsbridge Abbey in East Sussex.