The English surname Headlee is an habitational name from any of various places, for example in Hampshire, Surrey, Worcestershire, and West Yorkshire, so called from the Old English termheathland, meaning “heather” and leah meaning “wood, or clearing.” The name is first recorded in 1273 when Alan de Hedleg is registered in the Hundred Rolls of Salop, (Shropshire). Willelmus de Hedelay was listed in the Poll Tax records of Yorkshire in 1379, as was one Margareta de Hedelay. A famous bearer of the name is Henry Headley (1765-1788) who became a well-known poet and critic publishing "Select Beauties of Ancient English Poetry" in 1787. Today there are approximately 1.200 bearers of the name Headlee living in the United States.
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