Penn Street gets its name from a combination of two old words. ‘Penn’ means an enclosure, although some books say it’s Celtic for hill. ‘Street’ derives from a Saxon word meaning a road used by the Romans. There was such a road running from a nearby villa to a main Roman road south of Beaconsfield.
The village and the surrounding area stand on part of the ancient Wycombe Heath, 4,000 acres of common land, comprising heathland and woods. Some of the houses that line the road date back to the 15th, 17th and 18th centuries. The local church, Holy Trinity, was built in 1849. In May 1913 the church organ was set alight by suffragettes.