There is evidence of settlement in Prestwood from the Middle Ages, when the village was mainly covered in oak, beech and ash trees.

[1] The first vicar of Holy Trinity planted a set of ornamental trees behind the church; this now forms Prestwood Park.

[1] The main industry in Prestwood continued to be agriculture; orchards were created and much of the fruit was sold to traders in London.

The arrival of the railway in Great Missenden improved access to central London, leading to Prestwood becoming a commuter village.

[citation needed] However, the expansion of the village was not without its setbacks; houses were built in Perks Lane, destroying the orchids that grew there.

Wren Davis Dairy opened on Wycombe Road, winning award nationally for the quality of its milk.

[3] Today the dairy owns several acres of fields in the north and west of Prestwood, on which its cows still graze.

[citation needed] His four eldest sons took over the business upon his death in 1932; when it closed down in the 1980s, the steel blood bins were buried on land now belonging to Prestwood Junior School.

Gaybird Ltd supplied pheasant chicks and eggs to shoots throughout the country, raising the birds in fields stretching from Prestwood as far away as Dunsmore, near Wendover.

[1] Two bombers collided over Prestwood with much of the wreckage falling close to Nanfans (or Nafans) Farm on Honor End Lane.

[1] A plaque commemorating the tragedy can be found outside the Limes Tea House at the local garden centre, Hildreths of Prestwood.

[1] Despite the continued growth of the village population, four pubs closed down – the George, the Weathercock, the Golden Ball and the White Horse.

[citation needed] In January 2000 a further elderly home consisting of 30 flats was opened, called Cherry Orchard,[4] leading to an increase in the number of retired people living in the village.

In the early hours of Saturday 9 December 2006, a large fire swept through the Cherry Orchard residential home, killing one elderly woman and forcing 12 others to be rescued.

The opening helped to revitalise Prestwood's economy and continues to attract people from the surrounding area.

The village is also home to one of the largest gymnastic clubs in Buckinghamshire, which is held at Prestwood Junior School on weekday evenings and Saturday mornings.