Windlesham is not mentioned in the Domesday Survey of 1086 and it was first recorded in 1178. The meaning of the name is uncertain but it possibly refers to 'windel' from the Old English meaning 'winding'. The Windle Brook flows nearby, although there is no evidence for the antiquity of the name. Alternatively, 'Windlesham' could derive from a single person, Windel, who may also have given his name to Windsor. The Royal Family changed their name to Windsor during the First World War and it is interesting to speculate that this scattered Surrey village may have been named after the same individual.

Windlesham belonged to the priory of Broomhall in Berkshire until it was surrendered to Henry VIII in 1522. The following year it was granted to St John's College, Cambridge. There was a medieval church at Windlesham which was rebuilt in 1680 following a fire. This 17th century church survives but was much altered in two stages in the Victorian period. There are also several houses dating from the 16th to the 18th century to be found in the area. There is no railway station at Windlesham, the nearest being at Bagshot, which opened in 1878.

Much of Windlesham lies on the Bagshot sand and is still heathland to this day. Because of the acid nature of the soil Windlesham developed in the 19th century as a major area of nursery gardens for the cultivation of rhododendrons, azaleas and other garden shrubs. The Victoria County History of Surrey recorded in 1911 that at the time two large nurseries, 'those of Messrs Fromow and Messrs Waterer [were] employing a great deal of labour'.

Windlesham lies close to the M3 but still manages to retain its rural character.

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