Its name derives from the Windle Brook, which runs south of the village into Chobham, and the common suffix 'ham', the Old English word for 'homestead'.

The neighbourhood has yielded bronze implements, now in the Archaeological Society's Museum, Guildford, and a certain number of neolithic flints.

Windlesham was once a small community within Windsor Great Park, built as a remote farming settlement around undulating heath, similar to Sunninghill.

At Ribs Down in the north in private Updown Court (now called Oakwood) and adjoining gardens, land reaches 99 metres above sea level with a minimum descent (notch/col) of 31 metres, ranking 35th of 36 Surrey hills listed in the national hill-climbing database and the tallest private hill in Surrey.

[3] Of Windlesham, Malden wrote: The old road had been the source of great prosperity in Bagshot till it was superseded by the railway.

In the next year Windlesham was granted to St. John's College, Cambridge, who still held it in 1911[3] In 1911, the village was, due to Surrey Heath, described as almost entirely modern, in much the same way as Wentworth, Surrey's landscape was tamed approximately at the turn of the 20th century, being naturally heather, gorse and fern and ideal for grass and laid out evergreen trees.

Windlesham Field of Remembrance is owned, funded and run by the village community via a board of volunteer trustees.

[6] Valley End is a hamlet and chapelry in the Borough of Surrey Heath in Surrey, England, 0.5 miles (0.80 km) east of Windlesham, so similarly is about 15 minutes drive from the South West Main Line at Woking to the southeast and from Sunningdale on the Waterloo to Reading Line to the north.

[17] See Bagshot for this developed part of the civil parish, which has the greatest concentration of homes, shops and businesses compared to Windlesham and Lightwater.