It lies halfway up the northern scarp of the Chilterns, about half a mile from the parish church of Monks Risborough.

The hamlet's name is first found in the form White Cliff in the eighteenth century, referring to the white chalk cliff above the road to the east of the hamlet,[1] which has the Whiteleaf Cross cut into the chalk on the side of Whiteleaf Hill above it, making an important landmark for miles around.

Whiteleaf is home to Monks Risborough Cricket Club and the 9-hole Whiteleaf Golf Club, both of which lie slightly south-east of the main road through the village, which follows the path of the Upper Icknield Way.

The cricket club celebrated its centenary in 1993 and a book covering its history was published.

Children's writer Kevin Crossley-Holland grew up in Crosskeys, Westfields (a cottage now called Woodside).