The first mention of the manor at Lollebrok occurs in 1376 when Thomas de Lollebrok appeared in court to exhibit his entitlement to it. Variously known as Lollebrok, Lollebrookes, Lolbrooks, Lowbroke, Lowbrook, Lowbrooks, Lullibrooke, Lyllebrok, or Lyllebrokes, the name Lillibrooke appears to have been the original title of the manor and the present farmhouse is therefore known as Lillibrooke Manor. It means "Babbling Brook". Whilst the estate may have appeared as a late medieval manor in Bray, the family had previously acquired lands in adjoining Cookham: as early as 1292 when Walter de Lillebrok obtained a messuage, lands and rent from Joan de la Lane of Ellington (the old name for Maidenhead). The family prospered in the area for over a hundred years until King Richard II's reign when Thomas Lolebrok backed the ill-fated monarch and lost his lands as punishment for his blind loyalty. By 1412, the manor had passed into the hands of the well-known Martyn family of Athelhampton House in Dorset. The present building at Lillibrooke was constructed in about 1490 and it's possible that they spent time there when visiting the Royal Court in Windsor. By 1541, however, the family's young heir, Robert Martyn had sold up to the trustees of Sir Thomas Englefield of Englefield House (near Reading). The estate was purchased for the knight's widow, Lady Elizabeth, and she may have lived at Lillebrooke while her son was installed at Englefield. It continued as one of the family's major secondary residences after her death and was central to the 1594 marriage settlement agreed between Francis Englefield and Jane, the sister of Viscount Montagu. During Cromwell's Commonwealth, the estate was finally confiscated from the couple's fifth son, William, as penalty for his Catholic beliefs. In 1656, it was purchased by the new tenant, Henry Partridge, a citizen and cooper of London. It remained in the family until the middle of the 19th century when the estate was bought by Charles Pascoe Grenfell along with several other manors in the area.