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Until the 1930s Shirley consisted of a few hamlets between farms and the estates of the large houses. These included Spring Park, Monks Orchard, Shirley Park, Shirley Lodge and Ham, names which are reflected in the names of neighbourhoods today. Originally part of Addington and contrary to popular opinion, Monks Orchard is not named after a monastery in the area, but probably commemorates a family named Monk, who owned some of the land at one time. When Lewis Lloyd acquired the land and had a mansion built in 1854, he adopted the name of a local wood, "Monks Orchard", for the whole estate.

Lloyd's Monks Orchard House was one of the most substantial mansions in the Croydon area. It had 19 bedrooms, a billiard room, library, and numerous other rooms. The Dining Hall alone was over 36 by 21 ft (11 by 4 m). The estate covered a huge area, 1,540 acres, stretching northwards from the Wickham Road almost to Elmers End, southwards nearly as far as Addington, and eastwards across the Borough boundary into West Wickham. It also included several other major residences, such as Spring Park; farms, including Eden Park, Ham Farm, Shirley Farm, Spring Park Farm and Oak Lodge Farm; two dozen or so cottages; The Rising Sun, The Cricketers and the White Hart; and Beckenham Golf Course. As late as 1923, the area was described in the following way:

The Estate, which has an extensive frontage to the road between the villages of Shirley and West Wickham, is delightfully rural in character, typifying that which is best in the unspoiled English countryside... The land seems adapted by nature for those who are seeking country houses not too far from London, being already park-like meadow land, well timbered, and dotted with coppices; thus affording almost unlimited scope for imagination, and taste, in laying out grounds, by utilising the natural advantages already there