His best known works include Crowhurst Place and Old Surrey Hall, both in Surrey, England, and the design of Westbury House (built 1904–10; additions constructed in 1915–16), at Old Westbury Gardens, in Long Island, New York, for John Shaffer Phipps (the heir to a steel fortune).
Phipps showed him the plans for the townhouse he was building on Fifth Avenue in Manhattan, telling Crawley about his dissatisfaction with the architects' work.
Crawley took an interest in the project and made recommendations for a redesign, leading Phipps to invite him to New York City and ultimately to hire him to complete the design of the house.
[2] Henry Phipps' son, John "Jay" Phipps, developed an appreciation for Crawley's design ideas while working with him on aspects of his father's Manhattan house, leading him to ask Crawley to undertake the design of a country estate house for the 175-acre (71 ha) tract on Long Island that he had purchased in 1901.
Crawley played a major role in landscape design for the surrounding property, as well as additions and renovations that were made to the home after John Phipps and his family moved in.