Jarvis and Conklin, a Chicago investment firm, purchased of land near Lake Roland in 1891 and founded the Roland Park Company with $1 million in capital. Not long after, the Panic of 1893 forced Jarvis and Conklin to sell the Roland Park Company to the firm of Stewart and Young. Despite the dire economics after 1893, Stewart and Young continued investment in the development. The Roland Park Company hired Kansas City developer Edward H. Bouton as the general manager and George Edward Kessler to lay out the lots for the first tract. They hired the Olmsted Brothers to lay out the second tract, and installed expensive infrastructure, including graded-streets, gutters, sidewalks, and constructed the Lake Roland Elevated Railroad. The company consulted George E Waring, Jr. to advise them on the installation of a sewer system. Bouton placed restrictive covenants on all lots in Roland Park. These included setback requirements and proscriptions against any business operations. Bouton and the Roland Park Company initially intended to include covenants to exclude blacks from the development, but on advice of counsel did not include them in the deeds. The Roland Park Company would later insert these covenants into deeds in Guilford, Homeland and Northwood. It was a modern development, electricity for lighting throughout the neighborhood as well as gas for cooking and lighting. Water came from artesian wells dug up to, nearly of water mains were constructed, in addition to of roadways, and of sidewalks. Bouton and some Baltimore investors purchased the interests of Roland Park and reorganized the company in 1903. Frederick Law Olmsted, Jr. cited Roland Park as a model residential subdivision to his Harvard School of Design students. Duncan McDuffie, developer of St. Francis Wood in San Francisco, called Roland Park "an ideal residential district." Jesse Clyde Nichols had found inspiration in Roland Park when he was planning the Country Club District of Kansas City. Nichols continued to refer to Roland Park as an ideal residential development when he counselled other residential developers.
Roland Park Shopping Center was built at the corner of Upland Road and Roland Avenue in 1896 in the English Tudor style. Developed by Roland Park Company President Edward Bouton and designed by Wyatt and Nolting, it was originally planned as an apartment and office building with a “community room” for civic functions on the upper level. It opened in 1907 as shops. It has been credited by Guinness World Records as the world's first shopping center. Since it had only six stores, qualifying today as a strip mall, other, larger centers have received more recognition as “firsts”, such as Market Square in Lake Forest, Illinois and the Country Club Plaza in Kansas City, Missouri, the first uniformly-planned regional shopping center.