While Henry Shaw began to subdivide his extensive land holdings as early as 1855, the earliest residential subdivision in the area was McRee City in 1869. In 1878, Shaw platted his Grand Avenue Addition, bounded by Grand, Shaw, Spring and McRee Avenues. It was Shaw's idea to duplicate a street he knew in his native England. The charming result consists of an oval drive around a parkway, with a fountain near its south end. This fountain formerly graced the eastern end of Vandeventer Place. Bordering the drive are ten Victorian brick houses dating from the 1880's, with high windows and white painted front porches. They each have one bricked up window, following an English custom of closing off windows, since taxes once were assessed according to the number of windows in each house. Designed by George Ingham Barnett, their interiors have high ceilings and sliding doors of heavy wood. They were built as rental property, but upon Shaw's death, certain houses were willed to the Garden. Exceptions were houses left to Shaw's housekeeper and relatives. Shaw Place became a private street in 1915.

Following the opening of Tower Grove Place in 1886, broad sections of land were platted for development in 1888-89. These included Tyler Place, which with the exceptions of Flora Place and the Bompart strip along Magnolia Avenue, reached from Grand to Tower Grove and from Magnolia to Shaw Avenue. Dundee Place, platted in 1889, covered the area between McRee and Park Avenues, westward from Grand to Old Manchester Road. Shaw's Flora Boulevard subdivision, popularly known as Flora Place, was platted in 1901 and within a few years was lined with fine houses. In the years between 1911 and 1915, several sections were opened in Shaw's Lafayette Avenue Addition between Shaw and McRee, west from Grand to Tower Grove. Magnolia Place was opened in 1916, as was Shaw's Vandeventer Avenue Addition, north of the Garden. Gurney and Heger Courts were opened in 1922-23, followed in the latter years by the Shaw's Garden Subdivision, across Alfred Avenue from the west side of the Garden. It had been under-developed Garden property prior to subdivision.