Following his death in 1817, the Gratiot League Square was divided among his heirs, into a series of east-west strips each about 1,000 feet in width. By 1850, the principal landholders in that part of the League Square which now comprises the Oakland area were Peter Lindell, Paul M. Gratiot, Pierre Chouteau, Jr., David W. Graham, Solomon B. Sublette and the Berthold Estate.

Construction of the Pacific Railroad, now the Missouri Pacific, through the area in the early 1850's led to the opening of several subdivisions. Among the earliest of these were the subdivision of D. W. Graham's Sulphur Spring Tract in 1851 and Gratiot Place by Pierre Chouteau, Jr. in 1852. In the next year Cheltenham and Cheltenham Place were platted in the eastern portion of the Sulphur Spring Tract near Sublette Avenue. In 1857, Mount St. Louis was developed south of the New Manchester Road and east of Sublette Avenue. Farther to the west, Ringrose D. Watson subdivided his Glades Tract in 1852. It reached from Tamm Road west to McCausland between the present Dale and Mitchell Avenues.

In 1859, James McCausland opened a tract west of the Glades, running west to the western line of Gratiot League Square. Later, other tracts opened for development included those of James V. Prather, B. F. Buchanan and James C. Sutton.

By the 1890's, most of the subdivision activity was situated west of Hampton and along Manchester out to the city limits. This was obviously influenced by the presence of the railroad and the electric street car line on Manchester Avenue. There was a considerable development on both sides of Tamm Avenue south of Clayton Road, beginning in 1885 with Berthold's Subdivision and followed by several additions by the Shield's Realty Company in 1887-90. Blue's Subdivision in 1888 and Carlisle in 1890 were also platted in this vicinity.

Farther west and north of Manchester, several subdivisions were developed in the old Prather Tract, starting with Kleinschmidt's subdivision in 1884 and Samuel's in the next year. West of McCausland Avenue, Blendon Place was opened in 1885 and south of Manchester, along the city limits, Ellendale was developed in 1884, followed by Greenwood in 1891. However, most of the latter subdivision was in Maplewood.

After the World's Fair of 1904, more buildup occurred south of Oakland Avenue and east of McCausland. First to be developed was Victoria Place in 1906, followed by Oakland Terrace in 1907, Forest Park Home Place in 1908, Justin Place in 1910, and Dillenberger Place in 1911.

Following World War I, the Kraft Street Addition was platted in 1919. Activity during this period was also noticeable in the Benton and Glades areas where McDermott's Addition to Benton was opened in 1905, followed by Brockschmitt's Subdivision in 1911 and Winkle's in 1914. In 1916 Dale Avenue Heights and Wismann's Addition were developed. Not much subdivision platting occurred in the area during the 1920's and 1930's, the largest one in this period being Tamm Avenue Heights in 1927 and Parkhurst in 1937. After World War II, Louisville Heights was opened at West Park and Louisville Avenues and in 1953, Mitchell Terrace, the most recent to be developed, was opened.

In contrast to most of the outlying sections of St. Louis during the 1870's, the Oakland area was rather well built-up at that time. From Kingshighway westward to about the present location of Macklind Avenue, it was rural in character, with farms and fenced meadow land. There was no street along the south side of Forest Park where Oakland Avenue is today.

Clayton Road angled across the park and the western part of the Oakland area to continue its westward course into the county. Urbanization of the midsection of the area, from Macklind to beyond Tamm Avenue was due to access by the Pacific Railroad and New Manchester Road. A sufficient amount of buildup had taken place so that a Catholic church and a public school were established. In addition to a collection of smaller dwellings, several larger houses were located in the vicinity. Among them were the mansions of Henry H. and Doctor Charles B. Gratiot, as well as those of Eliza Billon and George A. Davis.

Cheltenham Station on the railroad was situated at Billon (now Hampton) Avenue, near some sulphur springs, with two hotels across from it on Manchester Road. To the south of the railroad was an industrial area of fire clay and brick works and the plant of the St. Louis Smelting and Refining Company. There were a small number of houses constructed by this time in the Benton-Glades district, near the present Dale and Plateau Avenues, and a Benton Station was located on the Pacific Railroad at Prather Avenue.