Shaw never married and did not live extravagantly. The income from his business, therefore, soon provided him with a surplus of funds. He invested the income from his hardware business shrewdly, buying a great deal of real estate in the St. Louis area. Shaw bought many commercial properties and other lots in the city. He also bought large tracts of land in the outlying areas. One of properties consisted of a tract in an area previously known as the Prairie de Noyes. In his later life, Shaw wrote the following account of the first time he saw this land in the 1820s.
For a distance of nearly two miles from where Tower Grove Park is now laid out to Taylorwick station, or rather the pond still existing there , no trees were growing, except two or three venerable Cottonwoods (Populus Canadensis) in the low ground, on the water course running to Rock Spring, and thence to Chouteau Millpond; on this water course were a few plants of the (Nymphea ordorata Ait.) sweet-scented Water Lily, and a clump of Hazel Bushes on the rising ground, where the grove at the garden now exists. The prairie was grown over with a tall natural grass Andropogon, prairie grass, with an occasional patch of the wild Strawberry (Fragaria Virginiana) of which neither a tuft of grass or a plant of the strawberry can now be found.