Through 1913, while Sherman was engaged in the real estate market, his primary concerns were his street railroad operation. The trains of course brought people near to the land he owned. Much of what he owned was in Sherman, what is now West Hollywood. At this time, Sherman would have sold parcels of land, but was not involved in the actual construction of homes.

In 1913 Sherman sold his street railroads to Henry Huntington, who incorporated the lines into his Red Car system. At about the same time Sherman entered into a syndicate with Harry Chandler and Otto F. Brant to form Los Angeles Suburban Homes. This was the group that bought from the Lankershims and subdivided the southern half of the San Fernando Valley. Sherman’s area included Owensmouth, which was later renamed Canoga Park. Sherman was also involved, with Ralph Chandler in the Los Angeles Steamship Company.

In addition to the above, Sherman was engaged in operations of the Colorado River Land Company, which operated an enormous ranch in Norther Mexico, and after 1912 spent time at Tejon Ranch, in which he had a financial interest.