In 1926, the city of Portland expanded Sandy Boulevard through northeast Portland to become a four lane highway, linking Portland with all points east. This expansion allowed much more development to take place in the Parkrose district, which at the time was primarily farmland. Beneath the eastern shadow of Rocky Butte, there existed a relatively untouched section of land that was a thick semi-old growth conifer forest. A triangular plot was purchased by the Columbia Realty Company and soon thereafter, the Maywood Park subdivision was plotted.
In 1930, Columbia Realty was bought out by Commonwealth, Inc. Under the direction of Robert H. Strong, Commonwealth took control of Maywood Park. The intention of the new developer was to build a neighborhood that would be of the same class as the Laurelhurst and Eastmoreland neighborhoods in southeast Portland.
Maywood Park grew slowly during the Great Depression and throughout the 1930s. By the end of the decade though, home sales began to take off and in March 1939 there were 23 new homes under construction totaling a value of about $140,000, quite a large sum at the time. People were drawn to the neighborhood because it was far from the city center, but was easily accessible by automobile using Sandy Blvd. Another large draw was that the area was unlike the immediate surrounding area, Maywood Park was completely shrouded by huge conifer trees.
During World War II, the Federal Government constructed war worker housing in the surrounding area, known as Parkrose. This development was far different from the homes in Maywood Park with their mixed and sometimes eclectic styles of architecture, beautiful landscapes and tree shaded surroundings.