During the 1930s, “ Greenbelt ” communities were planned and built by the federal government outside three major metropolitan centers – Baltimore, Cincinnati, and Milwaukee. The projects demonstrated the value of urban planning, while providing employment opportunities and relieving the shortage of low income housing.

The Resettlement Administration of the U.S. Department of Agriculture purchased 3,400 acres of farmland and woods for the development of Greendale. In May 1938, the first housing units were occupied. There were 572 living units in 366 buildings, half of which were single family homes built of cinder block on poured concrete foundations. Most houses were built on cul-de-sacs which discouraged heavy traffic while necessary vehicles used three major thoroughfares. The community’s focal point was designed to be the Greendale Village Hall, built in a style reminiscent of Colonial Williamsburg.

The sale of the Greenbelt towns was authorized in 1949 and Greendale was purchased by the Milwaukee Community Development Corporation in 1952. Original tenants were given first option to purchase their Greendale homes.