In 1924 Ira De-Loache bought a 56-acre farm. Preston Hollow's first lots were carved out of the former farm parcels. De-Loache and Al Joyce developed Preston Hollow, with development largely occurring in the 1930s. At first Preston Road was the area's only connection to Downtown Dallas. Terry Box of The Dallas Morning News said that the Northwest Highway "was nothing more than muddy right of way." The area that would later become Preston Center was a Dairy Farm in the early to mid-20th Century. 

The developers intended Preston Hollow to be what Box said was "more than a flatland suburb on the fringes of a new and growing Dallas."Doctors, entrepreneurs, industrialists, lawyers, and oil businesspeople moved to Preston Hollow. Many built country-style estates that housed horses and stables. A private school which later became St. Mark's School of Texas opened in the area.

Incorporated as a municipality in 1939, and provisioned by the Preston Road Fresh Water Supply District, the North Dallas town of Preston Hollow was named for the deep wooded area with creeks and hollows extending westward from Preston Road. The bramble in Preston Hollow was unique in the Dallas area and all home builders in the area were to preserve it as part of the covenant.

In the early 1930s during the Depression, Edward James Solon, the treasurer of a company called Interstate and the partner who came with Karl Hoblitzelle from Chicago to Dallas, purchased the first Preston Hollow corner property at Douglas and Avrille Way. Mr. DeLoache was to build a Dillbeck designed house on the property. This Tudor styled home was considered the first of many large homes built in what is now termed the Old Preston Hollow area. Originally, there was one large house in the area further over by the pond near Avrill, but it was considered as having been part of the farm. In the 1930s jumping across NW Highway was considered going into the sticks and risky in terms of attracting the affluent during the Depression. Later many people said that E.J. Solon started the North Dalllas migration. Preston Hollow originally extended from east of Preston Road, slightly north of Walnut Hill Lane, west of Midway Road and southwest of Northwest Highway. In 1945 Preston Hollow residents voted to join the city of Dallas, and the municipality was annexed to Dallas shortly thereafter.

In 1956, the neighborhood association's covenant stated that only white residents were allowed to live in Preston Hollow. This policy, though never legally enforced, and ruled unconstitutional by the US courts in the 1960s was repealed in 2000. That restrictive language is included in thousands of association covenants.