Ralph Stichter was the first, purchasing many acres at the northeast corner of Preston and Walnut Hill.

Famous architect Charles Dilbeck designed many monumental homes throughout the neighborhood in the 1930s and early 1940s.

[3] 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.

"[3] Doctors, entrepreneurs, industrialists, lawyers, and oil businesspeople moved to Preston Hollow.

[3] 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 a Preston Hollow corner property at Douglas and Averill Way.

In the 1930s, moving beyond Northwest Highway was considered "going into the sticks" and risky in terms of attracting affluent homeowners.

Preston Hollow was officially incorporated as a municipality in 1939, and DeLoache’s real estate office/Ebby’s Little White House turned into the town hall.

A neighborhood Facebook group called “Preston Hollow History” shares more historical information.

[1] Despite a 1948 U. S. Supreme Court ruling that state courts cannot enforce race-based restrictions on the occupancy of real estate,[5] a covenant was enacted in 1956 for 17 lots in the James Meaders Estates subdivision of Preston Hollow, which stated that only white residents were allowed to live on those lots unless they were "domestic servants of a different race or nationality in the employ of a tenant.

[7] Teardowns of mid-20th century ranch-style houses in portions of Preston Hollow began after land values increased in the 1980s.

[8] In September 2008, Preston Hollow returned to national headlines when New York Post gossip columnist Cindy Adams wrote a column claiming that U.S. President George W. Bush and his wife Laura had purchased a home in Preston Hollow.

[11] Politicians include former U.S. President George W. Bush,[12] former Dallas mayors Tom Leppert and Laura Miller and her husband, retired Texas legislator Steve Wolens;[13] and Christina Crain, the namesake of the Christina Crain Unit women's prison and former chairperson of the Texas Board of Criminal Justice.

Noted residents of Old Preston Hollow who are now deceased include ClubCorp founder Robert H. Dedman Sr.,[21] trial lawyer and Democratic Party fundraiser Fred Baron and his wife Lisa Blue Baron,[22] and Mary Kay founder Mary Kay Ash.

[3] Lisa Tanner of the Dallas Business Journal said, "The lines that define Preston Hollow are somewhat blurred."

She said that Preston Hollow had been commonly defined as being bounded by the Northwest Highway to the south, Royal Lane to the north, and Hillcrest Road to the east.

"[4] A map in the book Preston Hollow: A Brief History shows the boundaries, which were concluded by extensive research, as a backwards L shape with the Mayflower Estates area as “disputed”.

She added that "The so-called estate area on Preston Hollow's western side boasts large lots with grand entrances, rolling hills, and winding streets, and is home to some of the most luxurious mansions in Dallas.

Terry Box of The Dallas Morning News said in 1989 that the area north of Walnut Hill was "less prestigious" but "still affluent, with well-maintained upper-middle- and middle-class neighborhoods stretching to Royal Lane.

[27] Preston Hollow East consists of the single-family houses in an area bounded by the Dallas North Tollway, Hillcrest Road, Joyce Way, and Del Norte Lane.

[1] The Dallas Fire Department operated Station #41, which opened on January 16, 1958, in Preston Hollow.

The development includes two 20-story office towers that opened during a construction boom of the late 1970s and early 1980s.

Around that time, residents tried to pressure area politicians into making the development more low-rise and further removed from the Preston Hollow community.

[49][50] In Fall 2006, the attendance boundaries changed, with a portion of the former Walnut Hill zone being rezoned to Withers.

Judge Sam Lindsay ruled in November that the school's practices were not legal because they attempted to keep white students together even if minority students had to be placed in inappropriate courses; this ruling was miscited in at least one local paper as indicating that "all-white" classes had been created.

[55] Cary Middle was disestablished in 2020 after a 2019 tornado destroyed the campus, with Medrano and Franklin taking portions of the boundary.

Ursuline Academy of Dallas, a Catholic girls' high school, is located in the Estate area of Preston Hollow.