Originally 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 terrain with creeks and hollows extending westward from Preston Road. Preston Hollow originally extended from east of Preston Road, and a little north of Walnut Hill Lane, west of Midway Road and southwest of Northwest Highway.
In 1945 Preston Hollow residents voted to join with the city of Dallas and the municipality was annexed to Dallas soon thereafter. In 1956, the neighborhood association's covenant stated that only white residents were permitted to live in Preston Hollow but this policy is reported to have never legally been enforced and was repealed in 2000.
Preston Hollow is very well-known for its generous estate homes, built by renowned architects, some dating back to mid century and the early 1900s.
Preston Hollow is known as one of the wealthiest areas of Dallas. It is also one of the wealthiest areas in Texas. Within Preston Hollow you can find some of the most expensive homes in Texas as well as some of the state's wealthiest residents. Currently houses range from $1,000,000 tear downs up to $50,000,000 estates.
Prominent longtime residents of Old Preston Hollow include Dallas mayor Tom Leppert, Dallas Mavericks owner Mark Cuban and its President Terdema Ussery, former Dallas Cowboys Roger Staubach and Chuck Howley, Stream Energy Chairman Rob Snyder, billionaire investors Harold Simmons and T. Boone Pickens, sports team owner (Dallas Stars, Texas Rangers and Liverpool F.C.) Tom Hicks, software developer Larry Lacerte, noted trial attorney and Democratic party fundraiser Fred Baron and ex-Dallas Mayor Laura Miller and her husband Steve Wolens (retired Texas legislator).
Former noted residents of Old Preston Hollow include the late Robert Dedman Jr., former American Airlines chairman Bob Crandall, and the late cosmetics magnate Mary Kay Ash.
Former President George W. Bush, Presidential candidate billionaire Ross Perot, Dallas Cowboys football coach Wade Phillips, and Dallas Stars player Mike Modano also live in the greater Preston Hollow area.
On December 4, 2008, the then-President George W. Bush, announced that he would be moving back into the area upon leaving office. After this, the street of his occupancy, Daria Place, became gated, with 24 hour gate security for his safety.