Sometime between 1900 and 1910 a prominent financier named George A.J. Howard envisioned a beautiful tranquil park as a setting for family homes such as one sees in the English countryside in what was then an undeveloped and rural area about half way between the city center (now Downtown LA) and the coast.

The development was constituted as a private square. Both the homes and the streets would be privately owned. At that time there were dense groves of bamboo in the area which needed to be destroyed before trees and gardens could be cultivated. Intervening walls or fences were discouraged so that one garden ran into another creating a park-like setting. Windsor Square was the first area in the city to have the power lines below grade, an extraordinary innovation for 1911.

To make sure that the homes were significantly upscale as befitted the exceptionally beautiful setting, deed restrictions were set at a minimum cost of $12,550. per home, an enormous amount at the time. Many outstanding architects designed homes for the area including Paul Williams and A.C. Martin.

As a result, many of the city's elite moved west to Windsor Square including Howard and Norman Chandler who took up life-long residence with his wife Buffy on Lorraine Blvd. Oil magnate John Paul Getty bought a property on Irving Blvd. that is now Los Angeles' official mayor's residence.