Howard envisioned a beautiful tranquil park as a setting for family homes built in a countryside style in what was then an undeveloped and rural area about halfway between the city center (now Downtown LA) and the coast.

[2] Many outstanding architects designed homes for the area, including Paul Williams, John M. Cooper, and A. C. Martin.

As a result, many of the city's elite moved west to Windsor Square, including developer Howard and Norman Chandler, who took up lifelong residence with his wife Buffy on Lorraine Boulevard.

[3] Though the homes that fronted Wilshire Boulevard have been demolished to make way for commercial buildings, an active neighborhood association has succeeded in preserving the character of Windsor Square.

[6][7] The Los Angeles Times Mapping L.A. project extends Windsor Square's eastern boundary slightly, to Wilton Place.

About a third (33.5%) of the residents were born outside the United States, considered a high ratio for Los Angeles, the most common country being South Korea at 57.7%.

By 1989, though, criminal activity had spread throughout the surrounding neighborhood, and the Windsor Square Property Owners Association requested that the park is closed at sunset and that it be fenced, gated and locked.