Lakewood Ranch is the new kid on this list — it barely existed as a place until the 1990s. Its roots go back to the early 1900s, when Milwaukee entrepreneur John Schroeder began buying up thousands of acres for timber and cattle ranching. In 1922, the Uihlein family — owners of the Schlitz Brewing Company, "the beer that made Milwaukee famous" — bought the property, reportedly for about $2 an acre, and kept it as a working ranch (cattle, citrus, sod, turf, and mining) for decades. It stayed largely empty except for one brief ghost town: Lorraine, a tiny timber-and-turpentine company town established in 1915 at a railroad stop, dissolved by the mid-1920s.
The ranch company, Schroeder-Manatee Ranch (SMR), made its move in the 1970s when it learned the proposed I-75 route would pass just west of the property — and in February 1994 it formally shifted into community development. The first homes, in Summerfield Village, were built in 1995, starting around $89,000. (It was originally to be called "Cypress Banks" until a marketing firm suggested Lakewood Ranch — lakes, woods, ranch — and it stuck.)
Today Lakewood Ranch spans 35,000-plus acres across Manatee and Sarasota counties, with more than 72,000 residents in 30-plus villages, its own Main Street, a business park, polo grounds, and even its own U.S. Postal Service zone — "Lakewood Ranch, Fla." It's been ranked the bestselling master-planned community for all ages in the U.S. for seven years running, and it remains part of a working ranch — you can still see cattle grazing as you drive across University Parkway.