Windsor Hotel

The Old Windsor Hotel

The Windsor Hotel was built in 1875, catching Jacksonville’s tourist boom with a firm grasp. A renowned vacation spot for those looking to escape the cold, Jacksonville saw an average of 50,000 to 73,000 visitors on a yearly basis at the time. The Windsor was also open to soldiers awaiting orders to Cuba during the Spanish-American War in 1898. Deemed one of Florida’s finest hotels and prized for its unusual architecture, the three-story hotel featured a lavish dining hall complete with an extravagant centerpiece and balcony, spacious rooms, office space, parlors, and a golf course tucked amidst scenic Florida nature. 

The St. James Hotel on the site of the old Cohen Brothers Department Store, the Carleton House located on the northwest corner of Market and Bay Streets, and the Windsor vied for the bulk of Jacksonville’s tourist trade at the time. All three were destroyed in the Great Fire of 1901. The St. James and Carleton were never rebuilt, but owners Abbie Dodge and Frank Cullen began work on a new Windsor in August 1901.

Reconstruction After the Fire

Constructed a new brick, stone, and steel in a “magnificent Spanish Renaissance style to cover the entire block between Hogan, Monroe, Duval, and Julia streets,” as reported by the Times-Union in 1966, the revamped Windsor featured a red tiled roof, grand columns, and birch and mahogany woodwork.

A brochure put out by the Hotel Windsor said, “The views in this booklet show you the delightfully unusual character of the building and environments, but only a stay at the WINDSOR can bring you a realization of the pleasures to be derived from a Winter in Sunny Florida. Our service is nearly as perfect as we can make it. Our desire—to help you enjoy Jacksonville and Florida.”

Reopened in 1902, it became a hotspot for royalty, celebrities, and presidents, notably Franklin D. Roosevelt, who visited in 1933. Several organizations also held their first meetings in the hotel, including the Women’s Club of Jacksonville in 1895, as well as the Jacksonville Rotary Club in 1912, and the Kappa Kappa Gamma Alumni Association in 1942.

Decline and Demolition

As Jacksonville’s tourist boom came to a slow end, the hotel eventually fell into bankruptcy. In its last few years, the hotel became home to sixty retired residents. Deemed one of Jacksonville’s last standing pieces of evidence of fame and popularity, the hotel’s 48-year legacy came to an end when John E. Meyer, president of the Meyer hotel chain, which owned the Windsor, announced that it would be closed and demolished. He said, “The age and obsolescence of this property precluded the possibility of any further profitable operation as a hotel.”

Demolition began in May 1950. In 1955, I. Morris, vice president of the Cuyahoga Wrecking Co., told the St. Petersburg Times that the hotel concealed the strangest thing he had ever uncovered during a demolition—a hidden underground room packed with illegal whiskey.

The property served as a parking lot until J.C. Penney and Woolworths built stores at 320 North Hogan Street in 1955. Both stores saw closure in 1980. The Robert Meyer Hotel opened in 1959 and occupied the space facing Julia Street. It featured a marble lobby, 563 guest rooms, restaurants, a jewelry store, and an outdoor pool. It went bankrupt in 1977 and reopened as a Holiday Inn in 1980 before closing in 1982. The Holiday Inn was imploded in February 1998. Today, the Bryan Simpson United States Courthouse, which opened in 2003, stands where the Windsor Hotel once stood.