This ‘20s Florida Luxury Hotel is Now an Elite Private School

Sitting between San Jose Boulevard and the St. Johns River, The Bolles School’s San Jose campus in Jacksonville, FL, is home to one of the state’s top high schools and one of the country’s best high school sports programs. But the school in its current form has only occupied its sprawling campus since 1961, and it all began with one key building.

That original building, known now as Bolles Hall, was constructed in the mid-1920s as the San Jose Hotel.

The hotel opened its doors at 7400 San Jose Boulevard in 1926. It was part of a community planned by the San Jose Estates Company, which intended to develop an upscale community featuring Spanish architectural elements. A large portion of the buildings constructed as part of the San Jose Estates project were designed by Jacksonville architectural firm Marsh & Saxelbye, including San Jose Hotel.

The hotel featured over 100 rooms, a spacious and beautiful lobby, and a scenic view of the St. Johns River. It was undoubtedly among the most luxurious offerings in southern Jacksonville at the time.

Unfortunately, the San Jose Estates project failed rather quickly, causing San Jose Hotel to tank within just a few years of opening. The hotel was sold off in a bankruptcy auction and purchased by Agnes Painter on behalf of the estate of Richard J. Bolles, which held a first mortgage on the property.

Painter, who had worked with Bolles and learned about the real estate industry, leased the building to the Florida Military Academy. In another stroke of bad luck for the building, the academy went bankrupt within three years.

Painter didn’t give up on the concept, though. She and her husband instead formed their own military academy, naming it for Painter’s former boss. From the beginning, the Bolles military academy acted as a boarding school for both local and international students, with Painter’s husband serving as the school’s headmaster.

The academy thrived for three decades as a military academy before deciding to drop the military aspect beginning with the graduating class of 1962. Within a decade, the school would start looking much more like it does today, as female students began to attend alongside the male students. Previously, the girls had been at an all-female school at what is now a satellite campus for Bolles.

Since entering its modern era, the school has expanded rapidly to fit its elite status. Today, the campus features dormitories for boarding students, two gymnasiums, tennis courts, a massive track and football field, and an elementary school campus in addition to the high school campus.

Thanks in large part to its grand facilities, The Bolles School has become one of the most prestigious private schools in the country. Its athletes have become NFL players and Olympic gold medalists, and its academic stars have gone on to attend top public and private colleges across the country. Its campus is routinely featured on lists of the most beautiful high school campuses in the country.

Despite the almost immediate failure of San Jose Hotel, its decadent building was able to be preserved and has now evolved into something that could last for many years to come.