Jax Evolved: From San Jose Hotel to The Bolles School

Sitting between San Jose Boulevard and the St. Johns River, The Bolles School’s San Jose campus is home to one of the state’s top high schools and one of the country’s best sports programs.

While at this point it’s hard to imagine anything other than Bolles’ rowdy Friday night football games lining that stretch of San Jose Blvd., the school has only occupied the campus since 1961.

The original building, known now as Bolles Hall, was originally constructed in the mid-1920s.

In 1926, the San Jose Hotel opened its doors at 7400 San Jose Blvd. It was part of a community planned by 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 the 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. As a result, San Jose Hotel tanked 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, the academy went bankrupt within three years as well.

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 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 the Bolles Bartram Campus.

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.

While San Jose Hotel may have been a bust, its original building isn’t going anywhere as long as Bolles continues its winning traditions.