1. Brooklyn’s Last Post-Civil War Cottage

328 Chelsea Street

During much of the Civil War, Jacksonville was occupied by the Union Army. A large portion of the Union’s soldiers were former enslaved who had joined the cause to fight the confederacy in order to provide freedom for their loved ones. After the end of the war, many stuck around and settled in the northwestern portion of Brooklyn, establishing the community as a reconstruction era African-American community.

Failing in its 2013 request to become recognized as a local historic district, much of the storied Gullah Geechee neighborhood has been erased from existence with the recent emergence of Brooklyn as a popular location for urban living. With gentrification in full effect, this boarded up and abandoned post civil war cottage (also known as the Buffalo Soldier’s House) is the last still standing, providing a direct link with the city’s Reconstruction era past.

2. Claude Nolan Cadillac Building and Garage

937 North Main Street

Designed by Henry J. Klutho and completed in 1912, this building was originally constructed as a car dealership for Claude Nolan Cadillac. According to Jacksonville’s Architectural Heritage by Wayne W. Wood, Nolan is credited for being the first automobile dealer to sell cars on installments in 1910, which is now an industry-wide standard. In addition, Nolan was the first native Floridian to fly over the state in an airplane and first person to drive from Miami to Key West. Altered beyond recognition, the future of this Prairie-style Klutho structure could be in danger due to contamination issues involving the nearby Hogans Creek and the site’s past history as a coal gasification plant.

3. The Florida Times-Union

1 Riverside Avenue

Dedicated with great fanfare on April 15, 1967, 1 Riverside Avenue was initially dubbed as an “ultra-modern new riverfront complex”. The centerpiece of the riverfront complex is a 55,500-square-foot, five-story modern office building. Now vacant, the building will most likely be razed this year and replaced by a proposed $250 million retail, office, restaurant and apartment project by Atlanta-based developer Jeff Fuqua.

4. Genovar’s Hall

636 - 648 West Ashley Street - Genovars Hall / Shotgun Homes

Initially constructed as a market for Sebastian Genovar in 1895, this LaVilla building predates the Great Fire of 1901 and is ground zero when it comes to paying homage to the neighborhood’s cultural and musical contributions to the early development of ragtime, jazz and blues genres. Originally built across the street from 19th-century madam Cora Crane’s Hotel de Dream, this three story structure housed a variety of businesses during the ragtime, jazz and blues age of the early 20th century. In 1913, it housed a restaurant owned by M. Kinsey Bellamy. In 1931, the Wynn Hotel opened in the building’s upper floors, while a jazz club called the Lenape Tavern and Bar opened on the first floor.

Operated by Jack D. Wynn, the hotel became a favorite spot of Louis Armstrong when visiting LaVilla. Wynn’s son, Daniel Ruben Wynn, is a noted local artist who had his work exhibited at the Center of International Culture in Paris, France in 1975. In addition to Armstrong, others who performed at the Lenape include Dizzie Gillespie, Billie Holiday and Ray Charles, who briefly lived at 633 West Church Street. Today the building looks worse than it did when it was acquired by the City of Jacksonville decades ago as a part of a failed plan to revitalize the area.