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The Historical Buildings

  • Writer: Old Brooksville
    Old Brooksville
  • Nov 14, 2025
  • 4 min read

Updated: Feb 12


Building the Hernando State Bank (1905). The first bank in Brooksville since 1897. The Brooksville State Bank opened in 1890, but the citrus freeze drove them under.


These are the buildings that have stood the test of time and are one of the best reminders of our past and how it must have been for local citizens living here over 100 years ago.


Considering that our local history as an American experience dates back to only about 1835-40, in the scheme of things and compared to the rest of the world, our history is relatively short.


The oldest of these buildings featured in this issue date back to 1884. Most were build in the 20th century. These early buildings that helped shape the face of the city are now long gone yet their contributions live on in shaping the character of the city.



Thanks to the following for their contributions


John White

George Allen Jr.

Hernando Historical Society

Florida Archives




The oldest building still standing is the Brooksville Methodist Church. Built during 1891-92, it has been expanded and revised over the years but still stands recognizably unique. This 1907 photo has a quiet, still charm to it.



The new First National Bank (1908) at the corner of Broad and Main. This would evolve into today's King Insurance (Browning) Building.



The Jennings Building (1905) at the corner of Main and Broad was built around 1900. In 1914 a fire wiped out the entire block and the Jennings was rebuilt in 1915. To the left is A.N. Chelf's Drug Store which was here until 1930 and then morphed into Murphy's Drug Store, then Hogan's in 1955. To the right is Jennings Merchandise, later known as the Florida Cafe, a popular restaurant with tourists during the 1940s and 50s.




The brand new Hernando County Courthouse (1913). This replaced the old courthouse which was built in 1878. By 1913 the old frame structure was termite ridden and in poor condition. This was at the same time all the streets near the courthouse were paved. Some streets were paved with bricks and are still in use today.




Newly discovered photo shows Brooksville, February 1922 during Tourist Day. By then the automobile was king and the horse and carriage a thing of the past.




Hernando State Bank (left in 1913). Down the street is the famed but doomed Varnada Hotel. The bank building still stands as the Truist Bank. Next door was Coogler's Drugs, in business since the 19th century. Today all are gone except the bank.




Businessman's lunch (1925). A large group dines at the Tamiami Cafe at the corner of Main and Jefferson. This is the Jefferson side where Main Street Eatery is today.




The new St. Anthony's Catholic Church (1908) on Olive Street. It served here until the late 1960s. It is now a private residence.




The new Hernando High (1925) on Bell Avenue. It would serve students until early 1960 when they moved to the current school. Today, it is a Baptist school and church record facility.




Brooksville Orange Packing Plant (1925) on what is now MLK Blvd. This was just east of South Main Street.




Main Street (1925). To the left is the Tamiami Cafe. which began here in 1923. In 1936, the Tamiami moved to Broad Street. The spot here was then replaced by Bacon's Drug Store, which was down the street on the left. In 1928, a fire destroyed the third floor. Today, the two-story building features the popular Main Street Eatery.




The new Tangerine Hotel (1926) on Howell Avenue. For many years, the Tangerine was the place to be seen as it featured fine dining and live entertainment. Dignitaries, entertainers, inventors and noted businessmen all stayed here through the 1940s. In 1931, a famous bootleg murder occurred here. Today it is a retirement facility.




The First National Bank (1926) on the corner of Main and Broad, would later evolve to become the Brooksville Post Office during the 1940s, then Mcethan Browning in the 1950s, then becoming Browning Insurance. It is now King Insurance.




This quaint little cottage was one of Brooksville's earliest libraries in 1926, the Bookshop of the Tamiami Trail. It was at the home owned by Mr. and Mrs. Ashbrook. The cottage would later become the main entrance to the enchanting Rogers' Christmas House (1972-2010) which at one time at its peak had six houses, each one with a theme superbly done by Margaret Weenie Rogers, who put Brooksville on the world map, drawing tourists to get to the closest thing to that childhood Chrismas feeling you once had.




West Coast Lumber Co. (1927) was on South Main Street. The building still stands.




January 1941, corner of Broad and Jefferson looking toward Bacon's Drug Store. The building was built shortly after a devastating fire in 1917 that wiped out the entire block. The Tamiami Cafe occupied it from 1923 to 1936 when Bacon's Drug Store moved in from the west corner of Ft. Dade and N. Main. The very popular Bacon's Drug Store was a favorite with tourists as well and continued to operate from this location until the early 1970s. Today it is Main Street Eatery.




1933 Maillis Grocery ad


The Maillis Grocery was inside the Jennings Building from 1923 through the 1960s. During the Depression, even these low prices were out of reach for many.





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