William Sherman Jennings House

The Brooksville 1885 Train Depot is one of three museums operated by the Hernando Historical Museum Association. The museum is located just south of downtown Brooksville, Florida on Russell Street. It was originally built by the Florida Southern Railway. The museum is dedicated to the railroad, and local history of Brooksville, Hernando County, and Florida.

Bethlehem Progressive Baptist Church was a historic church founded for African Americans in Brooksville, Florida. It was built in 1861 at 661 South Brooksville Avenue. Fort Taylor Cemetery served the community. The church's historical site is a stop on the Florida Black Heritage Trail. Bethlehem Baptist Church is now at the site.

The Judge Willis Russell House (also known as the Verona House) is a U.S. historic building in Brooksville, Florida. It is located at 201 South Main Street. On January 27, 1999, it was added to the U.S. National Register of Historic Places.

The T.S. Coogler House is a historic residence in Brooksville, Florida that belonged to pioneering educator and lawyer T.S. Coogler (Theodore Sylvestor Coogler). The home later belonged to Judge Monroe Treiman. It is located at 133 South Brooksville Avenue. The Colonial Revival architecture house has two-story columns. It is part of the South Brooksville Avenue Historic District. Brooksville's second courthouse may have been built with lumber from Coogler's mill.

The Frank Saxon House is a historic residence in Brooksville, Florida. The home was built by Frank Saxon in 1864 for his bride Tululu Hope, daughter of William Hope, one of the earliest settlers in the county. Mr. Saxon was a Civil War hero who was a member of the Hernando Wild Cats, a unit of the 3rd Regiment of the Confederate Army. After the war, Frank Saxon served as a member of the Florida Legislature representing Hernando County. The home sits on the top of a hill at 200 South Saxon Avenue. On November 5, 1998, it was added to the U.S. National Register of Historic Places. The Frank Saxon House is one of the earliest examples of Frame Vernacular architecture with Queen Anne Revival influence in Hernando County. The exterior of the home has been renovated by the owners, but the interior is still in need of repair.

Brooksville, a city, is the seat of Hernando County, Florida, in the United States. At the 2010 census it had a population of 7,719, up from 7,264 at the 2000 census. Brooksville is home to historic buildings and residences, including the homes of former Florida governor William Sherman Jennings and football player Jerome Brown. It is part of the Tampa–St. Petersburg–Clearwater, Florida, Metropolitan Statistical Area. Brooksville, established in 1856 by the merger of the towns of Melendez and Pierceville, took its name to honor and show support for Preston Brooks, a pro-slavery congressman from South Carolina, who caned and seriously injured Charles Sumner, an abolitionist and United States senator from Massachusetts.

First National Bank is a historic bank building in Brooksville, Florida. It was built in 1910 and is located at 1 Main Street. The 2-story brick building includes cast iron columns. The brick exterior was remodeled to give it a more Neoclassical appearance before 1926. The bank's first president, John Weeks, owned Weeks Hardware (built in 1913) at 115 North Main. It is now used for the offices of Browning Insurance. John R. Culbreath once served as the chairperson for the bank.

The Hernando County Courthouse, built in 1913, is an historic courthouse building located in Brooksville, Florida, It was designed by Atlanta-based architect William Augustus Edwards who designed one other courthouse in Florida, two in Georgia and nine in South Carolina as well as academic buildings at 12 institutions in Florida, Georgia and South Carolina. He designed most of the original buildings on the campus of the University of Florida in Gainesville.The courthouse been called the Brooksville crown. In 1989, The Hernando County Courthouse was listed in A Guide to Florida's Historic Architecture, published by the University of Florida Press.

The May-Stringer House, home of the Hernando Heritage Museum, is a historic residential building in Brooksville, Florida, United States. It is located at 601 Museum Court. On March 8, 1997, it was added to the National Register of Historic Places. Overlooking the City of Brooksville, the house is a 4-story, seven gable, gingerbread trim, 14 room “Painted Lady” Victorian era home. The Hernando Historical Museum Association has created exhibit rooms with a Victorian Look, and there are rooms devoted to specific themes such as an Elegant Dining Room, Victorian Bedrooms, Military Room, an 1880s Doctor's Office, and a 1900s Communication Room. The museum contains over 10,000 artifacts that can be viewed.

Weeks Hardware is a historic two-story brick 1913 hardware store building in Brooksville, Florida, located at 115 North Main.The store was called Miro Hardware through the end of World War II, as a combination of the first names of Rosie and Mammie Weeks. As of 2003, the store was the "oldest active business in town," according to the St. Petersburg Times, which added: The reluctance to modernize is evident everywhere. The ceiling is high, made of elaborately patterned tin and in need of paint. The freight elevator in the back of the store is powered by hand. A tall, darkly stained plywood case that holds bolts and screws in its dozens of drawers, was built, according to a little brass label on one corner, by A.R. Brown on May 7, 1901. The founder's grandson, Joseph C. Weeks, worked in the store since childhood, and took over the business after returning from naval service and graduating from the University of Florida. Mr. Weeks, aged 82, was honored by the Brooksville City Council as "the 2009 Great Brooksvillian."The building was owned by John Weeks, the first President of the First Federal Bank.The historic J.M. Rogers Department Store built in 1912 is located across the street at 120 North Main.

WWJB (1450 AM, "103.9 The Boot") is an American radio station licensed to serve the community of Brooksville, Florida. The station, established in 1958 as WKTS, is currently owned and operated by Hernando Broadcasting Company, Inc. WWJB is also repeated on FM translators W222CI 92.3 FM Brooksville, Florida and W280DK 103.9 FM Spring Hill, Florida.

Hernando High School is a public high school located in Brooksville, Florida. It is part of the Hernando County School District. It has been in operation since 1889, which makes it one of the oldest continuously operating public high schools in the United States.