Wirick-Simmons House

The Jefferson County Courthouse is an historic Classical Revival style courthouse building located in Monticello, Florida. Built in 1909, it was designed by Georgia-born architect Edward Columbus Hosford, who is noted for the courthouses and other buildings that he designed in Florida, Georgia and Texas. The builder was Mutual Construction Company of Louisville, Kentucky, whose bid for the project was $39,412.It was modeled on President Thomas Jefferson’s famous house, Monticello, for which the town is named.The motto, Suum Cuique, Latin for To each his own, which is inscribed over the doors of the courthouse, is jokingly pronounced Sue ‘em quick by some local residents.The building is a contributing property in the Monticello Historic District, which was added to the National Register of Historic Places on August 19, 1977

The Perkins Opera House (also known as the Monticello Opera House) is a historic theatre in Monticello, Florida, United States. It is located at the corner of Washington Street and Jefferson Street.

The Monticello Historic District is a U.S. Historic District (designated as such on August 19, 1977) located in Monticello, Florida. The district includes an irregular area along Madison, Jefferson, Dogwood, and Washington Streets and contains 41 historic buildings. Contributing properties in the district include: Christ Episcopal Church (Monticello, Florida) Jefferson County Courthouse (Florida)

Jefferson County Jail is a national historic site located at 380 West Dogwood Street, Monticello, Florida in Jefferson County. The Masonry Vernacular building was constructed in 1909, with alterations in 1940 and 1960. The design is typical for small jails of the early twentieth century: on the first floor there are the living quarters for the sheriff or deputy and his family, and on the second floor there are the steel cages for the inmates. It was added to the National Register of Historic Places on January 15, 2014.The building is under restoration and is now operated as the Monticello Old Jail Museum by Main Street of Monticello, Florida, Inc.

Monticello ( MON-tiss-EL-oh) is the only city and the county seat of Jefferson County, Florida, United States. The city is named after Monticello, the estate of the county's namesake, Thomas Jefferson, on which the Jefferson County Courthouse was modeled. The population was 2,589 at the 2020 census. Monticello is home to Indian mounds and many historic buildings, including the Perkins Opera House and Monticello Old Jail Museum.

The Denham-Lacy House is a historic Inn located in Monticello, Florida.

The Palmer-Perkins House is a historic home in Monticello, Florida. It is located at 625 West Palmer Mill Road. On July 10, 1979, it was added to the U.S. National Register of Historic Places. On March 18, 1986, there was a boundary increase to this site, also referred to as the Palmer-Perkins House and Palmer Family Graveyard. It extended the listing to 185 West Washington Street.

Jefferson County Middle / High School (JCMHS) is a public school in unincorporated Jefferson County, Florida, with a Monticello postal address. A part of Jefferson County Schools, it serves grades 6 - 12. The school's mascot is a tiger and the school colors are orange and blue. It is at 50 David Road, 4 miles (6.4 km) south of the center of Monticello. The school was formerly housed in the historic Jefferson Academy building, opened in 1852 in the first brick school building in Florida. Minority enrollment at Jefferson County Middle / High School is about 340 and 84 percent minority. It was operated by Somerset Academy Inc. for five years. The student body is minority majority, about 60 percent African American.

The Palmer House is a historic home in Monticello, Florida. It is located at Palmer Mill Road and South Jefferson Street. On November 21, 1978, it was added to the U.S. National Register of Historic Places.

Girardeau House is a national historic site located at 950 East Washington Street, Monticello, Florida in Jefferson County. It was added to the National Register of Historic Places on June 30, 2011.