Monticello Historic District, Historic district in Monticello, Florida, US.

Monticello Historic District is a protected area in Florida containing 41 historic buildings distributed across several main streets. The structures span different eras and show how this town developed over time.

The area received National Register of Historic Places recognition in 1977, protecting buildings that began appearing from 1828 onward. These structures document nearly a century of building styles and urban growth.

The district displays a mix of architectural styles ranging from classical revivals to Victorian designs that shape how the streets look and feel. This blend of periods creates a varied visual experience as you walk through the neighborhoods.

You can explore the area on foot, walking through several streets lined with historic buildings. A good starting point is the Wirick-Simmons House, where the Jefferson County Historical Association displays local objects and documents.

The district's 41 contributing buildings include the Perkins Opera House and the Wirick-Simmons House alongside the Jefferson County Courthouse and Christ Episcopal Church. The district boundary follows an irregular stretch of Madison, Jefferson, Dogwood and Washington Streets rather than a neat grid.