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Woodlawn Plantation

Woodlawn Plantation was a large forced-labor agricultural estate established by Thomas Peter Chaires in eastern Leon County, Florida.

Last updated August 26, 2026

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Overview

Woodlawn Plantation was a large agricultural estate in eastern Leon County, Florida, located on St. Augustine Road immediately south of the community of Chaires. It was established by Thomas Peter Chaires during Florida's territorial period, which lasted from 1821 until statehood in 1845. The plantation formed part of a wider group of large estates created by the Chaires family in the region. Thomas Peter Chaires established Woodlawn Plantation with his brothers Green H. Chaires and Benjamin Chaires also developing substantial plantations nearby. Green Chaires founded Evergreen Hills Plantation, while Benjamin Chaires founded Verdura Plantation. Together, these estates contributed to the development of the community of Chaires and helped make the area a local agricultural and social center. Woodlawn operated as a forced-labor farm within the antebellum plantation system. Available reference material identifies the estate as large, but the surviving summary of the 1860 Leon County agricultural census does not provide usable figures for its acreage, monetary value, machinery, livestock, enslaved population, corn production, or cotton production. Those omissions mean that the scale and economic output of the property cannot be quantified reliably from the cited material. The plantation's historical importance is tied less to a surviving consumer brand or commercial product line than to its role in the settlement and agricultural history of eastern Leon County. Its association with the Chaires family places it within the broader territorial-era expansion of plantation agriculture in Florida and within the social history of slavery and coerced labor in the region. Woodlawn and the neighboring plantations eventually helped create the community hub of Chaires. In 2000, Chaires was added to the National Register of Historic Places. The available source does not establish whether the original Woodlawn buildings survive, whether the property remains identifiable as a distinct estate, or whether it has a current institutional owner. Accordingly, its present physical and administrative status remains uncertain.

History

Woodlawn Plantation was established by Thomas Peter Chaires on St. Augustine Road in what is now eastern Leon County, Florida. Its creation took place during the Florida Territorial Period, between the territory's organization in 1821 and statehood in 1845. The estate was a large forced-labor farm and formed part of the plantation landscape that developed around the Chaires family in the antebellum period. Thomas Peter Chaires was one of three brothers associated with major plantations in the area. His brother Green H. Chaires established Evergreen Hills Plantation, and his brother Benjamin Chaires established Verdura Plantation. These estates were geographically and socially connected and ultimately helped shape the community of Chaires. The family’s regional prominence also reflected the broader settlement and land-development patterns of territorial Florida. Woodlawn's agricultural operations depended on enslaved labor, as did many large plantations in the antebellum South. The cited account identifies the property as a forced-labor farm but does not provide a documented narrative of the people enslaved there, the management structure, or the crops cultivated over time. The Leon County agricultural census for 1860 is referenced, yet the available record summary leaves the principal statistical fields blank, including improved and unimproved acreage, plantation value, machinery value, livestock value, number of enslaved people, corn production, and cotton production. The estates associated with the Chaires family eventually made the surrounding settlement a community hub. The area retained historical significance into the modern period, and the community of Chaires was listed on the National Register of Historic Places in 2000. That designation recognizes the historical character of the community, although the cited material does not state that Woodlawn Plantation itself received a separate listing. The available sources do not establish an exact construction date, the later disposition of the property, the survival of plantation structures, or the identity of any current owner. Woodlawn is therefore best understood as a documented historical plantation estate rather than an active commercial brand or operating agricultural enterprise.

  • 2000

    Chaires placed on the National Register of Historic Places

    [1]

    The community of Chaires, which developed around the plantations in the area, was listed on the National Register of Historic Places.

  • 1860

    Agricultural census reference

    [1]

    The Leon County agricultural census recorded Woodlawn Plantation, but the cited summary does not preserve usable values for its land, assets, labor force, or crop output.

  • 1845

    Florida statehood

    [1]

    Florida became a state. Thomas Peter Chaires is also identified in the reference material as a voter in the First Florida Election of 1845.

  • 1821

    Beginning of Florida's territorial period

    [1]

    Florida entered the territorial period during which Thomas Peter Chaires and his brothers established large plantations in the region.

Products and positioning

A historically significant antebellum plantation estate associated with the Chaires family, territorial-era agricultural development, and the history of forced labor in eastern Leon County.

Sources1 sources

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