After the United States took control of Florida and American discriminatory laws threatened the multi-racial Kingsley family, most of them moved to Haiti. Kingsley died soon after, and Anna returned to Florida to dispute her husband's relatives' contesting Kingsley's will; they sought to exclude Anna and her children from their inheritance. The court honored a treaty between the United States and Spain, and Anna was successful in the court case, despite a political climate hostile toward blacks. She settled in the Arlington neighborhood of Jacksonville, where she died in 1870 at 77 years old. The National Park Service protects Kingsley Plantation, where Anna and Kingsley lived on Fort George Island, as part of the Timucuan Ecological and Historic Preserve.
Daniel L. Schafer, the biographer of Anna Kingsley, has based his account of her early life on conjecture given his research into the history of the area. She was born Anta Majigueen Ndiaye in 1793 in present-day Senegal, in a portion of West Africa that was rent by a fierce war between the majority Wolof people and the minority Fula. Slave raids were frequent occurrences during incessant violence that left many small villages deserted, as people were abducted to be sold into slavery or they fled in fear for their lives. Following an intensifying of the crisis in 1790, Anta was captured in 1806 when she was about 13 years old, probably by Tyeddo raiders from the Futa Toro. Wolof tradition holds that a mythological figure named Njaajaan Ndiaye established the Jolof Kingdom that existed between 1200 and 1550. Through her father, Anta was a Ndiaye descendant and carried that name. Her mother also had ancestors who had held the title of the Buurba Jolof, or king of the Wolofs. Although lineages are disputed, there is a belief that Anta may have been the daughter of a still ruling (as opposed to formerly ruling) branch of the royal family.
Schafer suggests that Anta may have been sent to Gorée Island, a slave debarkation point from the West African coast to the Americas. She sailed to Havana, Cuba; the name of the ship she was aboard is unknown. When Africans arrived in the Western Hemisphere to be sold into slavery, slave traders did not record their given names, but only their age, sex, and sometimes ethnicity, which were most important to buyers. In September or October 1806, Anta was displayed for sale and bought by a slave trader, merchant, and resident of Spanish Florida named Zephaniah Kingsley, who was 30 years older than she.
After a brief stop in St. Augustine, Zephaniah Kingsley's ship made its way up the St. Johns River, stopping in an inlet now named Doctors Lake. Attached to the lake was a dock, the main entrance to Kingsley's plantation which he had named Laurel Grove. Kingsley had become a citizen of Spanish Florida in 1803, likely because it allowed him to continue his international slave trading, at a time when Great Britain and the United States were moving to prohibit it (which they did in 1807). He had been granted the plantation three years before by the Spanish colonial government in exchange for his having brought 74 slaves to the territory. Spain was making generous land grants to attract settlers into Florida. Many years later, Kingsley wrote that he and Anta, now called Anna, had been married in a traditional African ceremony "in a foreign land", which historians have taken to mean Cuba. By the time she arrived at Laurel Grove, she was pregnant.
Laurel Grove was a prosperous plantation that grew oranges, sea island cotton, peas, and potatoes. Over a hundred slaves were gathered there from multiple African ethnic groups; they lived in two groups of houses. Anna, however, lived with Kingsley in his house. At Laurel Grove, as at many other southeastern plantations, Kingsley used the task system to manage work. Slaves were given a quota to fill; when they were finished, they were allowed to pursue other tasks. Some tended personal gardens, while others produced crafts, both of which they were able to sell. Whether due to cultivation techniques or the task system, Laurel Grove was quite successful. One year the plantation made $10,000, which was an extraordinary income at the time, particularly for sparsely populated Florida.
In 1811, Kingsley granted Anna legal emancipation, which confirmed her high status at the plantation. Most visitors had assumed she was already a free woman. Legal emancipation was critical to her future. Three children had been born to the Kingsleys by this time: George, born June 1807; Martha, born July 1809; and Mary, born February 1811. Kingsley assured their emancipation as well. Had he died before they were freed, Anna and the children would have been sold. As Kingsley was involved in shipping as well as the slave trade, he was frequently away from the plantation. Laurel Grove had a manager, also a slave who had been freed. Kingsley trusted Anna to represent him at the plantation. Much later, Kingsley described his wife as "a fine, tall figure, black as jet, but very handsome. She was very capable, and could carry on all the affairs of the plantation in my absence as well as I could myself. She was affectionate and faithful, and I could trust her." In 1813 as a free woman, Anna Kingsley petitioned the Spanish government for land. She was awarded 5 acres (20,000 m2) in Mandarin across the river from Laurel Grove. She purchased goods and livestock to get her farm started, as well as 12 slaves. Slavery within African societies was a custom with which Anna would probably have been familiar, including the fact that female slaves often married their masters in order to obtain freedom.
Kingsley was kidnapped the same year and held until he endorsed the Patriot Rebellion, an insurgency by Americans to annex Florida to the United States. Americans and American-supplied Creek Indians raided towns and plantations in north Florida, sending any blacks they captured into slavery, regardless of their legal status. The Patriots took Laurel Grove and 41 of its slaves, using the facilities as its headquarters while it carried out similar raids in the area. Kingsley fled after being released, his whereabouts unknown. To evade the Americans, Anna approached the Spanish and negotiated her escape, bringing along her children and a dozen slaves. She burned Kingsley's plantation to the ground while the Spanish watched. Anna asked the Spanish to return her to her own homestead, and she burned it, too, preventing its use by the Patriots. For her actions, after the war the Spanish government granted Anna 350 acres (1.4 km2).
Kingsley purchased another plantation on Fort George Island, near the mouth of the St. Johns River in 1814. The owner's house had been looted and vandalized, but every other structure on the property was destroyed. While the slave quarters and various other buildings were being constructed, Anna moved in between Fernandina and Fort George Island, taking over managing the plantation while Kingsley was away on business. At some point in the 1820s, they built a separate kitchen connected to the main house by a covered walkway. It had a room above it where Anna lived with her children. Called the "Ma'am Anna House", this followed the common West African custom of wives' living separately from their husbands, particularly in polygamous marriages. Kingsley took three other wives, all slaves, while at Fort George Island. Two of them brought children.
Thirty-two slave cabins were constructed not far from Kingsley's house. They were constructed of tabby, made by pounding oyster shells into lime and adding water and sand. The shells came from the massive middens left by the Timucua who previously inhabited the island. Anthropologists suggest that Anna may have had the knowledge to instruct her slaves how to form the tabby because it was widely used in West Africa. The foundation of "Ma'am Anna House" was also constructed of tabby, which proved to be fireproof and more durable than wood. The slave quarters were arranged in a semi-circular pattern that was an anomaly in the South. Some historians have suggested Kingsley arranged them to keep better watch over his slaves. Author Daniel Schafer hypothesized that Anna may have been responsible for the layout of the slave quarters: many African villages were similarly arranged in circular patterns.
In 1824, Anna bore her fourth son John, who was baptized in a Catholic ceremony with the daughter of another of Kingsley's wives. Anna befriended a white woman named Susan L'Engle who was much impressed with Anna, and called her "the African princess". (L'Engle's great-granddaughter, children's author Madeleine L'Engle, wrote of her stories in a book entitled Summer of the Great Grandmother.) Susan L'Engle had the impression that Anna was quite lonely though her jobs at the plantation kept her constantly busy. Kingsley's young niece remembered much later her first impression of Anna:
I remember her very distinctly. She was not black, and had the most beautiful features you ever saw. She was a most imposing and very handsome woman. Her smooth, light brown skin, her dark-eyes and wavy [sic] made her outstanding, and I would not keep my eyes away for admiration. She was quiet and moved with regal dignity—I have never seen anything like her, before or since. Her daughter was there also, and she was very light in color, but not as good-looking as her mother. I was six or seven years old at the time. I was Kingsley’s niece. The next morning my aunt, Mrs. Gibbs, sent two servants for us with a horse and buggy, and we were carried over to Newcastle. My mother was furious that we had spent the night at Ma’m Anna’s, but it could not be helped.
After Spain ceded control of Florida to the U.S. in 1822, the new state government progressively enacted stricter ordinances separating the races, as was common among other states in the US South. Southern states increased restrictions against free blacks after the Nat Turner Rebellion of 1831. The mixed-race Kingsley family was directly and negatively affected by these "illiberal and inequitable laws", as Kingsley stated in his will. Kingsley transferred all their holdings to the three older children and moved to Haiti in 1835. Their two oldest daughters had already married white planters in Florida and remained there. Anna and their youngest son followed Kingsley to Haiti in 1838. In all, 60 slaves, family members, and freed employees moved with Kingsley to Haiti to start a plantation called Mayorasgo de Koka. Because slavery was prohibited in Haiti, Kingsley converted his slaves to indentured servants, who could earn their freedom with another nine years of labor. Kingsley portrayed life in Haiti as idyllic. In 1843, when Anna was 50 years old, Kingsley died on his way to New York, where he was buried.
One of the laws passed by the Territorial Council of Florida that so alarmed Kingsley was the provision that mixed race children could not inherit property. The territory did not recognize interracial or polygamous marriages as legal. The year following Kingsley's death, his sister Martha and her children contested his will as "defective and invalid". Kingsley's sister cited Florida law that forbade black people from owning property, and claimed that Anna and Kingsley's other wives moved to Haiti spontaneously, abandoning the property in Florida to become free people. Anna returned to Florida in 1846 to participate in the Kingsley estate defense, despite the increasingly tense racial climate in Duval County. The court upheld the treaty signed between the U.S. and Spain stipulating that all free blacks born before 1822 in Florida enjoyed the same legal privileges as they had when Spain controlled East Florida. Anna furthermore asked for and was granted the transfer of ownership of slaves who had been sent to the San Jose plantation when the family had moved to Haiti. Her request to rent slaves to other plantations to maximize her profits was rejected by the courts.
Anna and her children became Union sympathizers when the American Civil War broke out the following year. She and other free blacks were evacuated by Union forces when they captured Jacksonville in 1862. She returned home the following year to be closer to her daughters, and died in 1870 at the age of 77.