In follow up to the essay below on the Preparatory School, let me say a little more that I have recently learned about the subsequent school for former slaves that stood a block to the south at the NE corner of Rosemary and Henderson Streets. Battle provides some more information about the matter in his Sketch of the Life of Wilson Caldwell (1895), but first let me explain (in case you don't know) who Wilson Caldwell was.
UNC Pres. Joseph Caldwell had a slave named November Caldwell who was highly regarded by the Chapel Hill community (as highly regarded as slaves could be said to have been). November's son Wilson was born a slave in 1841. Wilson's mother was a slave of David Swain, so he was given the name Wilson Swain at birth, but after emancipation Wilson went by Wilson Swain Cladwell. Wilson was also very highly thought of in Chapel Hill. He was appointed Justice of the Peace by Reconstruction Governor W. W. Holden. Wilson was also elected to the Chapel Hill Board of Commissioners in the 1880's (the third African American to serve on the Chapel Hill board). Wilson's descendants still live in this area and many of them have dedicated their lives to public service, particularly in the area of law enforcement.
So, here's the tie in with the school, Battle relates in his sketch: "This position [waiter at the University] he held until the beginning of 1869, when he resigned in disgust at the cutting down of his wages so low as not to be sufficient for a decent support in the style to which he had been accustomed . . . Caldwell, after throwing up his post in the University, applied for and obtained from Mr. Samuel Hughes, County Superintendent of Public Schools, a license to take charge of a free school for colored children in Chapel Hill at $17.50 per month . . . In his church relations, he differs from the most of his race at Chapel Hill. He is a memebr of the Congregational Church, which for several years has been supporting a school for the colored in the old Methodist church, bought when the Methodists moved into their larger more beautfiul building on Franklin (or main) street."
So it appears that Wilson Caldwell was the teacher/principal of the school house at the corner of Henderson and Rosemary. And based on the timing, it sounds as though he may have been the first teacher/principal of that school.
Also it seems clear that Wilson Caldwell's school was in the exact same building that had been the Methodist Church. The website of University UMC Church states: "In 1850, Samuel Milton Frost, a university student, served as minister. Determined to carry out Deems’ plan to build a church, Frost traveled the state and raised $5,000 for a church building. The church — dedicated in 1853 — still stands on Rosemary Street."
Battle's History also relates: "he joined the Congregational Church. This denomination did not flourish in Chapel Hill. Soon after Caldwell's death [in 1898] its authorities sold their church building and schoolhouse and left the village."
So here is the approximate chronology of the corner of Henderson and Rosemary Streets:
1853 Methodists build church
1868 Methodists buy new lot on Franklin Street
1869 Congregationalists open school for African Americans
1898 Congregationalists sell school building