Roque Leonardy married Esperanza Valle on Minorca. They settled in New Smyrna and welcomed baby daughters in both 1771 and 1772. Then Esperanza died.
In 1773, Leonardy married another Minorcan colonist, Agueda Coll. She was a widow of a fellow colonist named Juan Castellvell, and had a two year-old son. Leonardy and Coll were together when the Turnbull colony rebelled and the survivors moved to British Saint Augustine. They were quartered for a time in what has been referred to as the Greek settlement. It extended from Hypolita Street to the city gates, from the Cordova area to the bay.
Leonardy rose in five short years to be called Don Roque Leonardi, a lieutenant in the city militia. In the first Spanish census in 1783, Leonardy is listed as a wine merchant of Granella, Italy. Catholic, with a wife, and only three surviving children (Clorinda, Juan, Bartolome). He owned two and a half acres of land with a house, and another house in the city which he inhabited in the Plaza of the Quarters. Leonardy had five slaves.
Leonardy was originally from Castelnuovo di Garfagnana in Tuscany, Italy, a town located at the confluence of the Serchio and Turrite Secca rivers, close to the intersection among the roads passing through the Apennine Mountains and the Apuane Alps.
The house in town was on Charlotte Street on the corner of Bridge Street, west side. In the Spanish Deeds in 1784, Leonardy is listed as purchasing two stone houses on Hospital (now Aviles) Street. These would be today on the corner of Aviles and Bridge, convent backyard. He also purchased the lot and house where the convent kindergarten is today on Saint George Street.
Another full Spanish Census was made in 1787. Leonardy owned four houses, had 12 horses, 50 acres of land, a "hamlet" and shops in the Plaza.
Years later in the Spanish land Grants when the heirs were petitioning for title it states that in Dec. of 1792 the 1st grant was made, another in April 1793, the last in Jan. 1799, giving him full 2000 acres. He planted grapevines and became famous for his vines and his wines. (Spanish Land Grants. Vol. 4, Page 48. L-9).
Another census was taken in 1793. Roque, while in town, was still living on present day Aviles Street Corner of Bridge (Cunningham Lane then). The Census repeated the name of his parents, listed his age as 51. It gave Agueda, her parents and her age as 41. Clorinda was 17 years, a young lady. Juan was fourteen. Bartolome was 9. Jacoma Antonia was six and Margaruete was three. They had a slave in town (evidently to distinguish those from the plantation) and 3 negroes (house servants).
Don Roque was the Ensign of the Militia, appointed one of the valuators of the Fish Estate (on Anastasia today). He had four houses in town and a large wine plantation on the North River.
In 1801, Leonardy was drowned. His sons, Juan and Bartolome carried on the work of the plantation until ordered out during the insurrection of 1812. It was stated later that Juan served from “call to arms” during that insurrection and petitioned for 160 acres of his own after it.