Winston bought lot 14 of block 5 (the corner of McBeal and Leech Streets), lot 5 of block 6 (Smith Street), lot 12 of block 7 (Leech Street), and lot 12 of block 9 (Goodrich Street) in St. Paul; lots 8 through 10 of block 181 (Myrtle Street), lots 4 through 6 of block 194 (Elm Street), lots 1 through 3 of block 156 (Cedar Street), lot 9 (Minnesota Avenue), and lots 7 through 9 (Walnut Street) in St. Peter; lot 9 of block 12 (corner of Franklin and Pearl Streets), lots 1 and 2 of block 27 (corner of Fort and Walnut Streets, Chestnut Street), lot 6 of block 28 (Fort Street), lot 7 of block 30 (corner of Franklin Street), lot 4 of block 31, and lot 4 of block 35 in Hennepin County; lot 3 of section 31 in Township 27 of Range 24 in Scott County; the northeastern quarter of the southeastern quarter of section 30 in Township 32 (north of Range 23, west) in Anoka County; lot 4 of block 32, and lots 9 and 10 of block 49 in Blue Earth County; and “Town of Centralia, about 80 acres & $3 per acre” in Le Seur County.

He was an investor in St. Paul (now Travelers) Insurance, and he lived in St. Paul seasonally from 1855 to 1859. In 1856 he became one of the owners of a charter for the town of St. Peter. Before 1855 he lived in New Orleans, Louisiana. In 1850 his male slaves were ages 40, 38, 28, 26, 18, 5, 3; his female slaves were ages 39, 24 (2 of them), 21, and 7.

Frances: a 22-year-old put up by Winston for sale with her two-year-old daughter in New Orleans in 1854.

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