I had some time last night to transcribe a few entries from Brooklyn City Directories between 1856 and 1869. I have two ancestors who ended up there in the mid to late 1800s. It didn’t help me much but maybe someone else will find this useful. I found the directories at the Brooklyn Public Library by way of archive.org
Searched surname WINN and picked up WINNE, WYNN and WYNNE in proximity to the results.
Smith’s Brooklyn Directory for the year ending May 1, 1856
(Eastern District)
Winn James, carpenter, h. 14th st. n. 3d av.
Winn Thomas, butcher, 34 Hamilton mkt. h. r. 7 Carroll
(Western District)
Winn Eleanor, wid. William, h. 241 S. Fourth
Winn John, laborer, h. 9 S. Fifth
Smith’s Brooklyn Directory for the year ending May 1, 1857
(Eastern District)
Winn William, ropemaker, 97 MoKibbin
(Western District)
Winn James, laborer, Underhill n. Wyckoff
Winn Thomas, butcher, r. 13 Carroll
Winn Thomas, stone cutter, 65 Degraw
Wynn Robert, laborer. Kelsey’s al
Wynne Thomas, butcher, 34 Hamilton market, h r. 13 Carroll
Brooklyn City Directory, for the year ending May 1, 1858
Winn Eleanor, wid. h. 241 S. 4th
Winn James, laborer, h. Underhill av. n. Bergen
Winne T. V. clerk, h. 80 Hoyt
Wynn Jacob, tailor, h. Ewen c. Wyckoff
Wynne Thomas, butcher, Hamilton av. mkt. h. 52 President
Brooklyn City Directory for the year ending May 1, 1862
Winn James, laborer, h. 14 Hudson
Winn James, lather, h. Underhill . n. Bergen
Winn James, liquors, E. Warren c. Hoyt
Winn John J. seaman, h. 42 John
Winn Thomas, laborer, h. 6th n. N. 5th
Winne Donald D. salesman, h. 102 S. 9th
Wynne Patrick, butcher, 558 Columbia
Wynne Thomas, butcher, 558 Columbia
Brooklyn City Directory for the year ending May 1, 1863
Winn James, grocer, E. Warren c. Hoyt, h. 94 E. Warren
Winn James, lab. h. Underhill av. n. Bergen
Winn Robert, porter, h. Kelsey’s al. n. Columbia
Winne Daniel D. com. mer. 26 Cortlandt, N.Y. h. 16 S. 4th
Winne Fisher, stoves, h. 94 Duffield
Winne George, stonecutter, h. 177 Taylor
Winne Mary, wid. cook, h. 330 2d
Winne Patrick, laborer, h. r. 50 Raymond
Wynn William & Co. druggist, 150 Fulton av. h. 250 Schermerhorn
Wynne James, grocer, E. Warren c. Hoyt
Wynne Patrick, J. butcher, Court c. 4th pl. h. 558 Columbia
Brooklyn City Directory for the year ending May 1, 1864
Winn James, laborer, h. 20 Hudson av
Winn James, laborer, h. Underhill av.n. Bergen
Winn James, liquors, 94 E. Warren
Winn John, laborer, h. Greene c. Union av
Winn John J. watchman, John n. Gold
Winn Mary, wid. h. 830 2d
Winne D. D. com. mer. h. 16 S. 4th
Wynn Patrick, butcher, Court c. 4th pl
Wynne William & Co. druggists, 150 Fulton av. h. 97 State
Brooklyn City Directory for the year ending May 1, 1865
Winn James, grocer, 94 E. Warren
Winn James, butcher, h. Underhill av. n. Bergen
Winn James, seaman, h. 168 York
Winn John J. laborer, h. B’way. n. Myrtle av
Winne Hiram P. sash & blinds, h. 229 5th
Winne James, machinist, h. 9 17th
Winne Samuel, h. 244 1st
Wynn William & Co. druggists, 15 Fulton av. h. 102 Fulton av
Wynne Patrick, butcher, Court c. 4th pl
Wynne Thomas, butcher, 557 Columbia
Brooklyn City Directory for the year ending May 1, 1866
Winn Elcia, (col.) seamstress, h r. 62 Prince
Winn James, grocer, 94 E. Warren
Winn James F. plasterer, h Underhill . n. Dean
Winn John J. watchman, h 138 Prospect
Winn Patrick, clerk, h 147 Jay
Winn Samuel, seaman, h 28 N. 2d
Winn Thomas, b Nelson n. Hicks
Winne Daniel, h 41 S. 4th
Wynn William & Co.drugs, Bond, c. Fulton . h 1 Bond
Brooklyn City Directory for the year ending May 1, 1867
Winn John, porter, h 64 Butler
Winn May, wid. h 330 2d
Winn Patrick, porter, h 147 Jay
Winn Samuel, auctioneer, h 28 N. 2d
Winn William, peddler, h 120 E. Baltic
Winne Daniel D. salesman, h 41 S. 4th
Winne James, porter, h 158 Hudson av
Wynn James, leather, h Underhill av.n.Bergen
Wynn William & Co. drugs, 150 Fulton av
Wynn W. P. engineer, h William n. Richard
Wynne James, butcher, h 557 Columbia
Wynne James, grocer, 94 E. Warren
Wynne James, lab. h 168 York
Wynne Patrick J. police, h 557 Columbia
Wynne Thomas, mkt. 557 Columbia
Brooklyn City Directory for the year ending May 1, 1868
Winn Bernard, upholsterer, h r. 22 High
Winn George, tailor, 114 Smith
Winn James, grocer, 94 E. Warren
Winn James, lab. h 20 Hudson av
Winn John, lab. h 12 Union pl
Winn Mary, wid. laundress, h 12 Union pl
Winn Michael, lab. h Schenck n. Myrtle av
Winn Patrick, h 147 Jay
Winn Patrick, lab. h Lafayette av. n. Classon av
Winn Thomas, lab. h 12 Union pl
Winn William, drugs, h 174 Dean
Winne James, h 158 Hudson av
Winne John, cabinetmkr. h 250 Union av
Winne Julia E. wid. h 94 S. 8th
Wynn William & Co. drugs, 150 Fulton av, h 174 Dean
Brooklyn City and Business Directory for the year ending May 1, 1869
Winn Andrew, lab. h Lafayette . n. Steuben
Winn James, carman, h 158 Hudson
Winn James, lab. h 20 Hudson
Winn James, leather, h Undehill .n. Bergen
Winn Michael, lab. h E. Warren n. Grand
Winne D. V. clerk, h 41 Elliott pl
Wynn James, grocer, 94 E. Warren
Wynn Patrick, porter, h 94 E. Warren
Wynn William, drags, 150 Fulton . h 2 Elm pl
Wynn & Co. drugs, 150 Fulton
Wynne John P. painter, h 64 Butler
Wynne Margaret, wid. h 83 Union
Wynne. Patrick J. butcher, 39 Carroll, h 83 President
Wynne Terence, junk, 37 President, h 52 President
Wynne Thomas, boarding, 14 4th pl
Wynne Thomas, butcher, 635 Court, h 14 4th pl
Trade Heading: Carmen
Winn James 158 Hudson