He was the youngest son of General James Winchester and Susan Black. Attended the University of Nashville and graduated in 1840. He was elected to the state legislature and upon his second offer of re-election he decined.
Civil War Service: Confederate States
Major and A.A.A.G and Quartermaster, served under various individuals: D.S. Donelson, W.G.M. Davis, D.H. Maury, W.S. Bates
Appointed July 21 1862 by Gen. Donelson.
Captured at Missionary Ridge Nov 25 1863, sent to Johnson's Island with his son Napoleon Winchester. While in prison, his mother died in Dec 1864. Released on July 25 1865 on Oath of Parole. After the Civil War he was forced to sell Cragfont, his ancestral home, and he moved to Memphis. His brother, Marcus B. Winchester, was the first Mayor of Memphis. In 1871 Memphis City Directory shows him to be an attorney residing at Valentine Av. near Raleigh Rd. By 1877 was a partner in the law office of Winchester & Winchester at 39 Madison Ave. with his son Thomas Pendleton Winchester. Resided at 317 Madison Ave. According to newspaper reports he was sick for a month prior to his death.

Memphis Daily Appeal
December 31 1878
Died at his residence on McLemore avenue, on Monday morning, December 30 1878 at one o'clock, after a protracted illness, Major George W. Winchester, in the fifty-seventh year of his age. The friends and acquaintances of the family are respectfully invited to attend the funeral services from the First Methodist church, corner Poplar and Second streets, at one o'clcok this Tuesday afternoon. Carriages in attendance.

Married Malvina Henderson Gaines March 9 1841 in Davidson County TN.
Wife:Malvina Henderson Gaines
1821 – 1887
Children:
Alice Lorraine Winchester (married R. J. Person Jan 30 1868 Shelby County TN)
1841 – 1925

Napoleon B Winchester
1843 – 1871

George Washington Winchester Jr, attended University of Virginia.
1846 – 1886

Lucy Leonora Winchester (Most likely interred at Cragfont Cemetery)
1848 – 1854

Thomas Pendleton Winchester (Married Nanna Thurman Feb 11 1874 Albemarle Co. Virginia. Appears in 1900 Census with wife Nanna, age 47 and daughter Agnes age 12. 1910 Census lists wife Leona/Nanna age 56 and daughter Agnes 22.)
1849 – 1920

Susan Black Winchester (married William Davis Powell Apr 12 1877 Shelby County TN. Second husband Dabney Minor Scales)
1852 – 1910

Malvina Henderson Winchester (married William Edwin Wilson Sr Feb 17 1885)
1860 – 1910

Virginia (Birdie) Lee Winchester
1862 – 1877