Montgomery County is named for Richard Montgomery, who was a United States general killed in the American Revolutionary War.
Surrounding County Courthouses:
N – Grenada County
E – Webster County and Choctaw County
S – Attalia County
W – Carroll County
Created: May 13, 1871 
County Seat:
Winona 1871 – present
County Courthouse – Winona
Location: 618 Summit Street / North Applegate Street
Built: 1974 – 1976
Style: Modern
Architect: McRee, Dardaman and Kennington
Contractor: Central Construction Company
Description: The building faces south and is a one story buff colored brick and concrete structure. The low building is square shaped and is located on spacious landscaped grounds to the west of the center of Winona. The south front has a central recessed section with recessed glass panel entrance. A wide concrete band runs below the flat roof line. There are narrow vertical brick dividers across the front and along the sides where the windows are located. The roof line is flat. The County Circuit Court courtroom is located in the center of the building. The building houses the County Circuit Court of the 5th Judicial District, County Chancery Court and County Youth Court.
See: The 5th Judicial District includes Attalia County, Carroll County, Choctaw County, Grenada County, Webster County and Winston County.
History: The county was created in 1871 and Winona was selected as the county seat. The first courthouse was built after 1871. There was a fire in 1888 which destroyed most of the town center. The second courthouse was a two story structure designed by Bruce Architectural Company and constructed by M T Lewman & Company of Louisville, Kentucky in 1903 to 1904. The third and present courthouse was constructed in 1974 to 1976. The cornerstone for the old courthouse constructed 1903 – 1904, is located on North Quitman Street. The building stood where the Winona – Montgomery County Library stands today. The architect was Bruce Architectural Company and the contractor was M T Lewman & Company of Louisville, Kentucky.
County Courthouse – Winona
County Circuit Court courtroom
Cornerstone 1904 County Courthouse
Picture 1904 County Courthouse
Photos taken 2012, 2017 and 2019