A contract signed in 1862 built the first Winona County Courthouse on the southeast corner of Third and Washington, just north of the current building, which replaced it in 1889.
Charles G. Maybury designed the 1889 courthouse in the Richardsonian Romanesque style. The building displays Victorian variety in its two unmatched towers, in the contrast between the Dresbach buff sandstone of its three stories and the Lake Superior brownstone trim, in the cut stone, and in its carvings.
The county started a sinking fund for this building in 1882. It was completed in 1889 at a cost of $120,000. James A. Tawney, a Winona attorney later elected to Congress and Chairman of the Ways & Means Committee, assisted Maybury with plans.
In addition to an architect, the budget allowed for walls of solid brick and stone, wood joists and iron lath in floors, plus two inches of concrete. It also provided for a galvanized iron cornice, French glass windows with stained glass transoms, black slate for the roof, copper flashings and gutters, terra cotta crestings and finials, and Cleveland blue sandstone steps. The main hall has heavy, carved, red oak woodwork and four- and five-foot wainscoting. Each main room has 16-foot ceilings and a fireplace with carved wood mantels and tile.
In 1970, the Winona County Courthouse became the first Minnesota courthouse to be placed on the National Register of Historic Places. However, its future was uncertain. In February 1971, District Judge Glenn E. Kelley, later a Minnesota Supreme Court Justice, denied a bid to save the building. At the end of the year, $1.1 million in bonds were approved for a controversial remodeling of the courthouse.
A plan was not approved until three years later, however. It called for making five floors where there had been three and retaining and cleaning the exterior. Total remodeling cost $2 million, which was partially paid for by a HUD grant and a Minnesota Resources Commission fund. Another $230,000 was spent in 1981 for roof repairs.
Early one morning in the fall of 2000, the inside of the building was destroyed when a ceiling collapsed and water pipes broke, sending hundreds of gallons of water pouring through the building's hallways, ceilings, and courtrooms. For three years, court operations were conducted in Winona's old middle school and other county offices moved to a former bank building.
The inside of the courthouse was repaired and much of it was restored to its original condition at a cost of $5.6 million. Another $1.5 million in restoration was done to the outside. The building was re-dedicated during a ceremony with the Minnesota Supreme Court and the Third Judicial District bench on Oct. 13, 2003.