Built in 1852 by William C. Garretson as an Italianate family home, this Waterloo property passed in 1854 to Martin Schilling, who moved there from Millstadt with his wife, Anna Maria Hoock, and their six children, lived on the first floor, and operated a tavern and dance hall on the second floor. The Schilling family was struck by repeated tragedy: Martin Schilling III died in 1871 at age 23; within the next three years Louis Schilling and his wife Brigit also died, leaving four children adopted by Nicholas Schilling; Anna Marie Schilling died in 1875 at age 56 of winter fever; Martin Sr. was killed in his tavern in December 1878 during a bar fight over a bottle of wine; and one year later Nicholas Schilling was robbed and stabbed to death on his way to St. Louis. After the family sold the property and left Waterloo, it was owned for 36 years by Louis Eilbracht, then by William T. Demint, and then by David M. Hardy, a prominent Monroe County community member who served on the school board and helped organize the Harrisonville Telephone Company and the Commercial State Bank of Waterloo. The property later passed to the Quernheim family, whose furniture and funeral business began with Balthasar Quernheim in Maeystown, Illinois, in 1858 and moved to Waterloo after his death in 1898 under Henry Quernheim Jr.; Hermann Quernheim later ran the business until 1928, after which Emil, Albert, and Arthur Quernheim formed the H. Quernheim Company. After Arthur's death in 1951, Emil and Albert continued until 1969, when Albert sold his share to Emil, who then operated with his sons David and Paul; after Emil died in 1979, David and Paul formed the Quernheim Funeral Home. The family later moved the business to Market Street in 1988 and sold 229 South Main to Larry and Sandra Hurley for residential use; the property then passed to David Kahn in 1992, who used the lower floor as a law office and the upper floor as residential space, and in April 1997 it was sold to Floyd E. Crowder and then to Monroe County Title Co., which remodeled the first and second floors for business use.