The Gentry Building faces Gentry Street. It currently consists of three stories of apartments over a half-basement empty business space. It is owned by Olympus Properties. The southwest corner of this building has dropped a great deal in the past 20 years. One possible reason for this was the huge brick oven on the second floor from the days when it was Bloomington's first bakery, according to the historical marker that was on the front of the College Avenue side of this building. Removing this oven slowed the sinking of the southwest corner, by lightening the structure significantly.
According to the American Contractor, December 13, 1913, this building was built by George Benckart and designed by Nichols & Nichols. The general contractor was J. O. White. The March 14, 1914 edition reported that the foundation was complete, but construction had ceased during the winter. The general contractor was seeking bids for the electrical sub-contract and work was to begin again soon.