One of the earliest brick structures in Old Webster was the Allen Building, renowned for its impressive size, spanning nearly an entire city block. Constructed by Nathan D. Allen and completed around 1888 on Gore Avenue at the Missouri Pacific Railroad tracks (SW corner), the third floor featured the Allen Music Hall, hosting fine music and theater performances, with special train cars running from St. Louis for the events.

The building accommodated a drug store (Douglas Drug Store), a grocery, a hardware store, a barber shop, and a bakery managed by his son, Harry Allen. The second floor housed offices and a kindergarten school.

Directly to the south on Gore Avenue was Bredall's Meat Market.

Tragically, the building was consumed by a devastating fire on Friday, Febraury 10th, 1899, which posed a threat to all of Old Webster. The bucket brigade, supported by a horse-drawn water wagon from St. Louis, managed to extinguish the flames and saved the day.

Though 81-year-old Nathan D. Allen initially expressed intentions to rebuild, delays in demolishing the remaining walls led to public nuisance complaints, and he ultimately did not reconstruct. The Webster Groves Trust acquired the property and erected a one-story building in 1901.