Over the decades this building has been used for various things. Starting its life as a bank, it has been a feed store, thrift shop, restaurant, grocery, and today it holds a bar, cigar bar, workout studio, barber shop, and coffee shop.
Although some reports claim this building was constructed in 1920, those claims are false. It was actually constructed in 1926. At the height of the real estate boom, Longwood founder Edward Henck teamed up with baseball hall-of-famer turned real estate investor Joe Tinker. Tinker was well known for his time as a shortstop for the Chicago Cubs, there he won three World Series between 1906 and 1910. He the first leg of a famous double play combination that was immortalized in a famous poem: “Tinker-to-Evers-to-Chance.”
After his baseball career, Tinker moved to the Orlando area. He owned several landmark buildings around downtown Orlando. Tinker Field (next to the Citrus Bowl) is named after him. He was inducted into the Baseball Hall of Fame in 1946.
The north end of the building, with its angled front facing the intersection, was the location of the Longwood State Bank. This was the first bank in Longwood, which was a really big deal at the time. However, the bank didn’t last long. It went under like so many others during the Great Depression, closing its doors for good in 1932.
The construction of this building helped mark a turning point in the commercial focus of the city. Previously the business epicenter was Warren Avenue and the railroad. However, what is now Highway 427 (Ronald Reagan Boulevard) was then the Old Dixie Highway (new Dixie Highway was 17-92). With the increasing importance of automobile traffic, this became the main thoroughfare during the Boom Years. The road was an artery connecting Sanford with Orlando and brought in a lot of out-of-town passersby. Coupled with the bank’s importance to the surrounding area, this building represented the keynote location and the new center of downtown.
Today the section that was the bank is occupied by the lively Historic Bar. Inside the pub uses what used to be the bank vault as a storage closest for liquor and random supplies. The two-foot thick concrete walls betray its one-time purpose.
According to the bar owners, they discovered a mysterious basement while doing construction. The entrance or purpose has not been found, but pilot holes were drilled through the cement floor and a camera was lowered down and it looks like a sizable cavern!
In 2018 it was known as Connolly’s Irish Pub. In a well-publicized incident, the former owner barricaded himself inside the pub for a tense standoff with police. Bullet holes dotted the north side windows (facing Church Ave) for quite a while after.
The south half of the building is subdivided into four separate stores. In the early days, those tenants included MacReynolds Drug Store, Jackson’s Grocery, and a barbershop. In the 1980s and 1990s much of it was consolidated into Longwood Glass. From 2000-2020 era, it housed businesses like Zanzabar Coffee, Peddle’s Flower Shop, and an art studio (which since moved to the nearby historic Le Rue House). Presently, it houses Back to Basics Barber Shop, Historic Cigars, Claro’s Coffee (formerly Two Bells Coffee House), and the Box Flow Grow gym.