The space currently occupied by the Eõ Inn and Persimmon Brewing has served many uses over the years. Built in 1922, it was originally named the Eola Hotel. Later called the Bonnie Villa Hotel, it was sold in 1925 and developed into a modern clinic with 11 doctors. In 1932, the building became a college of music. From 1954 the YMCA occupied the space for its headquarters. Later years would also include time as a retirement home, a youth hostel, boutique hotel and restaurant.
The space currently occupied by the Paramount originally belonged to O.P. Swope, the founder of the First Federal Savings and Loan Association.
The space currently occupied by Eola Wine Company, at the intersection of East Central Boulevard and South Osceola Avenue, formerly housed another Colonial Revival-style house built in 1915. This was the home of dentist Alton B. Whitman, who would be the president and founder of the Orange County Dental Society. His wife, Helen, would become the first woman to act as an election teller in Orlando.
In 1917, James L. Dean, built a home at 614 East Washington Street. He founded the City Drug Store in 1914, staying open until 1922.
The space currently occupied by the UPS store on East Central Boulevard was the former site of the Cook House. John M. Cook, Orlando's first auto mechanic and car salesman, built his home in this location in 1917. He also had a blacksmith shop nearby on East Pine Street. His Colonial Revival-style house was torn down in 1988.
In 1938, Nobel Peace Prize winner John Raleigh Mott bought a bungalow on the land that is now part of Lake Eola Park, originally built in 1920. The house was demolished in 2013 as part of the Lake Eola Park expansion.
Eola Drive, home to the Eola Square group of businesses, was formerly named East Street as a nod to it being Summerlin’s Easternmost property boundary. It was changed to Eola Drive in 1923.
While luxury townhomes may be commonplace in downtown Orlando now, built in 1969, the Summerwinds Townhomes became one of the earliest examples of the architecture in the downtown Orlando core.
In 1985, the 530 East Central condominium was built. This would become one of, if not the first high-rise residential buildings in Orlando’s downtown core.
Other major developments in South Eola have included the Thornton Park Central building (located in the South Eola neighborhood) which then paved the way for The Sanctuary, 101 Eola, and The Paramount in the late 1990’s early 2000’s. These additions cemented South Eola as the ‘it spot’ for trendy shopping and dining in Downtown Orlando. This model continues today with the Camden Thornton Park apartments (also in the South Eola neighborhood), CitiTower, and the Camden Lake Eola apartments.
From 2008-2011 a not-for-profit organization named the South Eola District was formed in order to help promote the neighborhood, which they dubbed “the best little neighborhood in Orlando.” While the organization dissolved with the expansion of Orlando’s Main Street program, the South Eola District name is still referenced in many real estate listings and city websites.