Highlights of Orlando’s historical landmarks

Theresa Hus
5 min readApr 6, 2023

When people talk about Orlando, the first thing to come up in the conversation is going to be the theme parks. Many people know about Orlando’s attractions worldwide, and it’s no surprise. Undoubtedly, there’s a theme park paradise and world-famous nightlife here, Orlando becoming a symbol of the US way of having fun. As one of the most visited cities in the world, and a real tourist magnet with uncountable attractions to visit, Orlando, Florida, is the largest metropolitan area after Miami and Tampa. It has the 13th busiest airport in the US and the 29th worldwide. Orlando is most known for the Walt Disney World Resort opened in 1971, and the Universal Orlando Resort, which opened in 1991 as the extension of Universal Studios Florida.

There are tricks for visiting Disney on a budget on the internet, but even if you have a budget for it, there’s only so much cotton candy and fun one can have. Especially as an adult. When you have already had a blast with your kids, there are still many places to check out in Orlando for a different experience. The city has 51 listed historical buildings and other sites to see and discover bits of history and prominent personalities the city has been home to. Realtors in Orlando FL can help you discover historic buildings and newer ones that could become your home if you are planning to become a resident of this city.

There’s plenty of good material for visiting, either after crowded theme parks or as an activity standing as a “main course” on its own. Here are a few highlights of the most interesting historical landmarks to visit during your stay in Orlando!

Old Orlando Railroad Depot

The railroad was built in Orlando in 1880. A year later, in 1881, a station was constructed, followed by a second one in 1886. The second brick building by Henry Plant was an important event in the history of Orlando becoming a city. H.H. Richardson served as an inspiration for the style of the building. The landmark can be found on 76–78 W. Church Street and has been listed among Orlando’s Local Historic Landmarks (OHL) and in the National Register of Historic Places (NRHP) since 1976.

Well’sbuilt Hotel

The building that Dr. Wells constructed in 1926 served as a hotel for African Americans during segregation when there were no other options for lodging in Orlando. Ella Fitzgerald and Jackie Robinson are famous guests of the hotel. Still, many black athletes and entertainers stayed here and performed in the nearby South Street Casino for the black community. The hotel’s address is 511 West Street, and the building has been part of the OHL and NHRP since 2000.

Dr. Phillips House

Col. Peleg Peckham built the house for his daughter in 1893 as a wedding gift. Very soon, in 1912, the house was sold to Dr. Phillips and his spouse, Della, who decided to remodel the building after the plans of L. Percival Hutton, architect. Hutton added the Greek Revival portico, new bedrooms, and the cellar. He modernized the building by changing the gas lights to electricity. The structure is unique in Orlando because it’s the only mansion in the city carrying the specifics of 19th-century Shingle-style architecture. The citrus magnate Phillips family was one of the first millionaires in Orlando. They invested their money and prestige in supporting the arts and organized many cultural events hosted at the mansion. Currently the house is a bed and breakfast, and it has been listed on the local and national registers of historic places since 1979. 135 Lucerne Circle is the address of this iconic landmark.

Orlando Utilities Commission Administration Building

Designed by architect Richard Boone Rodgers and serving today as the Aloft Hotel, the building is a beautiful example of Modern Movement. The building was originally opened in 1967 as the OUC administration office building. The exterior is covered with granite panels and precast concrete panels. The windows have aluminum frames, and the windows on the first floor are large plate glass units. The building is OHL, NRHP since 2012. Address: 500 S. Orange St.

Jack Kerouac’s House

1418 Clouser Avenue is one of the most iconic landmarks for literature fans since Jack Kerouac, the famous American writer, lived in the house. While living in this house, he wrote his most successful books, On the Road, and the follow-up, The Dharma Bums. Kerouac wrote his novel, The Dharma Bums, in only 12 days while living in this home. He mainly wrote at night and in the shadow of the oak tree in the backyard of the building. The building of historical importance for literature enthusiasts is managed today by the Jack Kerouac Writer in Residence Project of Orlando, a nonprofit group offering opportunities for writers and poets to live and create in the home for a period. The simple Frame Vernacular building built in 1920 has been renovated to have the looks and vibes authentic to Kerouac living there. The house became the newest site to be added to the National Register of Historic Places in Orlando.


This Queen Anne-style building at 37–39 Magnolia Avenue was constructed in 1886 by Englishman Gordon Rogers. It hosted the English Club on the second story of the building. This unique building has metal sliding, which was unheard of in Florida then, and had to be shipped from England. The English Club hosted a variety of live performances and dances. The building is listed on the NRHP as well as on the OHL.

The Hunt-Branson Building

Located on 23–25 W. Church Street, the Hunt-Branson Building is a well-preserved commercial structure dating back to the early 20th century. It is among the early buildings on Church Street, Orlando, built in the year 1911.

J. J. Bridges House

The Bridges House was the first of its kind in Orlando. It was built in the Colonial Revival style in 1916. Its importance lies in the fact that it inspired a new generation of buildings with a more elegant and simplified style than the “great houses” characteristic of Edward Pringle Hyer in the late 1920s and 30s. The house was where Rev. John J. Bridges and his wife, Isobel spent their retirement years. The residence can be found on 704 S. Kuhl Avenue and is listed on the OHL and NRHP.

Greenwood Cemetery Orlando

Established in 1880, the Greenwood Cemetery is a municipal cemetery in Orlando and an unusual city attraction. Not exactly a landmark, but an essential spot in the city’s history, Greenwood Cemetery is a scenic place to take a quiet walk. There is a possibility to visit the moonlight-lit graveyard and ponder upon existence while visiting the 100 graves of notable Orlando residents.

To wrap up,

With its many sites, Orlando has been attracting visitors to its famous theme parks since they were opened. There are many must-see attractions in Orlando, Florida, and while theme parks might be the most popular, there are a few other things worth checking out. Local historic landmarks serve as testimonials to the life of great people whose names are closely tied to the city of Orlando. Historical landmarks provide a glimpse into the past and offer the opportunity to take a look at the original architecture that adds value to the cityscape of Orlando. Among all the Disney stuff, a historical tour can be a one-of-a-kind alternative experience on a visit to Orlando, Florida.



Theresa Hus

Theresa has single-handedly created the entire Sales and Marketing Training Program at RealEstateAgent.com from scratch, and has closed approx 20m in sales.