Below is a list of 9 structures once considered iconic in Orlando that have been demolished or lost to redevelopment.
(Note: Some entries—like sports venues or transportation hubs—might be thought of more broadly as “structures” rather than conventional office or hotel buildings, but each played a significant role in Orlando’s history.)
1) Woolworth-McCrory Building
Once a downtown retail landmark at 101 South Orange Avenue, this Art Moderne–style building (with elements dating back to 1888) was demolished in 2003, marking the end of an era for downtown five‐and‐dime architecture. People still talk about their hamburgers and cherry Cokes.
2) American Federal Building (Round Building)
A striking example of mid‑century modern design located at 455 South Orange Avenue, it was expanded in 1973 and later demolished in 2015 to make way for new cultural developments (now partly remembered through salvaged architectural elements, one of which is on display in Heritage Square in downtown Orlando).
3) Orange Court Hotel
Constructed in 1924 in the Spanish Revival style and once famed for its vine‑covered balconies, tropical garden, and early steam‑heated pool, this hotel closed in 1960 (with a brief revival) before being demolished in 1990.
4) San Juan Hotel
An 1885 hotel (later expanded with an eight‑story wing in 1922) on the corner of Orange and Central Avenues, it changed hands several times and—after periods of financial struggle and even a brief reopening—was demolished in 1980 despite preservation efforts.
5) Parliament House Resort
The former Parliament House resort—a beloved LGBTQ+ landmark on Orange Blossom Trail that operated for 45 years—closed its doors on November 2, 2020 and was slated for demolition soon after. Demolition began on January 4, 2021, clearing the property for redevelopment while efforts were made to preserve the resort’s iconic sign as a tribute to its storied queer history.
6) Ronnie’s Restaurant
Ronnie’s Restaurant was a beloved Jewish delicatessen and bake shop in Orlando, established in 1956 by Larry Leckart and his wife, and quickly became a local institution known for its hearty deli fare and strict dining policies. After nearly 40 years of serving over 21 million customers, the restaurant closed unexpectedly in 1995 when its lease was bought out by developers, and its building was later demolished to make way for new mall redevelopment, leaving behind a lasting legacy in Orlando’s culinary history. Two of the restaurant’s neon signs were rescued by the Orange County Regional History Center and the Morse Museum.
7) Tinker Field Grandstands
While the open‑air ballpark’s site is now commemorated by Tinker Field History Plaza, the original wooden grandstands and ancillary buildings—once the spring training home for several Major League teams—were torn down in 2015 to accommodate adjacent stadium renovations.
8) Eddie Graham Sports Complex/ Orlando Sports Stadium
The Eddie Graham Sports Complex, originally opened as the Orlando Sports Stadium in 1967, was a modest indoor arena that hosted a wide range of events—from rock concerts by bands like Led Zeppelin to professional wrestling and boxing matches. Renamed in honor of wrestler and promoter Eddie Graham, the venue eventually suffered from severe code violations, including inadequate air conditioning and deteriorating facilities, which led the Orange County Building Department to close it down. The arena was demolished in November 1995, and the land where it once stood has since been redeveloped into a housing community.
9) Original Orlando Public Library
The original Albertson Public Library, which opened in 1923 and served as Orlando’s first public library, was demolished in 1964 to clear the way for a modern, expanded facility. Captain Charles L. Albertson’s generous donation of 12,000 books helped establish the library, but as the city’s population and its collection grew dramatically in the mid‑20th century, the Neoclassical building became insufficient for the community’s needs. Its demolition marked the end of an era, paving the way for the new Orlando Public Library—dedicated in 1966—which now commemorates the legacy of its predecessor.
The old VFW building down on Lake Ivanhoe, plus the OUC Power building across from the Lake Ivanhoe