The Metcalf Building has stood at Orange Avenue and Pine Street since 1923, which means it predates the theme parks, the interstates, and any reason for a Central Floridian to say the words "Reedy Creek." Ten stories of Chicago-style brick, about 38,384 square feet, dedicated in 1924, still collecting rent a century later.
Plenty of people pass that corner every day on the way to a meeting or a coffee run. Far fewer know that Walt Disney's people once ran a secret land acquisition out of an office upstairs.
Bank, drugstore, county office, World Cup headquarters, law school, basement dive bar. The Metcalf Building has held more jobs than most people do in a lifetime, and in August 2026 it started another one.
Table of Contents
A Skyscraper, Back When Orlando Barely Had Any
Construction started in 1923, during Florida's land boom, when Orlando was working overtime to convince itself it was a real city. The client was the Orlando Bank & Trust Company. What went up was one of only three structures on Orange Avenue tall enough to earn the word "skyscraper," which then meant ten stories or more. The competition: the Angebilt Hotel building, which opened the same year, and the bank building at 1 North Orange.
A.G. Bentley built it in the twentieth-century commercial style, and for a time it was considered Orlando's tallest skyscraper, a title that in this city has roughly the shelf life of a gallon of milk. The corner storefront went to the Lucerne Pharmacy, which held it until 1926. By 1936 the same square footage was ringing up prescriptions under the Liggett Drug Store name.
The address turned fashionable almost immediately, which was the point. Ten stories reads as modest now, dwarfed by nearly everything that has gone up along Orange Avenue since. In 1924 it was a statement: the Metcalf Building asking that Orlando be taken seriously.
How the Metcalf Building Got Its Name
Booms end. This one ended hard. Orlando's banking sector was devastated by the Great Depression, and the Orlando Bank & Trust Company failed and closed in 1929, less than six years after cutting the ribbon on its brand new tower.
Enter H.W. "Henry" Metcalf, a real estate investor. In 1930 he bought the building for a reported $125,000. Read that number again: a ten-story downtown high-rise, for less than half of what a median Orlando house costs today.
The name went on, and it never came off. Ownership moved to the Florida Bank at Orlando in 1933, and the tenant roster over the following decades ran through Orange County government offices and a long parade of firms whose signage nobody remembers. Which is the genuinely funny part. Metcalf held the place for three years. His name has outlasted the bank that built it, the pharmacy on the corner, and every owner since.
The Tenant Nobody Was Supposed to Know About
Here is the part that stops conversations. In the 1960s, The Walt Disney Company took space in the Metcalf Building, the top floor by most accounts, while it secretly acquired the tens of thousands of acres of Central Florida land that would become Walt Disney World.
Secrecy was the entire point, and it held. A deal that reordered the regional economy got worked out a few floors above a downtown sidewalk while everyone downstairs went about their Tuesday.
The Reedy Creek Improvement District, the special governing district created to handle roads, utilities and water on Disney property, worked out of the Metcalf Building as well, until permanent offices were finished on site at Walt Disney World. For a stretch there, one downtown Orlando address housed the administrative machinery of a resort that did not yet exist.
Soccer, Law School, and the Civic Years
Disney gets the headline. The résumé is longer.
Orlando's Downtown Development Board was headquartered in the building in 1987. Then came 1994, when Orlando hosted five FIFA World Cup matches and the Orlando/Kissimmee Host Committee ran the operation from inside the Metcalf Building. The tournament brought more than 80,000 visitors to the region and an estimated $82 million in economic impact.
In 2002, Florida Agricultural and Mechanical University temporarily housed its College of Law in the Metcalf Building. Bank, county office, World Cup headquarters, law school. That is a range most buildings never get anywhere near.
What Was Hiding Under the Linoleum
By the 1980s, decades of alterations had buried much of the building's original ornamentation. A $2.5 million renovation in the mid-1980s went digging for it.
Crews removed old concrete panels and found original detailing underneath. They stripped away layer after layer of linoleum on the ground floor and hit an Art Deco terrazzo floor. On the second floor was an elaborate ceiling covered in painted plaster rosettes, sitting there unseen until someone thought to look.
Somebody, at some point, had looked at that ceiling and decided to cover it up. The renovation reversed that instinct, and the Metcalf Building now turns up on the city's historic preservation walking tour of downtown.
Thirty-Seven Years of Tanqueray's
Down in the basement sat Tanqueray's, a dive bar that spent more than three decades as a downtown Orlando institution and was loved for being exactly what it was and nothing more. It even picked up a strange piece of immortality along the way: a nod in "The Sims."
Tanqueray's closed in December 2025 after 37 years beneath the Metcalf Building. If you spent any part of your twenties downtown, you probably have a Tanqueray's story, and it is probably a good one. Its closing emptied the one space in the building that anybody visited on purpose after dark.
Three Owners, Five Years
The last five years have been busier than most decades in this building's history:
- 2021. Massachusetts-based FoxRock Properties buys it for $9.79 million, working out to about $249 per square foot.
- August 2025. It sells again, this time to a New England realty group.
- August 2026. First Capital Property Group takes over and announces plans for office condominiums and executive suites.
The 2021 sale put the property in out-of-state hands at roughly $249 per square foot. Two transactions later, it has an owner with a different idea about what the place should be.
The Office Condo Bet
First Capital Property Group is not running the apartment conversion play, which by now is the reflex move for aging downtown stock. FCPG is working both sides of the deal: full-floor office condominiums for sale, and leases for firms that would rather not buy. The leasing side includes executive suites on the fifth floor with shared restrooms, breakroom, kitchen and lobby, with janitorial, electric, water and internet folded into the deal and keypad entry on each office. Retail space is available at street level too.
Each floor of the Metcalf Building runs about 3,483 square feet, so a single company can take an entire level instead of splitting a floor and sharing a hallway with three other firms. Across ten stories and a basement the building totals roughly 38,384 square feet, which makes it small for a high-rise and unusually flexible because of it. The AC-3A/T/HP zoning permits a range of professional and creative uses, and the dual frontages come with signage exposure that tenants buried in a shared tower never get.
Behind the pitch is more than $1.5 million in capital improvements committed over the past 36 months. That covers full elevator modernization and a new TPO roof system, both listed as fully funded for the second quarter of 2026, plus upgraded HVAC, water source heat pumps and circulation systems. None of that photographs well. All of it decides whether a hundred-year-old building gets another hundred years.
Parking, the eternal downtown complaint, gets addressed head on. A private surface lot next to the Metcalf Building provides at-grade spaces, which is uncommon in the core, and reserved spots are available in the Plaza Garage and the 18 W Central garage a block north. The lobby has been renovated. There is a virtual tour of floors four through seven for anyone who wants a look before booking a walkthrough.
For a local business owner, the full-floor math is the interesting part, and leasing availability covers firms not ready to buy. Owning a floor downtown, rather than renting one, is not an option that comes up often.
Why the Metcalf Building Still Matters
The corner of Orange and Pine gets described as downtown's most iconic pedestrian intersection, with more than 27,000 daily foot and vehicle passersby. That is a marketing line wrapped around a real number, and the number is the case for the building's future. The surrounding blocks back it up: SunRail, City Hall, Lake Eola, the Kia Center and the Dr. Phillips Center for the Performing Arts all sit within a short walk, with I-4 and SR 408 minutes away.
Its past is the case for paying attention right now. The Metcalf Building is one of the three skyscraper-rank buildings the 1920s put on Orange Avenue, and a rare surviving link to Orlando's pre-Disney-boom skyline. It has stayed upright through Jazz Age optimism, a bank failure, the Depression, a secret land deal that reordered the regional economy, a World Cup, a law school, and a dive bar's entire 37-year run.
There is a quieter case too. The Metcalf Building was never built for anybody's vacation. It was built for a bank, bought by an investor, and filled over the years with county staff, law students, committee organizers and people getting a drink after work. Downtown history in this city tends to get told through what was demolished. This one is still here, still working.
Every city keeps a few buildings that function as memory, and Orlando keeps very few. The next chapter belongs to First Capital Property Group, which says it wants the historic character preserved while it sells the floors off one at a time. Preservation and a sales pitch do not always point the same direction. Which one wins here is worth watching.
🔥 If you're fascinated by Orlando history like I am, well, there's plenty more where this came from, right here.
Sources:
https://www.thehistorycenter.org/skyscraper-survivors/
https://www.theorlandoguy.com/episodes/orlando-history/historic-downtown-orlando-tour/
https://www.clickorlando.com/news/local/2026/08/20/historic-metcalf-building-in-downtown-orlando-gets-new-owners-plans-for-office-redevelopment/
https://totalcommercial.com/listings/60255
https://www.orlando.gov/files/sharedassets/public/v/1/departments/edv/city-planning/historic-preservation/walkingtour_brochureweb.pdf
https://www.orlandoweekly.com/music/historic-downtown-orlando-property-the-metcalf-home-to-tanquerays-bar-sold-to-new-england-realty-group-30215532/
https://www.costar.com/article/630149869/foxrock-properties-acquires-metcalf-building-in-downtown-orlando
https://fcpg.com/the-metcalf/
https://www.loopnet.com/Listing/100-S-Orange-Ave-Orlando-FL/18147392/
https://fcpg.com/the-historic-metcalf-building-lease/
