The Orlando suburb of Winter Park, Florida, works hard to maintain the luxury resort town feel it was founded with nearly 140 years ago, even as it has grown into a city. Walk through Central Park or visit the shops on Park Avenue and it's easy to imagine what made this an attractive playground for snow-weary Northerners.
Penthouse 404 in the old Alabama Hotel is a piece of that history, modernized and retrofitted for the aristocratic person of leisure today, and now offered at a price tag of $2.49 million.
Padgett McCormick of Kelly Price & Co. has the listing.

Sitting on the southeastern bank of Lake Maitland, site of some of Winter Park’s most expensive home sales, The Alabama started life as an orange grove in the 19th century. It changed hands through a series of the city’s founding families before being developed into a hotel in 1921, originally to attract vacationers and give them a sales pitch for the platted neighborhood around it.
Margaret Mitchell, author of "Gone With the Wind," and triple Pulitzer Prize-winning playwright Thornton Wilder were among the hotel’s more notable guests.
In the 1980s, the five-story building was converted into condos. The 80 hotel rooms were combined into 19 units.
The journey to the three-bedroom, three-and-a-half-bath Penthouse 404 begins at the iron gate and the brick driveway lined with palms and Florida landscaping. “The entrance sequence is really beautiful,” McCormick said.

The two-story condo begins on the fourth floor, starting with a foyer featuring intricate millwork paneling. That’s the work of Winter Park-based custom home builder Z Properties, which gave the condo an overhaul in 2019.
In order to make the 2,709-square-foot space feel like a full luxury residence, Z hid many of the access doors inside the condo. The foyer contains hidden doors for both the primary bedroom and the downstairs guest bedroom.

“The way you walk into the foyer, and you don’t have multiple doors, it’s not compromising on the luxury of the design in what is not really an oversized space,” McCormick said.

The wood cabinetry in the kitchen is also hiding the door to the den, as well as the stairs to the second floor. The den includes full-sized windows and access to the suite’s terrace, a turf-covered and landscaped balcony overlooking the lake.
Penthouse 404 is the only unit in the building to include a terrace.

The building itself includes a dock on the lake, as well as a pool and patio for residents.
The city had just over 1,000 residents when The Alabama was built. Today, it has nearly 30,000, but even that reflects only a 5,000-person increase since the year 2000, according to the Census Bureau.
Even with all the modern touches, the setting still carries the feel of an era when time moved a little slower.