Downtown Orlando has some of the most varied architecture in the area, featuring buildings from the 1920s and 1930s standing alongside modern skyscrapers. Nowhere is this more apparent than the Old Orlando Railroad Depot (100-102 W. Church St.), also known as Church Street Station, a three-story Victorian-style building opened in 1889. In 2008, it received a 32-story addition next door that offers 377 luxury loft-style condos.
Also downtown, the Orange County Regional History Center (65 E. Central Blvd.), formerly the old county courthouse, is a great example of French Beaux Arts architecture. It was built in 1927 for a cost of $1 million.
Winter Park has a variety of Victorian-style mansion homes, built in the late 1800s, when rich families from the north built their winter homes here. Rollins College, also in Winter Park, was founded in 1885, and has many Spanish-style buildings. The best way to see both styles is via the Winter Park Boat Tours.
Just north of Orlando,  Eatonville, established in 1887, is known as one of the first incorporated black towns formed after the signing of the Emancipation Proclamation. Many buildings from that era remain.
On the south side, downtown Kissimmee is a registered historical district, with most buildings from the late 1800's. A highlight is the Osceola County Courthouse, not only one of the state's oldest, but the only one still in daily use since it opened in 1890.
The city of Celebration, a Disney-designed community, actually didn't exist until 1994, but as with anything Disney, accuracy was important when recreating the New Urbanism feel of 1930s America. Celebration's Town Center design is a mixture of Art Deco and Caribbean/Cuban flair.