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Florida starts with its two planned towns, one in the south and one by the Orlando lakes. South Florida has Coral Gables, the Mediterranean Revival city George Merrick drew from groves and coral rock. Orlando has Winter Park, the 1881 resort town of brick streets, a chain of lakes and a college on Lake Virginia. Tampa Bay and Jacksonville follow.
One Florida cost runs through every report in the state: insurance. Florida levies no state personal income tax, and the combined sales tax in Coral Gables is 7 percent in 2026. Homeowner and wind insurance runs among the highest in the country, though, and at luxury prices that single line item can outweigh the income tax saving. Price the policy with the house, every time.
Metros
South Florida
Miami-Dade and Broward: planned cities, island neighborhoods, and the mainland streets behind the beach.
Orlando
Lake districts and brick street neighborhoods north of downtown, starting with Winter Park.
Tampa Bay
Historic streetcar suburbs and bayside districts in Tampa and St. Petersburg.
Jacksonville
Riverfront historic districts and beach towns along the First Coast.
Latest Florida Reports
Winter Park, Orlando
Brick streets, a chain of lakes and old Florida polish: Park Avenue runs its boutiques, cafes and museums along a Central Park that has stayed an open public lawn since 1906, Rollins College sits on Lake Virginia at the south end of town, and the boat tour has threaded the canals between the lakes since 1938, about six miles northeast of downtown Orlando.
Median $660,000Walk Score 86
Photo: Ebyabe, CC BY-SA 3.0, Wikimedia Commons
Coral Gables, South Florida
The planned city that kept its plan: George Merrick built a Mediterranean Revival city under a banyan canopy in the 1920s, with plazas, grand entrances, a quarry turned swimming pool and a downtown where every shop sat within a two block walk, about seven miles southwest of downtown Miami.
Median $1,400,000Walk Score 99
Photo: Ebyabe, CC BY-SA 3.0, Wikimedia Commons