#26. Maitland
Long known as a vacation spot because of its tropical climate and proximity to Florida theme parks, Maitland’s high-quality amenities draw many affluent families. The city has several parks along waterways, such as Lake Lily and Lake Sybelia, which attract boating enthusiasts. The real estate scene in Maitland includes a number of century-old homes on tree-lined streets. The prominent Orange County School District receives praise from parents and students.