Winter Park was platted in 1881 around a chain of lakes and a central park, and it has protected that identity ever since -- brick streets, oak canopies, and Park Avenue's boutiques and restaurants a short walk from home. Limited land and historic zoning keep inventory tight, so homes here tend to hold value differently than the rest of the Orlando metro.
Zoned for Orange County Public Schools, with a concentration of well-regarded public and private options that draw families from across the metro.
Winter Park has no CDDs -- it predates them entirely. Any added cost here comes from an HOA where one applies, not a district assessment.