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Winter Park is a great older/historical type community. It's built on "old money" so expect to pay at least $300K on the mid to outer skirts of Winter Park. It's the land prices that's going to hurt you. They have great older houses, beautiful shadowing trees, a great little downtown and a lot of cache associated with it's address. We go to the Art Festival there every year.

There's also a couple of ritzy communities in Orlando like Aislesworth and Lake Nona that are home to a bunch of celebrities that have vacation homes here. Aiselworth is very private and exclusive. They generally have great/exclusive accesses to lakes and rivers for boating.

The city of Lake Mary has kind of the same cache as Winter Park. The communities there are relatively new and it's built on tech money (a lot of tech companies have offices there).

Again, location location location! In the heart of these areas expect to pay premium prices. Despite what people are waiting for the real estate market is still a bull market. But there are enough different communities in these areas or around them that I'm sure you'll be able to find something you'll like. Happy Hunting!
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