K.W.
Hi J.!
We moved to the Orlando area two years ago -- orginally we are from New York. We leased a home in Oviedo (a suburb of Orlando); and now we are leasing a home in Winter Park. The Winter Park/Maitland area is an extremely family-friendly area to live in.
We are right next to the town line between Winter Park/Maitland. The schools are quite good. I've been a public school teacher in other states; you have to be aware of the school districts -- just because it is a nice-looking neighborhood, doesn't mean you child will be assigned to a quality public school district.
I would strongly recommend leasing a home with the housing market the way it is, but it all depends on what your personal circumstances are.
I did find an amazing realtor (by the way, we've learned that everyone knows someone or is a realtor in Florida). Her name is Brenda Cole and she is by far -- one of the most honest, ethical realtors I've found - and we've gone through three realtors. She knows we won't buy a home for one (maybe even two more years) & she's still so helpful finding new neighborhoods for me to look at. Also, she is not the "quick sale" type at all. In case, you would like to rent (lease) a nice home or buy, she could do it all.
Also, I'm in an International MOMs Club that covers Winter Park & Maitland. About 40 moms are members, and it is a great way to get to know lots of different moms & information about the local area and such.
Good luck on your move!
Any info. you'd like to know, I'll help you.