What ever you do, don't be foolish as to how you sell and then buy another property.
Read here as to how to sell: http://www.trulia.com/blog/steve_31/2012/08/mortgage_broker_
Read here as to how to get your best overall deal:
Lake Nona is new and exciting and being built up quickly, while Windermere is well-know, established and considered very prestigious. Both have advantages. The most important factor is which will make you feel most comfortable and feel more like "home" to you. Both would be considered good solid investments.
Feel free to search for properties in both areas from my website: http://www.OrlandoRealEstateLady.com. If you have questions, you can contact me at 407-463-6869 or at LeslyeH@att.net, or through my website. I will be happy to show you around both areas so that you can get a better feel for them.
Leslye Henderson, Realtor
Weichert Realtors Hallmark Properties
8958 Conroy-Windermere Road
Orlando, FL 32835