I just sold a unit in Winterpark for $80,000 and am in the process of buying one for $92,000 for a customer. I have sold and bought a number of units in Winterpark. Most of the units are now in the low 100's which means they have come back a long way in the last two years.
Winterpark has great units with 1,246 sq. ft. and their proximity to beaches and Naples is incredible.
So for you - it depends on what you want to do. If you want to just sell your place in Winterpark and you have no other intentions - then you could wait until after the season and see what's happening. If you are interested in selling your place in Winterpark and buying another condo in Naples - now is the time. Prices are rising and inventory is shrinking - buying now is a very good thing to do but if you are only interested in selling then wait prices will escalate.
Please let me know if I can help,