Most listings are in the $20's per square foot per year. The Winter Park region is going through a decrease in rates. In the last 3 months, the median rate fell $1 per sqft per year. That's a 5% decrease in rent.
In the last 90 days, 38 listings have been posted online, which means new listings are probably going fast. You'll want to be prepared to make an offer immediately. About 3% of the available space in the Winter Park are subleases, so you will probably have to consider a longer term lease. There aren't many listings below 2,000 square feet posted, so finding a space for a small business might be tough.
The standard measurement for office space in this area is around 2,200 sqft. Most properties in this area are approximately 2 floors. Most buildings in this region were built in 1981 and are Class B.