Most listings are in the $20's per square foot per year. The Winter Park region is going through a a rise in rates. In the last 3 months, the median rate increased $1 per sqft per year. That's a 4% rise in rent.
In the last 90 days, 26 listings have been made available, which means new listings might be going fast. You'll want to be prepared to tour spaces as quick as possible. About 4% of the available leases 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 market are close to 2 stories. Most buildings in this region were built in 1981 and are Class B.