The typical asking rate per listing is in the $20's per square foot per year. The Winter Park submarket is going through a a boost in rates. In the last 3 months, the median rate rose $24 per sqft per year.
In the last 90 days, 24 listings have come on the market, which means new listings are probably leasing quickly. You'll want to be prepared to make an offer immediately. About 121% of the listings in the Winter Park are subleases, so you might be able to sign a shorter term by taking over a previous 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 1,330 sqft. Most properties in this area are approximately 2 stories. Most buildings in this market were built in 1981 and are Class B.