On average, listings lease in the $10's per square foot per year. The Winchester region is experiencing a decline in rates. In the last 3 months, the median rate fell $1 per sqft per year. That's a 5% decline in rent.
In the last 90 days, 12 listings have been made available, which means leases are probably going fast. You'll want to be prepared to make an offer immediately. About 183% of the available space in the Winchester 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.
Even though the median size is 2,690 sqft, there are still 0 office spaces below 2,000 sqft. Most properties in this region are approximately 2 stories. Most buildings in this market were built in 1989 and are Class A.