Are you looking to downsize from you current home? Winchester is a great town. There are not many drawbacks to living in Winchester either. The tax rate may be a concern to someone who doesn't live in the town now. (It's probably one of the highest tax rates in the area). First time home buyers don't usually look in Winchester for that reason. You should first decide where you want to move to, how much your current house would sell for and what your time frame is. If you have any additional questions for me, please contact me at my personal website. Hope to hear from you soon! - Wed Feb 13 2008, 07:50