I live in the area and love it here. It's a large city with various areas for shopping, dining, entertaining and active lifestyles. Downtown Winter Garden is renovated with a Saturday Farmers Market; live theatre; many unique, eclectic shops; dining and more. Many events occur in downtown Winter Garden, like parades; Halloween; concerts; art/craft fairs; car shows, etc. http://www.cwgdn.com/.
We also have a large upscale outdoor mall - Winter Garden Village / The Grove - http://www.wintergardenvillage.com/. This plaza offers about 100 shops and some large stores as well.
You can check crime rates through Winter Garden's Police Dept's site -
Hope this helps.
Realtor & Investment Home Specialist
La Rosa Realty, LLC / Celebration, FL
01.407.274.8476 / email@example.com