Winter Garden FL is the best small town in Florida to retire in. Actually I don't not even think that it is close. I am familiar with The Villages and many other retirement communities and cities. At some point they may be fine. If you still like the small town feel and walking down the streets of the downtown area then Winter Garden is definitely for you.
Many but not all retired residents came here to be close to the parks. Namely Disney and Universal. The southern part of the city is right up against the border of Walt Disney World property and many witness the fireworks every night. We only go when the grandchildren want to but it is nice to have it close by.
My favorite part is the actual city. The downtown area and all of the local trails, lakes and parks. We often go out to eat and there are a lot of choices and newer ones are showing up everywhere. The city is clean and safe and most people are friendly enough to speak to.
The city is attractive enough that any visitors you many have will like it also. Spend some time on this site. Learn more about our city and then reach out to me when you are ready to purchase your new home here in the best small town in Florida to retire in.