Usually, people start thinking of retirement and retirement destinations three to five years before they will be ready to retire. When you start "thinking" that's the very best time to make contact with your "New Best Friend". This would be an experienced, full-time real estate agent in the location you are considering.
When you make your initial contact you can tell the Agent that you are just starting your search for information and tell them what your wish list includes. Very important to include in this information is the price range you feel you would be most comfortable with. This, of course, can change as can any of the other criteria you provide. Make your first list include everything you would really like. If a pool is something you think you want, include it. Single story home vs two story, age qualified community, etc.
A really good Agent, and one you will be comfortable working with ,will send you listings at the frequency you would like. It could be once a week, once a month, etc. This will keep you informed of what is going on in the market. You might find a particular community that interests you. You can then tell your Agent to be sure to keep you up to date on this place or any similar properties. This is also a good time to let your Agent know how you would prefer your contacts to continue - only e-mail or perhaps a phone call once in awhile.
When you make a visit to the place you have been considering as your retirement destination, you will feel very comfortable meeting with your Agent and going to look at the areas & communities that interest you.
Another plus is that all of this is at no cost to you. It's fun to look for properties online but what is really great information is what your Agent will interpret for you regarding the surrounding area, homeowners association information and distances to the airport, shopping and other areas of interest.