I will soon be celebrating my 1st year anniversary as a Villager. Your question is a good one, because you will be starting a new life style, if you are retiring.
I was totally engaged with a full time career and I had the exact same concern when we first gave my retirement serious thought. The fact we did not wish to become bored and house bound was a major factor for us choosing The Villages. I can honestly tell you boredom is never an issue. You will have to put some work into planning out what you wish to do here at The Villages and then get out there and do it. We plan our month with our scheduled meetings, social events, and golfing. Having a weekly recreational newsletter helps a lot. After only just one year, we have very little time where nothing is going on. We also have to include our friends and neighbors in our social time because our Village must be one of the friendliest in The Villages. (Driveway Parties) Then you have to include old friends and family, who all want to come spend time with you at The Villages.
I can assure you, if you get out there and engage the active lifestyle The Villages offers, boredom will NOT be an issue, there are some fun part-time jobs available if you must work. (golf starter/ambassador, community watch, recreational aide, etc. So come on down and enjoy the life and remember life is a gift and it's all about what you make of it!
