We are not retired, but we have three properties which are completely paid for.
Property one, principle residences, we live here as we both work in the area. Once we hit our liquid savings goal, it will be sold and we will split time between property two and three.
Property two. a cottage/cabin in a summer area. It is a one minute walk from the water and will serve as our late spring to mid autumn home. It is old, needs work, but will do the job. Purchased about 15 years ago, paid off in 5 years
Property three, a place in the mountains of BC for skiing. It is very small but works for us as it is just the two of us. Purchase d about 10 years ago, paid off in 5 years
The key for us was, we did not but the best property. Our cottage is not waterfront, but has access, so it cost about 1/8the price. Our ski place is very small, (less than 300 sq feet) but has everything and is in the best location.
So I think it is about "settling" i suppose, and focusing on the long term.