My last 2 houses did, both in climates where they could be used about 4 months out of the year. I/we used professionals to open and close it but otherwise maintained it ourselves.
Use of the pool dwindled over the years. When we moved to the second house, DS went off to college and used it only infrequently in the summer. As DH developed some chronic health problems, his skin couldn't tolerate pool water (gave him itching attacks) and he was uncomfortable out in hot sun. I tended to do a full cardio workout in the gym every day or take long bike rides and jumped in the pool only after getting hot and sweaty after pulling weeds. Well, it was really nice for that!
We downsized in mid-2015 and would definitely not have bought a house with a pool. With both houses, buyers tended to be one extreme or the other: a swimming pool was a huge plus or it was a deal-breaker. There were more of the latter.
In addition to routine maintenance, there's a lot of expensive stuff that can go wrong. In the first house I had to replace the pump and the filter and at one point paid to have them tear up the concrete around the pool to replace leaky piping. The second pool was gunite instead of a vinyl liner, which was easier to maintain (no leaks) but at one point we had to drain the pool, have the gunite patched and repainted, and fill it again. I'm glad not to have that responsibility now!