We recently bought a house with a pool. We are not in the Midwest but do have 4 seasons. We swam until October and will probably be able to swim again April/May. We were not looking for a pool but I love having it. It is salt water, newer and completely automated so there is very little work. The age and type of pool and equipment will determine the work/expense needed. We did have a separate pool inspection before we bought the house.

We keep the pool open year round as winters are typically mild. We did heat it last weekend for DS’s Bday so he and his friends could swim. I don’t anticipate doing that often though. There is also a hot tub portion that we can heat and use separately.

We do not have much yard space however there is a large park in our neighborhood. It is also not a substitute for joining a pool for us. Our neighborhood pool is a 2 minute walk away and the kids love going there too and will do swim team there.

We also had a large lot before (4 acres) but were not in a neighborhood. My kids love being in a neighborhood and being able to ride bikes to friends houses or the park. They do not miss the yard at all and love having a pool. A lot of the playing seems to be in the culdesacs or at the park.

So I would say whether or not you would miss the yard would depend on what the setting is like and if there is a park close by.