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Every house (except those while in Oxford) that I've lived in has had a pool. It was always my job to take care of the pool growing up so I know a thing or two and second what ridgereb said. I would say it is better to buy a house with a pool, then install one yourself as you rarely see the full ROI (unless your the only pooless house in the neighborhood, then it might be a good idea to look into building one). If the pool is more than 10 years old, you'll probably have to replace the liner (if so equipped) or if its gunite/shot crete look at redoing the plaster(10-15k), so take that into consideration when making an offer/looking at the pools. Check out the filter pump/filter. The older, single speed pumps are very inefficent. Now-a-days, the pumps are very energy efficient and I would consider a variable speed or two speed pump if the pump needs replacing. You can control the amount of flow depending on what is needed and save significant costs on your energy bill. During the summers down here, you will need to run your pool 8-12 hours a day to filter your water twice and keep the pool clean/circulate the chemicals and with running the A/C and pool pump, your energy costs will increase. If you have a straight chlorine pool, you will use a lot of it during the summer as chlorine becomes less efficient the hotter it is, so a chlorine/salt generator is a wise investment.

As for insurance costs, your monthly premium might go up, but not significantly. Sometimes, they'll give you a little bit of a break b/c you now have 10, 20, 30k gallons of water at the fire departments disposal if you ever have a fire. It would be wise to get a liability umbrella policy, as a pool is an 'attractive' nuisance and if an accident would occur, you are covered. Most umbrella policies are inexpensive and are well worth the additonal piece of mind.