The WSJ looks at the cost of pool ownership and concludes that
"It's definitely not an investment," argues Jim Holtzman, financial planner at Legend Financial Advisors in Pittsburgh. "It's a big liability, if anything."
From a financial perspective, over the long term, they are absolutely correct. Yearly pool maintence, increased insurance costs, and opportunity costs all make a swimming pool a liability. But in the Hamptons, all these costs can be recouped by the much higher rental prices owners can command. Maybe the answer in the Hamptons from a financial perspective is don't put one in unless you are going to rent for at least a month each summer.
The most important pool-related real estate investment one can make here is buying a place with room for a pool. You can always put one in later. The risk is that zoning will change and the room for a pool will be eliminated. So get a building permit if possible. And beware of sales listings claiming there is room for a pool; many are inaccurate.

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