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Depending on your budget, wants, and needs, a pool enclosure can be a worthwhile investment. It all comes down to how much you use your pool, and what it would mean to you to have year-round access to it.

If you know that you'll swim in your pool a lot, then having an enclosure means you don't have to worry about the weather. It's also a lot easier to maintain the water, because you don't have to deal with leaves falling into the pool, and the water's chemical levels tend to be more stable.

A retaining wall can only function as a fence if it’s high enough on all sides to prevent someone from accidentally falling into the pool. However, most retaining walls retain dirt, which means their purpose is not related to safety. There would need to be nothing on the other side of the wall for it to be considered a fence, but in that case, it wouldn’t retain anything and would cease to be a retaining wall.  

If you live in an area where pool enclosures are expected, like in Florida, having one won't necessarily increase your home value. However, it's worth noting that in warm climates, a pool can add $11,600 to $95,000 to a home's value. 

On the other hand, if you're in an area where pool enclosures are not common, having one might set your home apart from the crowd. Depending on the appraiser, you may see an additional $25,000 to $27,000 or more for an enclosed, inground pool when it comes time to sell.

Building an inground pool is a job best left to the pros. Excavating the area and building the pool requires heavy equipment and specialized training, and pools have complex plumbing and electrical systems. Unless you’re experienced in these areas, you’re better off hiring a pool contractor to make sure the job gets done safely and correctly.