Holly Trees next to a pool or house

Don't holly trees drop little berrys?

I have 3 in my yard and they drop all over the place. You gonna be fishing them out of the pool a lot

Planted 10-gallon Eagleston hollies in 2017, but not near a pool. One has grown to be enormous (because of rain runoff from the roof). Looking to top it off with a severe cutback - if it dies, then I'll cut it down and plant something different. I would not plant near a pool.

ETA: consider a row boxwoods, we planted a row of wintergreen boxwoods as a hedge, and they're about 3-1/2 ft tall and healthy. Roots are not a big deal.

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Yes they do drop berries but if you keep them trimmed past the waterline you’ll be fine.

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Not with wind blowing them, and ROUND berries bouncing off lower branches, and bouncing and rolling on ground. Berries will be a mess.

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I was also worried about roots in the long run but we just recently sold the house.

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Holly tree roots are a pain in the arse. We had one planted to screen an ugly shed on neighbor's property. Once that shed was gone, I wound up getting rid of the tree. The roots were so aggressive and thick that they wound up choking out azalea bushes and all the other plants planted around the perimeter of the tree. I could easily see the roots on a holly tres becoming a problem with that wall.

The large one is around 20 ft tall, but I want max 15 ft tall. The breadth of the tree branches is expansive, guessing that the root system is approx 10 ft in either direction.

Almost any tree next to a pool can be a problem.
Source: has palm trees next to pool.
One of the goals of pool management is keeping shite out of the pool. Trees are the enemy.

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A 25 foot tree...3 feet from the pool?

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Exactly.