Sprawling acreage. Top-notch arena footing. A barn that could decpostcard. And, you know, a mansion to go with all of it…

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These are just some of the real estate challenges facing America’s billionaire horse show dads (and moms) these days, and top on the list is none other than Bill Gates. While rider-daughter Jennifer pursues her degree at Stanford, Bill’s been busy buying up a host of equestrian properties around the country, including diet guru Jenny Craig’s ranch in Rancho Santa Fe, California, and two posh lots for a cool $5 million in Wellington, Florida’s Mallet Hill Court—a neighborhood where he already owns six properties.

What’s it like to shop for horse farms when your Bill Gates? If it’s anything like Realtor.com imagines it, probably hella fun. From Hawaiian hideaways to Olympic-level compounds and all the bucolic acres in between, here are eight, breathtaking equestrian properties for billionaires.