Jackie Gleason’s Round House - 1960 - Peekskill, N.Y (USA)

According to a 1960 issue of Popular Mechanics, "the many talents and accomplishments of Jackie Gleason put him out of the ordinary class of home builders," which, perhaps, explains why the iconic comedian, actor, and musician opted instead for this remarkably kooky Round House atop a forested hill in Peekskill, N.Y. Never one to chose functionality over novelty or fun-factor—just take a look at his "arrestingly pastel" party pad in Miami—the secluded getaway looks like a shrine to all things round, with everything from the shape of the home to the groovy, modular furniture inside boasting utterly corner-free design, all done with a level of success that's never since been achieved.



To ensure that every side of the donut-shaped main floor—which doubled as his broadcasting studio—enjoyed crackling hearth exposure, a 40-foot-tall, three-headed marble fireplace sits suspended from the center of the room. Also available on the nine-acre property? A storage space that looks, to use a bit of architectural jargon, exactly like a UFO. Tour Chez Gleason in full, right this way.