The pools were added in the 1980s by the current seller.
A look inside the Spaceship, which is built around a hanging fireplace. Although Gleason originally intended to use the space for storage, it can be adapted to house guests.
Nicknamed "The Spaceship," the small UFO-inspired cottage includes a tiny utility kitchen, bathroom, and storage.
The built-in office and broadcasting studio allowed Gleason to comfortably work from home.
A look inside one of the bedrooms with a round bed and a television embedded into the ceiling.
The approximately 3,950-square-foot, three-story Mothership includes two bedrooms and two full baths.
Right angles were eschewed in favor of curved, organic forms. "If you look at the ceilings, the woodwork looks like rowboats," continue the agents. "They are the trusses that hold the house up—there are no cross support beams, because they would have had right angles."
The pillars are built of Douglas fir, while the sturdy footings are made from aircraft aluminum.
The cap for the fireplace was so massive it had to brought in by helicopter.
A look inside the den with a second fireplace. "Jackie actually had to buy the quarry in Italy as they were running out of marble for the home," notes the listing agents. "Jackie brought the workers over from Italy to build and place the three connected fireplaces. The quarry passed with his estate when he passed away."
The home features three lavish fireplaces—each built of Carrara marble—weighing a total of 240 tons.
Next to the bar, a billiards room branches off of the circular Great Room and leads to a cozy den.
The property includes four bars—one of which seats 13 people.
All the flooring curves with the wood, and has been bent to a circle fashion using a steaming machine. The house includes tens of thousands of pieces of wood, all curved by hand.
Full-height glazing wraps around the home for spectacular views of the woods.
"The concept of the home is a musical note—hence the roundness of the design. As with a note, it never ends," explain the RE/MAX TOWN & COUNTRY listing agents.
Here's the entrance to The Mothership, which is flanked by lush landscaping.
Used as a retreat from New York City, the Hudson Valley home includes a broadcasting studio so Gleason could work in a quieter environment.
Topped with a copper roof, the round house is the largest of the property’s three homes. Gleason affectionately nicknamed it “The Mothership.”