Price: $6,890,000

There’s really only one place to go if horse trails are on your real estate wish list: Barrington Hills. Here, estates of five or more acres, old or new, cater to the equestrian. This is some of the most expensive real estate in the Chicago area, mainly because the houses and lots are so big. One of the most over-the-top pairings of land and shelter listed for sale two weeks ago, asking $6.89 million—only the fifth most expensive property on the market in Barrington Hills.

The architect on the project was the late Len Bauer. He executed a monumental home of 20,000 square feet in a way that conjured ‘alpine retreat’, with the surrounding pine plantation chipping in. “It has Colorado Rockies written all over it,” says RE/MAX agent Marsha Ulbrich, who has represented all three owners of the 1999 estate. Funny enough, the first owner left for Aspen a few years after the home’s completion.

A good portion of the mansion has cathedral ceilings and windows acting as a modern derivative of church glass; there are even buttresses in the great room. The corners of large rooms near one of the seven fireplaces should get ample attention, too. The rooms are quite graceful for their size, and it’s all about material—wooden ceilings, wood-framed windows, glazed cherry cabinetry, and stone hearths. There are also two master suites, also with very high ceilings, and enchanting spaces to kick back or work out, namely the “Cheers” bar, billiards room, and indoor basketball court attached to the house.

The second owner decided to scale down in order to have homes downtown and on the North Shore and the third owner and current seller has scaled up in the region, believe it or not. All have been world travelers, so Ulbrich became the default caretaker over long stretches. 

Whoever buys the estate next will have to agree to leave the buffer of wooded acreage untouched. Those other two lots are developable, but the seller wants the rugged and secluded setting preserved.