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List Price: $6.499 million
The Property: Most people who talk about flipping a house don’t mean it quite as literally as Carole Segal does. At a Winnetka mansion she set out to restore and resell, Segal, who launched Crate & Barrel nearly 50 years ago with her husband, Gordon, flipped the front and back of the house. Visitors now approach the house via a long driveway that winds past big trees and a vast sweep of lawn, part of the estate’s 2.4 acres.

Inside the 10,000-square-foot house—built in 1936 by Ralph D. Huszagh, one of the architects of Uptown’s Aragon Ballroom—Segal’s touch is visible everywhere. But the expanded living room is a prime example of what she’s done. Beyond the new floor-length windows, the trees and lawns seem to envelop the room. “The room is infused with nature,” Segal said. “There are no curtains or drapes. This is the way I’ve always lived.”

Segal said that she and her husband had always loved the house and had been friendly with the couple who lived there for several decades. In 2005, that couple’s heirs sold to new owners who considered demolishing the house and splitting the acreage for two new homes. Their plans never went through, and in 2008, they sold the property to the Segals. “There were such good bones here,” Carole said. “I wanted to get it back to that, but make it work for a family who would live here today.”

To create the new kitchen, Segal and her architect, James Fraerman, combined three rooms into what she calls “the kitchen I’ve always wished I had.” It has a very large island, a chef-worthy appliance package, and lots of birch cabinetry. “You can never have enough storage in the kitchen,” Segal said. Next door is a dining room intended for family meals, outfitted with a fireplace and bench, birch paneling, and more full-length windows. There is also a large formal dining room.

Upstairs, Segal added a sitting room next to the master bedroom. The suite also has an enormous dressing room and a bathroom with floating vanities and striped-glass doors. There are three more bedrooms, each with its own bath, strung along the hall, and there’s also a library paneled in knotty pine.

A back stair leads back down to the kitchen and out to the big new family room, which Segal made from the old three-car garage. (There’s a new garage off to the side.) This space opens out via glass doors to a large walled garden, designed by Douglass Hoerr, where there used to be a driveway and car court. Here, beneath a towering shade tree, Segal told me that she is very pleased with the turnaround she accomplished here.

Price Points: The couple from whom the Segals bought the estate had paid $5.493 million for it in 2005, according to the Cook County Recorder of Deeds; they took an 18-percent loss when selling to the Segals in 2008. Carole Segal would not say how much the renovation cost. The rehabbed property first went on the market a year ago, with an asking price of $6.899 million; it went off the market later in the year and came back on at the current price in April.

Listing Agent: Eve Bremen of Coldwell Banker; 847-373-6091 or