When the current owner of 445 Sheridan Road in Winnetka first walked up the stairs to this home, his breath was taken away by the majestic views of Lake Michigan.

“My client told me a story just this morning,” Jena Radnay of @properties Christie’s International Real Estate shares. “He said he knew the minute he walked into the foyer of this home and saw the lake that he felt like he had ‘arrived.’ He knew he had to have this house.”

This Winnetka estate has long been one of which stories have been told—stories of self-made millionaires whose successes were celebrated within the gates of this iconic residence.

“If you grew up in Winnetka, you knew this house as the one with the gates and the red tile roof. It’s a rarity for an estate like this to have an ‘in-town location’ with lakefront access,” Radnay says.

Built in 1912, this Spanish-influenced villa is glorious and reminiscent of a time when entertaining on Lake Michigan was a true way of life. This home has only had four homeowners to date—W. Clement Stone being the most notable. When he purchased the property in early 1966, Stone had garnered success with the founding of Combined Insurance Company (now Aon Corporation). Born into poverty on Chicago’s South Side in 1902, Stone started his own insurance agency at the age of 20, and within a decade, his company had 1,000 agents selling low-cost policies throughout the country.

The Stones extensively renovated and lavishly decorated the house and were known for the parties they hosted. According to the Winnetka Historical Society, one such party was described as having “a sit-down dinner on the first floor, champagne on the second, and dancing to two bands in the third-floor ballroom.”

When arriving at the Stones’ glamorous fetes, guests were greeted by the grand foyer entrance with postcard views of the lake, a double atrium staircase accented with braided columns, matching arched casings, and a fireplace. The sunrises, sunsets, and lakefront breezes only added to the magic.

Stone and his wife, Jessie, both lived to age 100 and died on the same day two years apart. The house went on the market a few months later and was sold in 2006 to its current owners. These homeowners worked with architect Paul Konstant to improve the property while maintaining its historic character.

Almost all of the rooms in this home face the water allowing for incredible natural light from the lakefront’s reflections. Formal spaces on the first floor provide the ideal flow for entertaining. The grand living room has 10-foot ceilings and curved corners with built-in areas to display treasures. The family room, with more panoramic views, follows. An enchanting dining room with an intricate hand-molded ceiling, five chandeliers, and a separate solarium breakfast area create areas for formal and informal dining.

The recently renovated second floor has a primary suite side with a sitting room, walk-in closet, spa bath, and bedroom with 180-degree views of the lake. Three additional bedrooms with new quartz baths are also found on the second floor. The formal ballroom with its own exquisite lake views is still on the third floor. An elevator connects the floors—including the Hollywood-esque speakeasy on the lower level. If these walls could only talk, those stories would write a book about the custom bar, booths made for lounging, and custom-plastered mosaic ceilings with hand-painted and mirrored tiles. The oversized recreation room, home to a billiards area, sauna, and full bath, is just what you would expect in a home of this stature.

While the current homeowners worked with Konstant on restoring the home, their most prized collaboration was the cabana and hotel-level pool experience they created in the front yard.

“This is such a special part of this property,” adds Radnay. “This four-season, commercial-sized pool was built in front of the home to protect it from the cool lake breezes so that it can be enjoyed all year long. The construction has been grandfathered into the zoning laws of the Village of Winnetka and can never be replicated anywhere else.”

The Konstant-designed two-story cabana house features an elevator, a custom bar with mahogany-coffered wooden ceilings, two full kitchens, two bedrooms, and two full bathrooms. A stunning fountain adds the finishing touch and creates the most peaceful and tranquil of settings.

“While this home is historically significant to our community, it is not bound by any preservation restrictions,” Radnay explains. “This means that someone can come in and modernize the living space to how families live today or create something entirely new. There are only a handful of lakefront properties like this with acreage of this size.”

To this end, Konstant has already drawn up plans for how this home could be reimagined. And, the new homeowners will have this architect’s expertise close at hand as he lives just down the street.

“This home was built for dreamers,” Radnay adds. “Some of our city’s most successful entrepreneurs have lived here—individuals who dreamed big and found incredible success. This is the kind of person who will make this luxurious estate their home.”

To learn more about this property, visit atproperties.com or contact Jena Radnay at 312-925-9899.