The most expensive home currently listed in the sought-after North Shore suburb of Winnetka, Illinois, gives buyers the rare potential to own a pristine, private portion of land along Lake Michigan.
Listed at $14.9 million, 765 Sheridan Road offers more than 100 feet of lakefront space, with an in-ground pool, hot tub, full outdoor kitchen, three stone terraces, two decks, open space for entertaining, and a four-person tram that takes residents straight to the sandy beach.
“There’s a lot of flat tableland, which is unusual in Winnetka,” said listing agent Sharon Friedman of @properties Christie’s International Real Estate. “They’ve had many parties out there. The back of the house is very special.”
Inside, the 15,784-square-foot home offers amenities ideal for a family and “somebody that has a good pocketbook,” added Friedman.
The current homeowners purchased the lot in 2003 and spent two years constructing a custom home with details including Tiffany-designed glass doors and windows to hand-carved mahogany flooring on the ground level. The primary suite welcomes owners with custom curved French doors, a spa bath, a private sitting room and a balcony offering lake views.
“The owner of this home, this is their primary residence. They raised their family there,” said co-listing agent Courtney Cook of @properties Christie’s International Real Estate. “It’s a home with a nice family layout with all the modern conveniences that families want with, of course, a plethora of luxuries.”

The layout includes a large chef’s kitchen with panoramic views overlooking the lake and a Marc Chagall-inspired mosaic ceiling designed and mostly constructed in Europe, then installed in the home by artisans. A library includes one of the home’s five fireplaces. The souped-up basement has a theater, gym, golf simulator, full kitchen, second laundry room, massive rec room with access to the outdoors, and steam sauna.
Now downsizing, the homeowners have been looking to part with the seven-bedroom, eight-bathroom estate since August, when it was first listed at $18 million. It was reduced to $14.9 in mid-November, still remaining the priciest listing in Winnetka with a price per square foot of $944 and an estimated monthly payment of $100,334, according to Homes.com data. The median price of a single-family home in Winnetka is $1.83 million, and the average price per square foot is $504.

While the price makes it a unique Winnetka find, the lot makes it more special. The home sits on 1.3 acres, extending from Sheridan Road to the beach, and is surrounded by landscaping, creating much-desired privacy.
“Some of the other properties on the market now here are what we call flag lots. Your home is not visible or directly accessible; it’s behind another property,” Friedman said. “In the back of this home, you have no idea there’s a neighbor on either side.”
The home is close to Lloyd Park and the Stepan Family sailing beach, multiple parks and playgrounds. It’s also minutes away from numerous top-ranking schools.