Chicago’s Gold Coast, once a frog-invested swamp before Potter Palmer transformed it with landfill and built his famous 42-room castle, is now one of the city’s wealthiest neighborhoods. In the 1880s, Palmer convinced the city to build a seawall just north of Bellevue Place, which also created a relatively quiet boulevard next to his mansion. That’s right: Lake Shore Drive was originally used for carriage rides up to Lincoln Park. Not only did these improvements enhance the property values, but they attracted other affluent families to relocate here from Prairie Avenue and the South Side, which was becoming more congested and polluted from warehouses, factories, and the Illinois Central trains. It was said that Palmer only sold real estate to people he would have at his dinner table. Looking at the multi-million dollar prices in the Gold Coast today, it’s safe to say he would not decline an invitation to one of the following pricey pads. 

15 W Burton Pl, $11,988,000

The Gold Coast resident district is full of history on every block, whether the Catholic archbishop’s residence overlooking Lincoln Park or the seven houses designed by prestigious architectural firms that survive on Lake Shore Drive. But there are also newer structures, like this 10,000-square-foot limestone mansion constructed in 2008 that fits right into the exclusive neighborhood. With an almost $12 million price tag, it has everything you would expect in such a home: leather-paneled library, home theater, exercise studio, walk-in wine cellar, and elevator that services all four levels. But with winter coming, what really sells it to me is the heated three-car garage and the snow melt system embedded in the sidewalks. 

1443 N Astor St, $11,888,000

Frank Lloyd Wright’s first employer, architect Joseph Lyman Silsbee, designed this quarry-faced granite home for Horatio N. May in 1891. Located on Astor Street, the nearly 14,000-square-foot, six-bedroom, 12-bathroom mansion has original features like the grand reception room with marble flooring and adjacent cloak room. But there are modern luxuries like a primary bedroom suite that takes up the entire third floor, 17-seat home theater with stage and bar, two-story paneled billiard room, elevator that spans all five levels, and a heated two-car garage. Its oversized lot means there’s enough room for a beautiful slate patio and garden right outside the kitchen.

1336 N State Pkwy, $9,500,000

This past week there was a million-dollar price cut on the former wing of the original Playboy mansion where Hugh Hefner lived with his Playboy bunnies from 1959 until 1974. Between 2015 and 2020, the home went down from $14.5 to $10.5 million; today, it’s $9.5 million. Once 70 rooms, a developer converted the mansion into seven luxury condos in 1993 while the 9,000-square-foot wing became a completely separate residence. Originally built in 1914, it has been carefully renovated to mix classic elegance with modern amenities. There are vintage details like the grand staircase and decorative plaster ceilings, along with contemporary luxuries like a home theater, wet bar, exercise studio, elevator, and a penthouse garden with rooftop terrace and stunning views.

1521 N State Pkwy, $9,450,000

In 1895, George W. Maher designed this 9,700-square-foot Beaux-Arts limestone mansion for developer John L. Cochran, who later hired the architect to create a subdivision in the then suburb of Edgewater. Its facade made a brief appearance in the 2000 Mel Gibson-Helen Hunt flick What Women Want. The interior was gut renovated and features a modern open floor plan with advanced Creston-Lutron technology and state-of-the-art mechanical systems. There are three multi-level outdoor spaces including a roof deck with fireplace, built-in grill, and beautiful landscaping. Plus the home comes with two parking spaces — essential in a congested area like this one.