Listing price: $45 million

This Lincoln Park mansion has been the city’s most expensive property since it first listed in 2016. Back then, it was $50 million. But still, even after cutting back $5 million it tops the list.

The 25,000-square-foot estate was built on eight city lots and comes with ornate fountains, a reflecting pool, chandeliers, a curving grand staircase, marble inlays, and manicured gardens.

Listing price: $19,500,000

Last sold in 2009 for $3,128,000, this Gold Coast mansion has gone through a high-end restoration. The red rock home was originally built for an attorney in 1888 and based on designs by architecture firm Cobb and Frost. The firm is known for now-demolished buildings like the Palmer Mansion and the Chicago Opera House.

The residence has highly detailed woodwork, art glass windows, Santos Mahogany hardwood, carved marble fireplaces, and a carriage house.

Listing price: $13,500,000

This Lake Shore Drive building holds the first condo on our list. It was built in 2007, and as a full-floor penthouse unit, boasts some of the best skyline views. The nearly 10,000-square-foot residence has 12-foot ceilings, a massive terrace, a rotunda living room, and a dream kitchen.

Listing price: $11,500,000

Designed by Benjamin Marshall, this 9,600-square-foot home is one the market for the first time in 25 years. The listing description says the home is perfect for “Gatsby style entertaining.” There’s a grand, wood-paneled room with a pool table, a spacious kitchen with its own fireplace, an elegant dining room, skylights, and a conservatory attached to a large terrace.

Listing price: $8,990,000

This two-story penthouse is from the early 2000s era when marble-covered everything, giant aquariums, and full-length basketball courts were the epitome of luxury. While trends have shifted since, the property still has potential: a wrap-around terrace, impressive views over the Chicago River and Lake Michigan, and a master suite with a custom walk-in closet.

Listing price: $8,100,000

Still under construction, this project is another highly anticipated skyscraper. Designed by architect Helmut Jahn and interior designer Kara Mann, 1000M is expected to partially open mid-2022.

A few of the amenities in this prestigious project? There’s a music conservatory, gardens, a sprawling terrace, and a spa with a Himalayan salt room. The penthouse unit has quite an impressive interior with a luxurious bathroom.

Listing price: $7,887,000

Vista Tower makes another appearance on this list. These condos are below the Sky 360 Penthouses, but still offer the same panoramic views. This unit is 5,261 square feet and comes with four ensuite bedrooms, his and her master bathrooms, and a 32-foot long terrace.

Listing price: $7,850,000

Striking out on its own, this condo has the most contemporary style on this list. It was purchased as a raw space and designed by architects at Wheeler Kearns. One of the home’s most unique features is the Venetian plaster-wrapped staircase with rounded edges. The home side steps a traditional luxury aesthetic—there’s no wood panels or ornately carved fireplaces. Instead, a smooth concrete fireplace, bright modern art, and busy fabric patterns.

Listing price: $7,499,000

Just down the street is another Gold Coast mansion that makes the list. The 9,100-square foot, double lot property features some of the home’s original details from 1883. There’s a marble bathroom, a full-floor master bedroom, a guest suite in the coach house, and a landscaped side yard.

Listing price: $7,231,516

In case it wasn’t clear, Vista Tower will be home to all of Chicago’s millionaires when it opens later this year. This is the building’s fourth unit on this list.

Listing price: $6,999,000

Built in 1886, this Gold Coast mansion features a completely renovated interior. Led by Axios Architects and Lisek Interiors, this corner lot home comes with an elevator, a rooftop deck with fireplaces, and a steam room.

Listing price: $6,800,000

Here’s another historic Astor Street mansion. It was first built in 1892 and retains several original architectural details like a Gothic fireplace in limestone, walnut paneling, bronze sconces, and leaded glass windows. It’s also got a gated driveway from the curb up to the four-car garage.

Listing price: $6,000,000

This Lake Shore Drive mansion was used at the offices for the International College of Surgeons, and now the 12,000-square-foot main house and its 2,400-square-foot coach house are on the market. Built in 1916, the property is both a Chicago Landmark and listed on the National Register of Historic Places.

To truly turn this space into a home, the property will need an extensive renovation. The good news for buyers with deep pockets is that it appears original flooring and millwork have been maintained.

Listing price: $5,989,000

Here’s a newer Gold Coast boutique condo. Built in 2011, the property only has 18 units. This home has a dramatic entry foyer with 11-foot ceilings and 5,800-square feet of space spread across two floors. The kitchen was designed by de Giulio and opens up to a private 1,300-square-foot terrace.

Listing price: $5,950,000

This double lot mansion is the first Lincoln Park residence to show up on the list. A few years ago, the neighborhood would have been much closer to the top of this list. Now with Vista Tower and 1000M dominating the luxury market, things have changed.

Built in 2011, this property features everything you’d expect in a multi-million dollar home: an elevator, French doors, and gold chandeliers. There’s a fireplace in the master bedroom (and four others throughout the house), a movie theater with loungers, a stately wood-paneled library, and a private terrace.

Listing price: $5,750,000

Formerly the editorial offices of Playboy, this 37-story Art Deco building is known as the Palmolive now. This is also where Vince Vaughn once owned a multi-floor penthouse—it sold in 2016. While not as dramatic as Vaughn’s penthouse, this unit has the same stunning views. It comes with coved ceilings, a wood-paneled library, and elegant fireplaces. The listing price also includes two garage spaces.

Listing price: $5,650,000

This is 1000M’s second listing on the list. For a few million less, you can also live in the Helmut Jahn-designed skyscraper in a 4,104-square-foot unit and take advantage of that Himalayan salt room down in the spa.

Listing price: $5,600,000

This duplex residence in a Gold Coast tower has airy 20-foot ceilings and walls of windows. Plus, it’s located in the Four Seasons Hotel so you’ll enjoy all of its amenities. There are artisanal finishes, custom millwork, and a unique view of Lake Michigan and the Hancock Tower.

Listing price: $5,499,000

Finally, we end with a Gold Coast mansion that underwent a complete rehab in 2011. It features a few interesting rooms including one outfitted in like a rugged hunting lodge with stained wood and an antler chandelier. There’s also a 300-bottle wine cellar, elevator, nine fireplaces, and an audio system through the whole house.