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Rendering courtesy of 1000M, listing agent Lisa Chang Vitale of @properties

Chicago’s 25 most expensive homes for sale right now

See the blockbuster houses and condos on the market

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1000M.
| Rendering courtesy of 1000M, listing agent Lisa Chang Vitale of @properties

If you’re in the market for a luxury condo, you have a lot of options this year. Right now, sales for Vista Tower and 1000M dominate this high-end list and last year it was No. 9 Walton. Not surprisingly, there are also good amount of historic Gold Coast mansions, too. Lincoln Park’s Burling Street mansion tops the list, of course. But the neighborhood’s next listing? All the way down at number 19. Surprisingly, even with the West Loop being such a popular market, the neighborhood only appears once here. If you’re curious where Chicago’s richest residents could end up, these are the 25 most expensive homes for sale.

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1. 1926 N. Burling Street

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1926 N Burling St
Chicago, IL 60614

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.

Photos via listing agent R. Matt Leutheuser of Jameson Sotheby’s Intl Realty

2. 915 N. Dearborn Street

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915 N Dearborn St
Chicago, IL 60610

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.

Photos via Dawn McKenna of Coldwell Banker Residential Brokerage

3. 840 N. Lake Shore Drive, Unit 2601

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840 N Lake Shore Dr
Chicago, IL 60611

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.

Photo via listing agent Timothy Salm, Jameson Sotheby’s Intl Realty

4. Vista Tower Sky 360 Residences, Unit 8901

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345 E Wacker Dr
Chicago, IL 60601
(312) 620-8000
Visit Website

Listing price: $11,086,540

Here’s the priciest listing in Chicago’s third tallest building Vista Tower. You might have noticed the building under construction on Wacker, and when its finished, the skyscraper will be the first Chicago building to have a “blow through” floor.

Out of all the properties on this list, the Sky Residences have the latest and greatest amenities. Units are outfitted with Gaggenau appliances, Snaidero cabinetry, and Kallista fixtures. There are indoor and outdoor pools, fire pits, fitness and training rooms, private dining spaces, wine storage, and a dog exercise area.

Photo courtesy of Vista Tower, Leila Zammatta, Magellan Realty LLC

5. 199 E. Lake Shore Drive, Unit 10-11E

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199 E Lake Shore Dr
Chicago, IL 60611

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.

Photos by VHT Studios, courtesy of Engel & Völkers Chicago

6. 415 E. North Water Street, Penthouse 05

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415 E North Water St
Chicago, IL 60611

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.

Photos by ThreeSixty Chicago, courtesy of Grigory Pekarsky, Vesta Preferred LLC

7. 1000M Penthouse, Unit #71-PH1

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1000 S Michigan Ave
Chicago, IL 60605

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.

Photo by 1000M, courtesy of listing agent John Goldsworthy of @properties

8. 1325 N. Astor Street, Unit 13

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1325 N Astor St
Chicago, IL 60610

Listing price: $7,999,000

Astor Street is filled with opulent Chicago residences—and this one is available for the first time in 50 years. The duplex penthouse was designed by David Adler features original parquet floors and paneled walls from 1928. There are three terrace spaces, a marble stairway, and a dining room fit for 18 guests.

Photos by VHT Studios, courtesy of Nick Kluding of Baird & Warner

9. Vista Tower, Unit 6906

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345 E Wacker Dr
Chicago, IL 60601

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.

Photos by Vista Tower, courtesy of Leila Zammatta, Magellan Realty LLC

10. 1300 N. State Parkway

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1300 N State Pkwy
Chicago, IL 60610

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.

Photo courtesy of Mark Icuss at Compass

11. 1432 N. State Parkway

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1432 N State Pkwy
Chicago, IL 60610

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.

Photos courtesy of Jennifer Ames at Engel & Völkers Chicago

12. Vista Tower, Unit 5106

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345 E Wacker Dr
Chicago, IL 60601
(312) 620-8000
Visit Website

Listing price: $7,284,368

Surprise! It’s another condo in the pricey Vista Tower.

Photo courtesy of Vista Tower, Leila Zammatta, Magellan Realty LLC

13. Vista Tower, Unit 4806

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345 E Wacker Dr
Chicago, IL 60601
(312) 620-8000
Visit Website

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.

Photo courtesy of Vista Tower, Leila Zammatta, Magellan Realty LLC

14. 1246 N. Astor Street

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1246 N Astor St
Chicago, IL 60610

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.

Photos by Positive Image, courtesy of Jamie Ficco of Sergio & Banks Real Estate

15. 1421 N. Astor Street

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1421 N Astor St
Chicago, IL 60610

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.

Photo courtesy of Katherine Malkin of Compass

16. 1241 N. State Parkway

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1241 N State Pkwy
Chicago, IL 60610

Listing price: $6,495,000

This 7,4000-square-foot mansion is a brand new construction, which is less common in the historic Gold Coast district. It features a French limestone facade, an elevator, walk-in closets, rooftop terraces, and a backyard.

Photos courtesy of Tim Salm Jameson Sotheby’s International Realty

17. 1516 N. Lake Shore Drive

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1516 N Lake Shore Dr
Chicago, IL 60610

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.

Photos courtesy of Crystal Tran of Berkshire Hathaway HomeService

18. 65 E. Goethe Street, Unit M102

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65 E Goethe St
Chicago, IL 60610

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.

Photos courtesy of Sherri Kramer of Coldwell Banker Homes

19. 1919 N. Dayton Street

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1919 N Dayton St
Chicago, IL 60614

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.

Photo courtesy of Marie Campbell at Berkshire Hathaway HomeServices

20. 2450 N. Lakeview Avenue, Unit 10

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2450 N Lakeview Ave
Chicago, IL 60614

Listing price: $5,800,000

This Lincoln Park co-op sits on the 10th floor and directly faces Lincoln Park just 100 feet away. There’s a private elevator entrance, French hand-polished mahogany, a wine cellar, and a moody library. The building offers 24-hour door staff, a fenced-in courtyard, and a private garage.

Photo courtesy of Millie Rosenbloom at Baird & Warner

21. Palmolive Building, Unit 17AC

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159 E Walton Pl
Chicago, IL 60611

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.

Rendering courtesy of Katherine Malkin of Compass

22. 1000M, Unit 6802

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1000 S Michigan Ave
Chicago, IL 60605

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.

Rendering courtesy of 1000M, listing agent Lisa Chang Vitale of @properties

23. 132 E. Delaware Place, Unit 6302

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132 E Delaware Pl
Chicago, IL 60611

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.

Photo by Chicago Home Photos, courtesy of listing agent Klopas Stratton Berkshire Hathaway HomeServices

24. 900 W. Washington Boulevard, Penthouse 901

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900 W Washington Blvd
Chicago, IL 60607
(312) 867-2045
Visit Website

Listing price: $5,500,000

The lone West Loop home on this list arrives in a new building for the neighborhood called 900 West. The penthouse unit features 10-foot ceilings, expansive windows, heated floors, custom closets, and a wrap-around terrace. The building is also equipped with a biometric retinal scanner which residents will use for access.

Photo courtesy of Jameson Sotheby’s

25. 1433 N. State Parkway

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1433 N State Pkwy
Chicago, IL 60610

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.

Photo by VHT Studios, courtesy of Thomas Morrisey at Cedar Realty Group

1. 1926 N. Burling Street

1926 N Burling St, Chicago, IL 60614
Photos via listing agent R. Matt Leutheuser of Jameson Sotheby’s Intl Realty

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.

1926 N Burling St
Chicago, IL 60614

2. 915 N. Dearborn Street

915 N Dearborn St, Chicago, IL 60610
Photos via Dawn McKenna of Coldwell Banker Residential Brokerage

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.

915 N Dearborn St
Chicago, IL 60610

3. 840 N. Lake Shore Drive, Unit 2601

840 N Lake Shore Dr, Chicago, IL 60611
Photo via listing agent Timothy Salm, Jameson Sotheby’s Intl Realty

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.

840 N Lake Shore Dr
Chicago, IL 60611

4. Vista Tower Sky 360 Residences, Unit 8901

345 E Wacker Dr, Chicago, IL 60601
Photo courtesy of Vista Tower, Leila Zammatta, Magellan Realty LLC

Listing price: $11,086,540

Here’s the priciest listing in Chicago’s third tallest building Vista Tower. You might have noticed the building under construction on Wacker, and when its finished, the skyscraper will be the first Chicago building to have a “blow through” floor.

Out of all the properties on this list, the Sky Residences have the latest and greatest amenities. Units are outfitted with Gaggenau appliances, Snaidero cabinetry, and Kallista fixtures. There are indoor and outdoor pools, fire pits, fitness and training rooms, private dining spaces, wine storage, and a dog exercise area.

345 E Wacker Dr
Chicago, IL 60601

5. 199 E. Lake Shore Drive, Unit 10-11E

199 E Lake Shore Dr, Chicago, IL 60611
Photos by VHT Studios, courtesy of Engel & Völkers Chicago

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.

199 E Lake Shore Dr
Chicago, IL 60611

6. 415 E. North Water Street, Penthouse 05

415 E North Water St, Chicago, IL 60611
Photos by ThreeSixty Chicago, courtesy of Grigory Pekarsky, Vesta Preferred LLC

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.

415 E North Water St
Chicago, IL 60611

7. 1000M Penthouse, Unit #71-PH1

1000 S Michigan Ave, Chicago, IL 60605
Photo by 1000M, courtesy of listing agent John Goldsworthy of @properties

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.

1000 S Michigan Ave
Chicago, IL 60605

8. 1325 N. Astor Street, Unit 13

1325 N Astor St, Chicago, IL 60610
Photos by VHT Studios, courtesy of Nick Kluding of Baird & Warner

Listing price: $7,999,000

Astor Street is filled with opulent Chicago residences—and this one is available for the first time in 50 years. The duplex penthouse was designed by David Adler features original parquet floors and paneled walls from 1928. There are three terrace spaces, a marble stairway, and a dining room fit for 18 guests.

1325 N Astor St
Chicago, IL 60610

9. Vista Tower, Unit 6906

345 E Wacker Dr, Chicago, IL 60601
Photos by Vista Tower, courtesy of Leila Zammatta, Magellan Realty LLC

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.

345 E Wacker Dr
Chicago, IL 60601

10. 1300 N. State Parkway

1300 N State Pkwy, Chicago, IL 60610
Photo courtesy of Mark Icuss at Compass

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.

1300 N State Pkwy
Chicago, IL 60610

11. 1432 N. State Parkway

1432 N State Pkwy, Chicago, IL 60610
Photos courtesy of Jennifer Ames at Engel & Völkers Chicago

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.

1432 N State Pkwy
Chicago, IL 60610

12. Vista Tower, Unit 5106

345 E Wacker Dr, Chicago, IL 60601
Photo courtesy of Vista Tower, Leila Zammatta, Magellan Realty LLC

Listing price: $7,284,368

Surprise! It’s another condo in the pricey Vista Tower.

345 E Wacker Dr
Chicago, IL 60601

13. Vista Tower, Unit 4806

345 E Wacker Dr, Chicago, IL 60601
Photo courtesy of Vista Tower, Leila Zammatta, Magellan Realty LLC

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.

345 E Wacker Dr
Chicago, IL 60601

14. 1246 N. Astor Street

1246 N Astor St, Chicago, IL 60610
Photos by Positive Image, courtesy of Jamie Ficco of Sergio & Banks Real Estate

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.

1246 N Astor St
Chicago, IL 60610

15. 1421 N. Astor Street

1421 N Astor St, Chicago, IL 60610
Photo courtesy of Katherine Malkin of Compass

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.

1421 N Astor St
Chicago, IL 60610

16. 1241 N. State Parkway

1241 N State Pkwy, Chicago, IL 60610
Photos courtesy of Tim Salm Jameson Sotheby’s International Realty

Listing price: $6,495,000

This 7,4000-square-foot mansion is a brand new construction, which is less common in the historic Gold Coast district. It features a French limestone facade, an elevator, walk-in closets, rooftop terraces, and a backyard.

1241 N State Pkwy
Chicago, IL 60610

17. 1516 N. Lake Shore Drive

1516 N Lake Shore Dr, Chicago, IL 60610
Photos courtesy of Crystal Tran of Berkshire Hathaway HomeService

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.

1516 N Lake Shore Dr
Chicago, IL 60610

18. 65 E. Goethe Street, Unit M102

65 E Goethe St, Chicago, IL 60610
Photos courtesy of Sherri Kramer of Coldwell Banker Homes

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.

65 E Goethe St
Chicago, IL 60610

19. 1919 N. Dayton Street

1919 N Dayton St, Chicago, IL 60614
Photo courtesy of Marie Campbell at Berkshire Hathaway HomeServices

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.

1919 N Dayton St
Chicago, IL 60614

20. 2450 N. Lakeview Avenue, Unit 10

2450 N Lakeview Ave, Chicago, IL 60614
Photo courtesy of Millie Rosenbloom at Baird & Warner

Listing price: $5,800,000

This Lincoln Park co-op sits on the 10th floor and directly faces Lincoln Park just 100 feet away. There’s a private elevator entrance, French hand-polished mahogany, a wine cellar, and a moody library. The building offers 24-hour door staff, a fenced-in courtyard, and a private garage.

2450 N Lakeview Ave
Chicago, IL 60614

21. Palmolive Building, Unit 17AC

159 E Walton Pl, Chicago, IL 60611