Penthouses for Sale in Chicago, IL

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  /35

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  505 N Lake Shore Dr Unit 6801, Chicago, IL 60611

  Experience elevated city living in this truly one-of-a-kind penthouse residence offering approximately 3,000 square feet of impeccably designed living space. This exceptional 3-bedroom, 3-bathroom home showcases breathtaking panoramic views of Lake Michigan and the iconic Chicago skyline from every window, with coveted north and west exposures that deliver unforgettable sunsets. Designed with

  Denise Salazar Coldwell Banker Realty

  505 N Lake Shore Dr Unit 6801, Chicago, IL 60611
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  /30

  $1,295,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft

  1000 W Washington Blvd Unit 517, Chicago, IL 60607

  Another master craft, complete 2026 renovation by Twenty9, Inc., in the Heart of the West Loop at 1000 West. Residence 517 is a two story penthouse with a restored terra cotta ceiling, exposed brick, enormous metal girders and 28' private, recessed exposed brick terrace. Interior contemporary luxury features include 7" wide plank oak floors, 22' ceilings, 3 fully enclosed bedrooms and 3 full

  Nicholas Colagiovanni Baird & Warner

  1000 W Washington Blvd Unit 517, Chicago, IL 60607
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  /24

  $450,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  2236 N Maplewood Ave Unit 3, Chicago, IL 60647

  Freshly painted. Deep cleaned. Simply move in. Perched on the top floor of an intimate three-unit building, this sun-drenched two-bedroom two-bath lives large beneath soaring cathedral ceilings. Great views of the charming neighborhood pour in from front windows facing north, east, south and west, while rich hardwood floors run throughout an open, airy layout that flows straight back to your own

  Mary Ellen Apostolopoulos Compass

  2236 N Maplewood Ave Unit 3, Chicago, IL 60647
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  /36

  $2,995,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 3,430 Sq Ft

  416 W Deming Place Unit 4, Chicago, IL 60614

  Step into this one-of-a-kind East Lincoln Park penthouse, expertly designed by luxury lifestyle design group Soucie Horner, flooded with an abundance of natural light with custom features throughout. The open floor plan is not only an example of good design, but allows for high quality day-to-day living. Stepping through the private entrance expect to discover walls of glass/brick/stone, custom

  Jeffrey Lowe Compass

  416 W Deming Place Unit 4, Chicago, IL 60614
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  /27

  $745,000

  Open Sat 11:30AM - 1PM

  • 2 Beds
  • 2 Baths

  865 N Marshfield Ave Unit 3, Chicago, IL 60622

  Perfectly positioned on a quiet, tree-lined street in the heart of East Village, this exceptional penthouse blends sophisticated design with everyday livability. This home delivers the best of indoor-outdoor city living with 2 beds, 2 baths, a den perfect for a home office or workout space and two incredible private outdoor spaces. The sun-drenched main living space features oversized windows,

  Melanie Carlson @properties Christie's International Real Estate

  865 N Marshfield Ave Unit 3, Chicago, IL 60622
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  /24

  $675,000

  • 3 Beds
  • 2 Baths

  3414 N Sheffield Ave Unit 4, Chicago, IL 60657

  Beautiful 3-bedroom, 2-bath penthouse available in the heart of Wrigleyville. Enjoy exceptional outdoor living with two private outdoor spaces, including a spacious balcony off the living room and an expansive rooftop deck - perfect for entertaining, grilling, or taking in summer evenings above the city. Inside, the home's open-concept layout is enhanced by timeless architectural details,

  Karen Schwartz Baird & Warner

  3414 N Sheffield Ave Unit 4, Chicago, IL 60657
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  /37

  $1,299,900

  Pending

  • 6 Beds
  • 4.5 Baths
  • 4,900 Sq Ft

  2635 W Iowa St, Chicago, IL 60622

  Welcome to a masterpiece of modern luxury on a beautiful tree lined street in the heart of Chicago's vibrant West Town enclave. Boasting an expansive, custom designed 4900 square feet of interior living space, this extraordinary single family home offers a rare blend of grand scale entertaining, multi-generational flexibility, and unprecedented outdoor luxury. The main level serves as the

  John Parillo First Team Realty

  2635 W Iowa St, Chicago, IL 60622
• 

  

  /22

  $425,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,268 Sq Ft

  1225 W Morse Ave Unit 511, Chicago, IL 60626

  Top-floor penthouse corner unit with sunny south and east exposures, beautiful city views, and glimpses of Lake Michigan. Recently updated and completely move-in ready, this stylish home feels bright, open, and truly special. Soaring 12-foot ceilings, expansive windows, and clear views in multiple directions create an airy, modern atmosphere. Richly stained hardwood floors add warmth and contrast

  Santiago Valdez Compass

  1225 W Morse Ave Unit 511, Chicago, IL 60626
• 

  

  /22

  $799,999

  • 3 Beds
  • 3 Baths

  867 N Paulina St Unit 3S, Chicago, IL 60622

  Welcome home to this duplex-up penthouse on a tree-lined street in the East Village area of West Town. Step inside and immediately appreciate the two-story living room drenched in natural light, and open to your entertainer's kitchen with a wine fridge, lots of storage, and a large island great for guests. On the main floor you have a hall bath and bedroom with plenty of storage as well as your

  Caroline Kuby Baird & Warner

  867 N Paulina St Unit 3S, Chicago, IL 60622
• 

  

  /22

  $799,000

  New Construction Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,115 Sq Ft

  515 W Elm St Unit 502, Chicago, IL 60610

  BRAND NEW CONSTRUCTION, 2 bed/2 bath PENTHOUSE CONDO in a great part of Cabrini-Green. The expansive living area leads way to a gorgeous kitchen with high-end appliances and luxury finishes with a lovely deck off of the main living area. The primary suite includes a custom-built walk-in closet and en-suite bath, while the second bedroom offers flexibility as a guest room, home office, or nursery.

  William Goldberg Fulton Grace Realty

  515 W Elm St Unit 502, Chicago, IL 60610
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  /44

  $2,999,000

  • 3 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  333 W Hubbard St Unit 701, Chicago, IL 60654

  Some homes have outdoor space, this home has an outdoor lifestyle! A private escape above the city, this penthouse-level corner developer's residence offers approximately 3,200 square feet of beautifully renovated living space and nearly 1,800 square feet of extraordinary private outdoor living. Stretching an impressive 88 feet along the entire length of the home, the terrace is more than outdoor

  Carrie McCormick @properties Christie's International Real Estate

  333 W Hubbard St Unit 701, Chicago, IL 60654
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  /30

  $560,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  2427 W Augusta Blvd Unit 3, Chicago, IL 60622

  UKRAINIAN VILLAGE PENTHOUSE WITH ROOFTOP. Sexy, skyline views in this light-filled 2BR/2BA condo on coveted Augusta Blvd! Gated parking is included. Close to downtown, top-tier dining, and transit, the home boasts all-new windows (2025) and a complete roof rebuild-ready for you to build the private rooftop oasis of your dreams. Interior stairs lead to the roof, which runs the entire length of the

  Elizabeth Cavanaugh Captain Realty LLC

  2427 W Augusta Blvd Unit 3, Chicago, IL 60622
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  /32

  $650,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  1927 W Irving Park Rd Unit 4, Chicago, IL 60613

  Welcome home to your 3 BD/2BA North Center Penthouse Oasis! This extra-wide layout is well-designed, perfectly located and full of natural light. Spacious stainless steel kitchen boasts a large breakfast bar and granite tops adorn all counters. Combined living/dining room features a ventless fireplace and looks out to the first (of three) private balconies perfect for BBQ and lounging. Spa-like

  Jason Kilarski @properties Christie's International Real Estate

  1927 W Irving Park Rd Unit 4, Chicago, IL 60613
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  /65

  $7,100,000

  $400K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,734 Sq Ft

  363 E Wacker Dr Unit 9101, Chicago, IL 60601

  OWN THE ENTIRE 91ST FLOOR OF THE ST. REGIS CHICAGO! The highest customizable residence in Chicago and the Midwest and the only home in the building offering complete design freedom. Perched atop the iconic St. Regis Chicago, this extraordinary full-floor penthouse presents a once-in-a-lifetime opportunity to create a completely bespoke home in the sky. Spanning the entire 91st floor, this

  Laura England Compass

  363 E Wacker Dr Unit 9101, Chicago, IL 60601
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  /10

  $899,900

  • 3 Beds
  • 3 Baths

  6 S Laflin St Unit 907, Chicago, IL 60607

  Rarely available fully remodeled duplex penthouse in the heart of the West Loop. This stunning 3 bed, 3 bath home combines dramatic loft character with the comfort and functionality of a full-size home, offering over 2,300 square feet, soaring ceilings, oversized windows, and incredible natural light and skyline views throughout. The spacious duplex layout offers great flexibility for everyday

  Kinjal Shah Mark Allen Realty ERA Powered

  6 S Laflin St Unit 907, Chicago, IL 60607
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  /19

  $810,500

  $35K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft

  600 N Fairbanks Ct Unit 3307, Chicago, IL 60611

  This is the one buyers wait for-and miss if they hesitate. A rare southwest corner condo at 600 N Fairbanks Ct #3307 just hit the market, and the views alone are worth a visit. Floor-to-ceiling windows wrap the entire space, flooding it with light and delivering sweeping panoramic city views you won't get from most units. Step out onto your private balcony and you'll understand why this corner

  Jeffrey Sklar Beycome Brokerage Realty LLC

  600 N Fairbanks Ct Unit 3307, Chicago, IL 60611
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  /33

  $1,895,000

  Pending

  • 4 Beds
  • 3 Baths

  1905 N Bissell St Unit 3, Chicago, IL 60614

  One of Lincoln Park's most coveted streets, this extraordinary duplex-up Penthouse offers an unmatched combination of scale, luxury, and outdoor living in the heart of the sought-after Ranch Triangle. Thanks to incredibly rare RM-5.5 zoning, this residence boasts a significantly larger footprint than most homes in the neighborhood, delivering an expansive 4-bedroom, 3-bathroom floor plan with

  Steve Zaleski Compass

  1905 N Bissell St Unit 3, Chicago, IL 60614
• 

  

  /17

  $265,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  801 S Plymouth Ct Unit 1111, Chicago, IL 60605

  Rarely available Penthouse unit overlooking Sears Tower (Willis) and downtown Chicago. 2 large bedrooms, master has large walk-in closet and private full bath.The building features door staff, laundry room, storage lockers, bike storage, package receiving room, party room and on-site management office.located steps from the CTA Red Line, with easy access to Target, Jewel, Trader Joe's, Whole

  Qian Kun Chen Kale Realty

  801 S Plymouth Ct Unit 1111, Chicago, IL 60605

Showing Results 321 - 338, Page 9 of 9