Penthouses for Sale in Chicago, IL

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  /12

  $759,000

  New Construction Pending

  • 3 Beds
  • 2 Baths

  805 N California Ave Unit 402, Chicago, IL 60622

  Come embrace this first look opportunity to obtain the finest! Welcome to 805 North California! A premier, luxury, new-construction condominium development showcasing nine fabulous homes! Buyers will enjoy the luxury and convenience of an ELEVATOR building with ATTACHED garage parking INCLUDED! EV capabilities offered. CONCRETE between floors for enhanced sound insulation! This is truly a

  Karen Biazar North Clybourn Group, Inc.

  805 N California Ave Unit 402, Chicago, IL 60622
• 

  

  

  /22

  $725,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,522 Sq Ft

  1226 W Winnemac Ave Unit 3S, Chicago, IL 60640

  Modern, light-filled 2-bedroom penthouse in a beautiful historic Chicago greystone, tucked onto a quiet residential street in one of the city's most vibrant neighborhoods. Fully updated in 2021, this home blends contemporary style and convenience with the architectural character of the original building. The south-facing main living space is bathed in incredible natural light and features

  Scott Berg Berg Properties

  1226 W Winnemac Ave Unit 3S, Chicago, IL 60640
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  /39

  $1,475,000

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft

  10 E Ontario St Unit 500102, Chicago, IL 60611

  Experience elevated city living in River North with this stunning penthouse-level 3-bedroom, 3-bathroom combined condo featuring a thoughtfully designed layout with two spacious primary suites (and two walk-in closets), perfect for comfort and flexibility. This exceptional residence boasts heated floors throughout, a working electric fireplace for those cold winter nights, and a fully renovated,

  Stefanie Krause Corcoran Urban Real Estate

  10 E Ontario St Unit 500102, Chicago, IL 60611
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  /27

  $800,000

  • 2 Beds
  • 3 Baths
  • 2,696 Sq Ft

  40 E Delaware Place Unit 1702, Chicago, IL 60611

  Rarely available 2-bedroom penthouse residence in an intimate boutique building on one of the Gold Coast's most coveted corners. This spacious home blends vintage charm with modern updates and offers an exceptional layout for both everyday living and entertaining. The updated kitchen features custom cabinetry, stone countertops, and high-end stainless steel appliances, opening seamlessly to the

  John Floros Fulton Grace Realty

  40 E Delaware Place Unit 1702, Chicago, IL 60611
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  /26

  $1,400,000

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

  420 W Grand Ave Unit 5D, Chicago, IL 60654

  Experience the pinnacle of urban luxury in this rare, 2,500-square-foot River North penthouse loft, where 14-foot timber ceilings and exposed brick meet unparalleled modern sophistication. Designed for the ultimate entertainer, the home features a stunning, recently redesigned chef's kitchen boasting custom Italian cabinetry, exquisite quartzite counters and backsplash, a SubZero refrigerator,

  Danielle Dowell Berkshire Hathaway HomeServices Chicago

  420 W Grand Ave Unit 5D, Chicago, IL 60654
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  /37

  $299,990

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  30 E Huron St Unit 5605, Chicago, IL 60611

  Perched on the 56th floor, this rare penthouse offers the ultimate River North lifestyle with breathtaking, unobstructed city views from the very top of the building. This custom-upgraded 1 bedroom, 1 bath unit has been beautifully refreshed with brand new flooring, fresh paint throughout, and automatic blinds - move-in ready and dialed in for effortless city living. The custom kitchen features

  Nicholas Chiaramonte Northwest Real Estate Group

  30 E Huron St Unit 5605, Chicago, IL 60611
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  /37

  $474,900

  Pending

  • 2 Beds
  • 1 Bath

  4170 N Marine Dr Unit 24H, Chicago, IL 60613

  Welcome to luxurious lakefront living in this penthouse unit. Enjoy the best of the best at The Waterford condominium building, in historic Buena Park (East Lakeview). This 24th floor penthouse has been meticulously gut rehabbed using high quality craftsmanship and top of the line finishes. The two bedroom unit features a redesigned floorpan which maximizes use of the space, creating bright open

  Eamonn Stafford @properties Christie's International Real Estate

  4170 N Marine Dr Unit 24H, Chicago, IL 60613
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  /42

  $2,250,000

  • 4 Beds
  • 3.5 Baths
  • 3,080 Sq Ft

  530 W Dickens Ave Unit 401, Chicago, IL 60614

  Perched atop an intimate boutique elevator building clearing most of the charming homes below, in one of Lincoln Park's most coveted locations, this extraordinary duplex penthouse occupies the entire top two floors. Offering an unparalleled level of privacy, unbelievable 360-degree skyline and Lincoln Park views with exceptional natural light from every exposure thing this is a one of a kind home

  Emily Sachs Wong @properties Christie's International Real Estate

  530 W Dickens Ave Unit 401, Chicago, IL 60614
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  /66

  $9,500,000

  • 5 Beds
  • 7 Baths
  • 7,700 Sq Ft

  175 E Delaware Place Unit 9210, Chicago, IL 60611

  Introducing one of Chicago's most extraordinary trophy penthouse residences, a remarkable 92nd-floor home in the legendary John Hancock Center commanding uninterrupted 360-degree views of Lake Michigan, the skyline, and beyond. There is simply no other home in Chicago like this. Rising 1,010 feet above Michigan Avenue within one of the world's most architecturally significant buildings,

  Carrie McCormick @properties Christie's International Real Estate

  175 E Delaware Place Unit 9210, Chicago, IL 60611
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  /28

  $484,900

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  100 E 14th St Unit 1209, Chicago, IL 60605

  Enjoy Exceptional City Living just steps from Chicago's Lakefront, Millennium Park, Grant Park, and the Museum Campus in this spacious 2/Bedroom, 2/Bath residence with a Home Office at 1400 Museum Park. Offering approximately 1300 square feet of thoughtfully designed living space, this Home Combines Comfort, functionality, and Convenience with a Private Balcony and Access to Outstanding

  Sonya Lea Berkshire Hathaway HomeServices Chicago

  100 E 14th St Unit 1209, Chicago, IL 60605
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  /31

  $2,950,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,013 Sq Ft

  211 N Harbor Dr Unit 4301, Chicago, IL 60601

  SOLD BEFORE PRINT. Experience luxury resort-style lakefront living at Cirrus in the exclusive Lakeshore East neighborhood with its premier amenities, prime location and private community. Set among Lakeshore East's serene green spaces where the Chicago River meets Lake Michigan, Cirrus offers its residents easy access to the lakefront running and biking path, DuSable Harbor and adjacent

  Brad Brondyke Jameson Sotheby's Intl Realty

  211 N Harbor Dr Unit 4301, Chicago, IL 60601
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  /46

  $2,050,000

  $50K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 2,400 Sq Ft

  401 N Wabash Ave Unit 86B, Chicago, IL 60611

  Rarely available 86th-floor penthouse residence offering breathtaking panoramic views from one of Chicago's most iconic towers, designed by renowned architect Adrian Smith of Skidmore, Owings & Merrill. This exclusive floor features enhanced ceiling heights and private restricted access reserved for 86th-floor residents only. The home showcases exceptional designer finishes throughout, including

  Chezi Rafaeli Coldwell Banker Realty

  401 N Wabash Ave Unit 86B, Chicago, IL 60611
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  /71

  $3,425,000

  New Construction

  • 8 Beds
  • 8 Baths

  3739 N Clifton Ave, Chicago, IL 60613

  A rare opportunity to own an entire brand-new luxury building in the heart of Lakeview, offering exceptional flexibility for investors, multi-generational living, owner-occupants, or those seeking a long-term wealth-building opportunity. Comprised of three beautifully finished residences, this boutique property offers endless possibilities from creating a private family compound to generating

  Carrie McCormick @properties Christie's International Real Estate

  3739 N Clifton Ave, Chicago, IL 60613
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  /34

  $2,600,000

  • 4 Beds
  • 3 Baths
  • 3,437 Sq Ft

  225 N Columbus Dr Unit 8006, Chicago, IL 60601

  Penthouse Level-Outdoor Space: Experience breathtaking views of the lake and city from an 80th-floor penthouse in Chicago's iconic Aqua Tower. Designed by award-winning architect Jeanne Gang, the building features distinctive, gently rippling balconies that give the skyscraper its signature sculptural form. This deluxe penthouse in Chicago's Lakeshore East - New Eastside rises to the 80th floor,

  Alexis Eldorrado Eldorrado Chicago Real Estate

  225 N Columbus Dr Unit 8006, Chicago, IL 60601
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  /10

  $114,900

  • 1 Bed
  • 1 Bath
  • 712 Sq Ft

  6700 S South Shore Dr Unit 12E, Chicago, IL 60649

  Discover this beautiful 1-bedroom, 1-bath 12th floor condo in the historic Jackson Park Highlands neighborhood! The unit features a spacious living room with an open layout and tons of natural light. The kitchen is efficiently arranged and equipped with stainless steel appliances, while the large bedroom includes a walk-in closet for ample storage. The bathroom was rehabbed in 2022 and offers

  Marcus Mason Baird & Warner

  6700 S South Shore Dr Unit 12E, Chicago, IL 60649
• 

  

  /23

  $1,149,000

  New Construction

  • 3 Beds
  • 2.5 Baths

  2023 W Augusta Blvd Unit 3W, Chicago, IL 60622

  We are excited to introduce 2023 W Augusta, Ukrainian Villages newest boutique luxury development. Built by highly experienced developers, this five unit building sits on an extra wide 48 foot lot, providing expansive floor-plans and exceptional natural light. Penthouse homes consist of Three large bedrooms and 2 1/2 bathrooms with fully finished private roof decks with city and skyline views.

  James Sheehan Meridian Real Estate Chicago LLC

  2023 W Augusta Blvd Unit 3W, Chicago, IL 60622
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  /40

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,261 Sq Ft

  3024 W Irving Park Rd Unit 3S, Chicago, IL 60618

  Live like you're in a single-family home in this exceptional newer-construction Irving Park duplex penthouse, offering three bedrooms, two-and-a-half baths, two beautifully designed interior levels, and a private rooftop retreat that creates a remarkable third level of living beneath the Chicago skyline. Bathed in natural light from oversized windows and enhanced by soaring 10-foot ceilings, the

  Nicole Carrizalez Compass

  3024 W Irving Park Rd Unit 3S, Chicago, IL 60618
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  /12

  $275,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,450 Sq Ft

  1033 E 46th St Unit 406, Chicago, IL 60653

  Welcome to this sun-filled penthouse residence, perfectly positioned within the highly sought-after, gated Shakespeare Court community. This spacious 2-bedroom, 2-bath condo offers an inviting blend of comfort, style, and convenience. Refinished hardwood floors flow throughout the home, while the open-concept living and dining area is anchored by a cozy gas fireplace. The well-appointed kitchen

  Sharial Howard @properties Christie's International Real Estate

  1033 E 46th St Unit 406, Chicago, IL 60653
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  /34

  $724,995

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  545 N Dearborn St Unit W3301, Chicago, IL 60654

  A stunning penthouse-level gem located in Chicago's highly desirable River North neighborhood. Boasting a complete 2024 renovation, this impeccable corner unit offers elegant living with high ceilings, a gracious formal entry, sleek hardwood flooring, expansive 175 sq ft balcony and breathtaking high floor city views. Other remarkable features include a large, light-filled living area, floor to

  Stefanie Lavelle @properties Christie's International Real Estate

  545 N Dearborn St Unit W3301, Chicago, IL 60654
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  /32

  $575,000

  New Construction

  • 3 Beds
  • 2.5 Baths

  6414 N Francisco Ave Unit 202, Chicago, IL 60645

  This top floor residence is a brand-new 3-bedroom, 2.5-bathroom, duplex-up penthouse designed for modern living and effortless entertaining. All bedrooms are thoughtfully located on the upper level, creating a private retreat, while the main level is dedicated to entertaining with an open, airy layout on a wide lot. The home is filled with tons of natural light and features luxury modern finishes

  Joel Halperin Compass

  6414 N Francisco Ave Unit 202, Chicago, IL 60645
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  /16

  $975,000

  3241 S Carpenter St, Chicago, IL 60608

  Prime Bridgeport investment opportunity! Well-maintained six-unit property featuring all 2-bedroom apartments, including two garden units and a 2-bed/2-bath duplex-up penthouse. Top-floor units offer in-unit laundry and dishwashers. Highlights include individual HVAC and water heaters, separately metered utilities, vinyl windows, a recently replaced wood porch system, and a two-car garage with

  Adam Max Compass

  3241 S Carpenter St, Chicago, IL 60608
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  /18

  $169,900

  • Studio
  • 1 Bath

  4343 N Clarendon Ave Unit 2801, Chicago, IL 60613

  Welcome to Unit 2801 at 4343 N Clarendon Avenue, a bright, spacious penthouse studio offering impressive south facing 28th-floor views of downtown and the lake in the heart of Buena Park. This well-designed home features an open living and sleeping area, a functional kitchen, a full bathroom, generous closet space, and central heating and air conditioning. Enjoy full-service building amenities,

  Daniel Ledo RE/MAX Premier

  4343 N Clarendon Ave Unit 2801, Chicago, IL 60613
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  /54

  $2,897,747

  • 4 Beds
  • 3.5 Baths
  • 3,320 Sq Ft

  180 E Pearson St Unit 7203, Chicago, IL 60611

  PENTHOUSE LEVEL, 72nd Floor, 4-bedroom, NORTHEAST corner, 3320 square foot floor plan at the luxurious Water Tower Residences featuring impressive, sweeping lake, park and city views framing Navy Pier to the East exposure and up to Evanston along the Lake Michigan shoreline to the North exposure. The lake seems more like an Ocean through the 24 oversized windows with motorized shades. Your

  Michael Rosenblum Berkshire Hathaway HomeServices Chicago

  180 E Pearson St Unit 7203, Chicago, IL 60611
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  /56

  $1,499,000

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

  910 W Madison St Unit 904E, Chicago, IL 60607

  Idyllic and centrally located in the heart of the West Loop, this luxurious 3 bed | 3 bath penthouse loft combines two units into one stunning residence with high-end finishes and an unmatched outdoor retreat: a private, 1,500 square foot wraparound terrace with professional landscaping. The home's modern layout begins with a dramatic foyer featuring Italian marble tile and custom backlit walnut

  Collin Wasiak Compass

  910 W Madison St Unit 904E, Chicago, IL 60607
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  /33

  $950,000

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  2507 N Halsted St Unit 4, Chicago, IL 60614

  Top-floor 3-bedroom, 2-bath penthouse in the heart of Lincoln Park, featuring a newly completed 1,900 sq ft private rooftop with stunning skyline views. This sun-filled home features an open-concept kitchen with granite countertops, walnut hardwood floors throughout, and 10+ ft ceilings with crown molding and wainscoting. Additional highlights include two parking spaces, in-unit washer/dryer, two

  Danielle Dowell Berkshire Hathaway HomeServices Chicago

  2507 N Halsted St Unit 4, Chicago, IL 60614
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  /20

  $1,900,000

  • 4 Beds
  • 3.5 Baths
  • 2,579 Sq Ft

  1629 N Burling St Unit 3, Chicago, IL 60614

  This stunning 4-bedroom, 3.1-bathroom duplex penthouse in the heart of Lincoln Park has a thoughtfully designed floor plan, refined finishes, and exceptional indoor/outdoor living. The main level is designed for daily living and effortless entertaining with an expansive living and dining space that opens seamlessly to a covered terrace. The chef's kitchen is appointed with custom cabinetry,

  Ryan Preuett Jameson Sotheby's Intl Realty

  1629 N Burling St Unit 3, Chicago, IL 60614
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  /32

  $335,000

  Pending

  • 1 Bed
  • 1 Bath
  • 820 Sq Ft

  1355 N Sandburg Terrace Unit 2902D, Chicago, IL 60610

  Perched on the top floor, this penthouse southeast corner residence offers breathtaking, unobstructed views of the Gold Coast, downtown skyline, and Lake Michigan. This spacious one-bedroom plus den/home office is move-in ready and perfectly situated between the Gold Coast and Old Town. The bright, open living space features hardwood floors, while the updated kitchen is appointed with granite

  Maggie Ahern @properties Christie's International Real Estate

  1355 N Sandburg Terrace Unit 2902D, Chicago, IL 60610
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  /24

  $615,000

  Pending

  • 2 Beds
  • 2 Baths

  503 N Wells St Unit 3, Chicago, IL 60654

  Manhattan Style Penthouse Loft in an intimate walk up building! This show stopper is perched above the heart of River North and all it has to offer. Flooded with natural light, 14 foot ceilings and multiple skylights. Exposed brick, strategically featured glassblock and dark hardwood floors flow throughout creating an airy, inviting environment. The open kitchen is perfectly situated for

  Michael Scanlon eXp Realty

  503 N Wells St Unit 3, Chicago, IL 60654
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  /27

  $775,000

  New Construction Pending

  • 3 Beds
  • 3 Baths
  • 2,350 Sq Ft

  6218 S Woodlawn Ave Unit A, Chicago, IL 60637

  Ultra-contemporary new construction corner residences within a gated 14-home community, designed to elevate daily living while maintaining effortless sophistication. These striking homes feature heated floors-polished concrete or engineered white oak-solid-core flat-panel doors, LED lighting, tall ceilings, and an attached two-car garage. The dramatic two-story main level is anchored by a

  Michelle Browne @properties Christie's International Real Estate

  6218 S Woodlawn Ave Unit A, Chicago, IL 60637
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  /48

  $995,000

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  4249 N Kolmar Ave, Chicago, IL 60641

  Enjoy maintenance-free living in the largest Single Family model of The Terrances of Old Irving Park! Nestled in a secure cul-de-sac, this newly renovated 5BR 4.5BA 4000+ sf hidden oasis features open floor plan with formal living, formal dining, granite black-SS kitchen with eat-in island and breakfast area, generous family room with gas fireplace and a large barbecue deck overlooking a private

  Alix Jung Xi Zhang

  4249 N Kolmar Ave, Chicago, IL 60641
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  /40

  $950,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,727 Sq Ft

  1601 S Indiana Ave Unit 503, Chicago, IL 60616

  Spectacular penthouse duplex loft with stunning, skyline views in the heart of Chicago's vivacious South Loop neighborhood! Gut rehabbed in 2017, the owners reimagined the space, creating a home that is as vibrant as it is chic. Upon entry, an elevated entry foyer highlights the soaring, 14 ft timber beamed ceilings. A few steps down into the living space, exposed brick, an open floor plan,

  Carrie McCormick @properties Christie's International Real Estate

  1601 S Indiana Ave Unit 503, Chicago, IL 60616
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  /52

  $10,995,000

  • 4 Beds
  • 4.5 Baths
  • 5,890 Sq Ft

  363 E Wacker Dr Unit 7601, Chicago, IL 60601

  A full-floor penthouse of rare distinction, this residence at The St. Regis Chicago has been completely reimagined and elevated beyond its original delivery, emerging as a truly one-of-one offering within the Chicago market. Framed by sweeping 360-degree views, every room is immersed in a cinematic panorama of Lake Michigan, Navy Pier, Monroe Harbor, and the ever-evolving skyline-an uninterrupted

  Rafael Murillo Compass

  363 E Wacker Dr Unit 7601, Chicago, IL 60601
• 

  

  /23

  $799,900

  Pending

  • 3 Beds
  • 2 Baths

  1319 N Wood St Unit 3C, Chicago, IL 60622

  Experience the best of Wicker Park living in this exceptional penthouse duplex-up located in a desirable elevator building. Unlike a typical duplex layout, this home offers a spacious, open-concept main level with soaring ceilings and dramatic floor-to-ceiling windows that fill the space with natural light. The main floor features a generous living room, a separate dining area, a beautifully

  Sue Hall @properties Christie's International Real Estate

  1319 N Wood St Unit 3C, Chicago, IL 60622
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  /2

  $899,000

  Pending

  • 3 Beds
  • 2 Baths

  3823 N Ashland Ave Unit 503, Chicago, IL 60613

  Sold before print

  Dave Gould @properties Christie's International Real Estate

  3823 N Ashland Ave Unit 503, Chicago, IL 60613
• 

  

  /22

  $950,000

  • 3 Beds
  • 2 Baths

  3306 N Clifton Ave Unit 3N, Chicago, IL 60657

  Rarely available Lakeview duplex penthouse with two private outdoor spaces including an incredible private rooftop deck with skyline and sunset views. This is anything but a cookie-cutter condo, with a distinctive, collected feel and a flexible floor plan that lives more like a home. The main level features hardwood floors throughout and a open floor plan with a gas fireplace and windows on

  Vikas Wadhwa Urban Living Properties, LLC

  3306 N Clifton Ave Unit 3N, Chicago, IL 60657
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  /42

  $1,299,900

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft

  550 N Kingsbury St Unit 610, Chicago, IL 60654

  Experience a truly one of a kind penthouse duplex loft in the heart of River North! Spanning over 2,450 square feet, this 4 bedroom, 3 bath residence seamlessly blends authentic loft character with thoughtfully curated, high-end updates. The main level is anchored by soaring timber ceilings, expansive windows, and an impressive open concept living and dining space designed for both everyday

  Kaylin Goldstein @properties Christie's International Real Estate

  550 N Kingsbury St Unit 610, Chicago, IL 60654
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  /40

  $649,999

  $50K PRICE DROP Pending

  • 3 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  2657 W Thomas St Unit 2E, Chicago, IL 60622

  Spacious duplex up 3 bed, 3.1 bath penthouse filled with natural light in the bright and walkable Humboldt Park neighborhood. Enter your high ceiling living room with built-in bookshelves and a gas starter wood burning fireplace. The open-concept space transitions into the chef's kitchen with high-end appliances and ample storage space on the granite peninsula and pantry. Leading into the dining

  Sohaib Qadri Century 21 Universal

  2657 W Thomas St Unit 2E, Chicago, IL 60622
• 

  

  /23

  $650,000

  • 2 Beds
  • 2 Baths

  864 N Paulina St Unit 3, Chicago, IL 60622

  Penthouse Living with Unobstructed Chicago Skyline Views in Chicago's East Village! This 2 bed 2 bath top floor unit offers exceptional privacy, dramatic 13-foot ceilings, and unobstructed views of the iconic Chicago skyline. One of the home's standout features is the private rooftop deck with interior unit entry -an incredible space for entertaining, relaxing, or simply taking in the city from

  Erik Sachs @properties Christie's International Real Estate

  864 N Paulina St Unit 3, Chicago, IL 60622
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  /37

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,617 Sq Ft

  520 W Huron St Unit 704, Chicago, IL 60654

  There's something different about being on the top floor. The light is better, the city feels closer, and at the end of the day, you can step onto your own 450-square-foot private roof deck or One of a Kind three season room and watch Chicago light up around you. We know this is one of a kind because the developer of the building built this unit for himself. This 2-bedroom, 2-bath+three season

  Joel Holland Keller Williams ONEChicago

  520 W Huron St Unit 704, Chicago, IL 60654
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  /38

  $1,299,000

  • 3 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  1412 W Diversey Pkwy Unit B, Chicago, IL 60614

  Welcome to the penthouse at 1412 W. Diversey Parkway, an expansive two-level residence offering 3 bedrooms, 3 bathrooms, soaring ceilings, and exceptional indoor-outdoor living. Situated atop an intimate two-unit building, this spacious home is filled with natural light and presents an incredible opportunity to create a truly spectacular residence. Designed for both everyday living and

  Michelle Ward Compass

  1412 W Diversey Pkwy Unit B, Chicago, IL 60614

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