Penthouses for Sale in Chicago, IL

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  /36

  $725,000

  • 2 Beds
  • 2 Baths

  360 W Illinois St Unit 614, Chicago, IL 60654

  Rarely Available 2 Bed / 2 Bath Duplex Penthouse with Private Terrace Truly unique residence at the Sexton Lofts in premier River North. This two-level penthouse showcases soaring ceilings, exposed brick & timber, hardwood floors, and in-unit laundry. Main floor offers an open kitchen with quartz counters & stainless appliances, spacious dining/living area with fireplace, and balcony. Upstairs,

  Brittany Villalobos First In Realty, Inc.

  360 W Illinois St Unit 614, Chicago, IL 60654
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  /65

  $799,000

  • 2 Beds
  • 2 Baths
  • 1,850 Sq Ft

  1212 N Lake Shore Dr Unit 10CS, Chicago, IL 60610

  Experience true luxury living in this impeccably maintained and beautifully updated 2 bed, 2 bath residence on prestigious Lake Shore Drive. Enjoy spectacular lake views in this iconic Gold Coast location just steps from world-class shopping, dining, and Oak Street Beach. Spacious layout ideal for entertaining with a large living room and separate dining room. The modern kitchen features newer

  Jeremy Vitell Better Homes & Gardens Real Estate Connections

  1212 N Lake Shore Dr Unit 10CS, Chicago, IL 60610
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  /20

  $470,000

  • 2 Beds
  • 2 Baths

  230 W Division St Unit 1202, Chicago, IL 60610

  Located in the heart of Old Town, enjoy everything that this newly renovated 2 bed/2 bath condo has to offer! Large wrap around balcony with composite decking, split floor plan with open layout, 10 foot ceilings & southern exposure with tons of natural light & stunning skyline views. Upgraded kitchen features quartz counters, subway tile backsplash, new kitchen pendants, white cabinetry and

  Patrick Teets Jameson Sotheby's Intl Realty

  230 W Division St Unit 1202, Chicago, IL 60610
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  /27

  $2,899,900 New Construction

  • 7 Beds
  • 7 Baths

  1029 N Winchester Ave, Chicago, IL 60622

  Introducing a rare opportunity to own an exceptional, brand-new three-unit all-brick building in the heart of Wicker Park offering a total of 7 bedrooms + office, unmatched outdoor spaces, premium finishes, and an A+ location. Thoughtfully designed with cohesive high-end aesthetics throughout, each residence features custom Scandinavian-inspired cabinetry, quartz countertops, designer lighting,

  Melanie Giglio-Vakos Compass

  1029 N Winchester Ave, Chicago, IL 60622
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  /33

  $597,000

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

  446 E 48th St Unit 3E, Chicago, IL 60615

  Elevate your lifestyle in this top-floor Penthouse residence! Impeccably renovated 4BD/3BA home showcasing timeless character with today's modern finishes-quartz counters, shaker cabinetry, refinished hardwood floors, and designer lighting. Spacious living room with bay windows and fireplace, spa-inspired primary suite with clawfoot tub & rain shower, plus a private balcony and rear deck for

  Jaymi Block REMAX Legends

  446 E 48th St Unit 3E, Chicago, IL 60615
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  /23

  $244,500

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  4903 N Monticello Ave Unit 3, Chicago, IL 60625

  Welcome to this charming, 2 bedroom, 1 bathroom top floor penthouse suite located on a beautiful tree-lined street in Mayfair/Albany Park. Loads of natural sunlight,and featuring 3 outdoor spaces including a large private covered terrace and shared back deck plus shared backyard. There are hardwood floors throughout, and it's been recently painted. This home is the perfect oasis in the city. The

  Arlene Zingsheim Keller Williams ONEChicago

  4903 N Monticello Ave Unit 3, Chicago, IL 60625
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  /16

  $445,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  4730 S Champlain Ave Unit 3, Chicago, IL 60615

  This stunning 3-bedroom, 2-bathroom split-level penthouse is the epitome of modern luxury living. Featuring exquisite finishes and unparalleled attention to detail, this condo is designed for those who demand the best. From oversized windows that flood the space with natural light to designer lighting fixtures that add an elegant touch, every aspect of this home has been thoughtfully curated.

  Erika Finley Century 21 IMPACT

  4730 S Champlain Ave Unit 3, Chicago, IL 60615
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  /17

  $7,000,000

  • 40,000 Sq Ft

  7270 S South Shore Dr, Chicago, IL 60649

  Pleased to present the multifamily property at 7270 S. South Shore Dr. This asset represents a compelling investment opportunity in a vibrant community. The subject property is a 53-unit multifamily elevator building with a rooftop space located in the heart of Chicago's tree-lined South Shore neighborhood. It is conveniently situated fifteen minutes from the Loop and one block from the

  Tony Hardy Keller Williams ONEChicago

  7270 S South Shore Dr, Chicago, IL 60649
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  /28

  $199,999

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  745 S Independence Blvd Unit 3N, Chicago, IL 60624

  STUNNING Top-Floor residence positioned perfectly along one of the area's most scenic boulevards! This elegant home features a brand-new kitchen with high-end cabinetry, granite countertops, and an east-facing layout that welcomes glorious morning sunlight. The spacious kitchen flows into a dining or family room area, complete with patio doors leading to a large private deck with direct views of

  Jonie Montalbano @properties Christie?s International Real Estate

  745 S Independence Blvd Unit 3N, Chicago, IL 60624
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  /23

  $534,900

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  1524 S Sangamon St Unit 802, Chicago, IL 60608

  Experience breathtaking, unobstructed skyline views from every room in this stunning 2 bed, 2 bath penthouse in the heart of University Village. Thoughtfully designed with fully enclosed bedrooms and an expansive open-concept layout, this home offers an impressive living and entertaining space framed by floor-to-ceiling windows. The spacious primary suite features dual walk-in closets and a

  Kelly Ladewig Baird & Warner

  1524 S Sangamon St Unit 802, Chicago, IL 60608
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  /35

  $1,500,000 New Construction

  • 3 Beds
  • 3.5 Baths

  3036 N Sheffield Ave Unit 3, Chicago, IL 60657

  Welcome to East Lakeview's Newest Boutique Luxury development - 3036 N Sheffield. Comprised of 5 design-inspired homes, this property offers Open Floor Plans, Designer Finishes and Amazing Private Outdoor Space! This Full Floor 3 Bedroom / 3 1/2 Bathroom Penthouse spans the entire width of the building allowing for expansive room sizes, exceptional natural light and just over 2200 sqft of private

  James Sheehan Sheehan Real Estate

  3036 N Sheffield Ave Unit 3, Chicago, IL 60657
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  /14

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft

  2421 W Warren Blvd Unit 3, Chicago, IL 60612

  Immaculate 2BDR/2BTH 3rd floor Condo unit with stunning views of downtown Chicago from the private exclusive rooftop deck. Plenty of sunlight flooding the unit, 12 FT Ceilings, Hardwood floors throughout with carpet in bedrooms. Open concept living room, dining area, kitchen with ample cabinets, fireplace, SS Appliances, garbage disposal. Newer furnace/air conditioning unit and wash/dryer.

  Joann Brown Fulton Grace Realty

  2421 W Warren Blvd Unit 3, Chicago, IL 60612
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  /35

  $900,000

  • 3 Beds
  • 3.5 Baths

  600 N Kingsbury St Unit 1902, Chicago, IL 60654

  3 BR/3.5 bathroom penthouse duplex in the heart of River North. This unit is very generous in size and offers two levels of living space. Full living room, separate family room, private dining room and large kitchen all on the main floor. 2 full bedrooms and 2.5 bathrooms with gorgeous skyline views. Enter the upstairs level to a loft space with endless possibilities, a spacious primary bedroom

  Scott Newman Keller Williams ONEChicago

  600 N Kingsbury St Unit 1902, Chicago, IL 60654
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  /53

  $11,700,000

  • 5 Beds
  • 7 Baths
  • 8,500 Sq Ft

  800 N Michigan Ave Unit 64, Chicago, IL 60611

  An oasis above the clouds, this one-of-a-kind penthouse comprises the entire 64th floor at the prestigious Park Tower on North Michigan Avenue. Spanning 8,500 SQFT, this 15-room apartment was meticulously crafted by the renowned architectural firm Marvin Herman & Associates and Interior Designer, Mitchell Turnbough. With a 360-degree view of the city, this unique residence is designed to provide

  Carrie McCormick @properties Christie's International Real Estate

  800 N Michigan Ave Unit 64, Chicago, IL 60611
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  /13

  $979,000 New Construction

  • 3 Beds
  • 2.5 Baths

  2234 W Grand Ave Unit PH-401, Chicago, IL 60612

  Come experience the pinnacle of modern luxury in this masterfully designed 3-bedroom, 2.5 bath condo in West Town. The entire building is engineered for superior soundproofing with a sealed shell structure, 15-inch blown-in cellulose insulation between floors coupled with open-cell spray foam, Maxxon acoustic soundproofing rubber mattes, 1-inch of Maxxon Gypcrete concrete flooring, and the

  Roman Popovych Prodan Realty Inc

  2234 W Grand Ave Unit PH-401, Chicago, IL 60612
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  /41

  $1,350,000

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  2401 N Janssen Ave Unit 402, Chicago, IL 60614

  Massive highly upgraded combined penthouse unit in Lincoln Park in an intimate elevator building! Over 2700 square feet of living space on one level for super convenient single family home-like living. This northeast facing 4 bed 3 bath plus office also features a large main living and dining space with extra built-in bar with beer tap system and wine fridge perfect for entertaining parties of

  Joseph Semany Compass

  2401 N Janssen Ave Unit 402, Chicago, IL 60614
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  /39

  $1,225,000

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  1440 N Lake Shore Dr Unit 35A, Chicago, IL 60610

  This is the Penthouse your clients have been looking for! Magnificent custom residence on Lake Shore Drive! Perfect 4 en-suite bedroom - 4.1 bath layout with Spacious Primary Suite including sweeping unobstructed views, exercise/study, oversized walk-in dressing room, spa-like bath with heated floors, steam shower, soaking tub and separate W/C. Irresistibly priced with all the bells and whistles:

  Mark Markarian Jameson Sotheby's Intl Realty

  1440 N Lake Shore Dr Unit 35A, Chicago, IL 60610
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  /17

  $350,000

  • 2 Beds
  • 2 Baths

  1550 S Blue Island Ave Unit 1210, Chicago, IL 60608

  Pinnacle urban luxury defines this sleek high-rise penthouse. Step into a life of comfort and style at University Station! This split 2-bed, 2-bath corner unit commands breathtaking southeast city skyline views. Natural light floods the open-concept living area and gourmet kitchen. The piece de resistance is the unparalleled deck, offering an expansive outdoor oasis for morning coffee and

  Manuel Godinez RE/MAX Mi Casa

  1550 S Blue Island Ave Unit 1210, Chicago, IL 60608
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  /22

  $699,900

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

  1735 W Diversey Pkwy Unit 615, Chicago, IL 60614

  Amazing penthouse unit with 11' ceilings and an 85' long terrace! Open floor plan with hardwood floors throughout. Tremendous natural light with north facing windows that provide an unobstructed view. The living and dining room are highlighted by a decorative fireplace and dual sliding doors to the terrace. The kitchen is finished with quartz counters, under cabinet lighting and features an

  Ron Ehlers Compass

  1735 W Diversey Pkwy Unit 615, Chicago, IL 60614
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  /23

  $6,995,000

  • 4 Beds
  • 6 Baths
  • 7,147 Sq Ft

  451 E Grand Ave Unit PH66, Chicago, IL 60611

  One Bennett Park has taken its place among Chicago's most elite residences. Designed by Robert A.M. Stern Architects and developed by Related Midwest, this world class building was designed from the top down. Gracing the crown of this iconic lakefront tower, Penthouse 66 is a full-floor residence being offered as raw space. Turn a blank canvas into a one-of-a-kind residence designed specifically

  Brad Brondyke Jameson Sotheby's Intl Realty

  451 E Grand Ave Unit PH66, Chicago, IL 60611
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  /41

  $300,000 Pre-Foreclosure

  • 2 Beds
  • 2 Baths
  • 996 Sq Ft

  1001 W 15th St Unit 241, Chicago, IL 60608

  Fabulous 2-Bed/2-Bath Concrete Loft in Popular University Commons! Expect to be impressed by this sought-after split-bedroom floor plan featuring soaring 12' concrete ceilings, expansive north-facing floor-to-ceiling windows with beautiful treetop views, and generous living spaces. The wide living area includes hardwood floors, a cozy gas fireplace, space for a full-size dining table, and access

  Amanda McMillan @properties Christie's International Real Estate

  1001 W 15th St Unit 241, Chicago, IL 60608
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  /26

  $775,000

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

  Unlisted Address

  Stunning turnkey penthouse-one of only three on its floor-offering unmatched privacy, exceptional natural light, and sophisticated designer finishes. Originally built as a 3-bedroom, this home currently features an open third bedroom that enhances the living space but can easily be enclosed to restore the full 3-bed layout. Designed by Brininstool + Lynch Architects, this corner residence boasts

  Niles Patel CORE Capital Group LLC

  Unlisted Address
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  /28

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  2922 N Sheffield Ave Unit 3, Chicago, IL 60657

  This sophisticated 4-bedroom, 2.5-bath residence, ideally situated in the heart of Lakeview, combines striking contemporary design with luxurious modern comforts. Step inside to find rich espresso-stained hardwood floors and 8-foot solid-core doors throughout, complemented by sleek glass-paneled staircases that enhance the home's open, airy flow. Expansive windows on three sides flood the

  Nathan Binkley Compass

  2922 N Sheffield Ave Unit 3, Chicago, IL 60657
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  /29

  $899,000

  • 3 Beds
  • 2 Baths

  210 N Halsted St Unit 4, Chicago, IL 60661

  Penthouse living at its finest! Enjoy your own private rooftop oasis all summer long right in the heart of Fulton Market/West Loop! This spacious 3bed/2bath condo with an extra wide floor plan is an entertainers dream. Kitchen features espresso stained walnut cabinets, stainless steel appliances, quartz countertops and a large island. The east facing living room has stunning city views with large

  Melissa Mueller @properties Christie's International Real Estate

  210 N Halsted St Unit 4, Chicago, IL 60661
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  /27

  $115,000

  • 1 Bed
  • 1 Bath

  6700 S South Shore Dr Unit 21E, Chicago, IL 60649

  Experience Refined Lakeside Living Don't miss your chance to own this beautifully updated 1-bedroom, 1-bath condo offering serene views of the lake and city horizon through stunning floor-to-ceiling windows. The open-concept kitchen features sleek stainless steel appliances and an inviting eat-in area, flowing effortlessly into a spacious living room designed for both comfort and style. Enjoy

  Martisia Mitchell Real People Realty

  6700 S South Shore Dr Unit 21E, Chicago, IL 60649
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  /22

  $2,995,000

  • 3 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  132 E Delaware Place Unit 620507, Chicago, IL 60611

  NEW CONSTRUCTION PENTHOUSE floor residence with 11 ft ceilings in FOUR SEASONS/Bloomingdale's building. This residence has been gutted and architecturally redesigned in 2024. Sought after Northwest corner offers over 3500 sq. ft. with unobstructed panoramic views of Downtown, Lincoln Park and Lake Michigan. Live in total Luxury in this 3 bedroom 3.1 bath plus office/den/ ideal library. This full

  Sergio Aguirre Northlake Realtors

  132 E Delaware Place Unit 620507, Chicago, IL 60611
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  /40

  $649,900

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

  1535 W Estes Ave Unit 3, Chicago, IL 60626

  Introducing 1535 West Estes Avenue, located in the heart of East Rogers Park! Fully Renovated Condo Units! This 2025 beautiful, enormous, completely renovated to the studs 4 unit Condo development building features top-notch design and craftsmanship throughout. The property sits on a huge 30x180 foot lot located on a quiet street and showcases exquisite gorgeous limestone as well as new

  Peter Fotopoulos Baird & Warner

  1535 W Estes Ave Unit 3, Chicago, IL 60626
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  /9

  $1,200,000

  • 5 Beds
  • 7 Baths

  1422 N Maplewood Ave, Chicago, IL 60622

  Prime East Humboldt Park 3-unit building with 1 non-conforming 3BD/2BA garden unit. Built in the late-1990s with modern systems and well-maintained for 22+ years of ownership. Unit mix includes one 2BD/2BA layout and two 3BD/2BA layouts plus a non-conforming garden unit. The penthouse unit offers oversized bedrooms, vaulted ceilings with skylights, and a private rear balcony with exclusive entry.

  Adam Max Compass

  1422 N Maplewood Ave, Chicago, IL 60622
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  /52

  $2,000,000

  • 3 Beds
  • 3.5 Baths
  • 2,733 Sq Ft

  450 E Waterside Dr Unit 3302, Chicago, IL 60601

  This stunning penthouse combines dramatic 10'+ ceilings with panoramic Lake Michigan, River, and Navy Pier views-visible from every room. Designed for refined living, the expansive great room seamlessly connects living, dining, and a chef's kitchen, all enhanced by exquisite custom millwork and stone finishes that surpass developer standards. Three luxurious ensuite bedrooms provide exceptional

  Naomi Wilkinson Magellan Marketing Group LLC

  450 E Waterside Dr Unit 3302, Chicago, IL 60601
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  /11

  $199,000

  • 1 Bath
  • 660 Sq Ft

  780 S Federal St Unit 1202, Chicago, IL 60605

  Recently rehabbed top-floor penthouse studio in the historic Printers Square building. This bright 12th-floor unit features soaring ceilings, oversized north-facing windows, and dramatic skyline views. Spacious open layout with a defined foyer entry, wood laminate floors, and rare walk-in closet. Additional secured storage conveniently located on the same floor. Building amenities include fitness

  Kiki Parmar Kale Realty

  780 S Federal St Unit 1202, Chicago, IL 60605
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  /22

  $229,000

  • 1 Bed
  • 1 Bath
  • 755 Sq Ft

  535 N Michigan Ave Unit 1906, Chicago, IL 60611

  No rental cap restriction! Stunning south-facing 1 bedroom unit located on the Magnificent Mile. The building has been recently renovated with blend of comfort, contemporary full amenities, indoor swimming pool available year-round, 24-hour doorperson, and a beautifully-renovated penthouse community social room, as well as a 360-degree panoramic terrace with breathtaking views of the city. Close

  Kathy Li Century 21 S.G.R., Inc.

  535 N Michigan Ave Unit 1906, Chicago, IL 60611
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  /58

  $2,990,000 New Construction

  • 11 Beds
  • 8 Baths

  Chicago, IL 60614

  Exceptional New Booth Hansen-Designed Three-Unit Residence on an Extra-Long Lot Built by legendary architect Booth Hansen and developer Ogden Partners. This stunning investment and/or live in investment property sits on an extra-long 25' x 150' lot, allowing for expansive layouts and extraordinary natural light throughout every home. This thoughtfully designed masonry brick and limestone building

  Linda Levin Jameson Sotheby's Intl Realty

  Chicago, IL 60614
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  /28

  $559,900

  • 2 Beds
  • 2 Baths
  • 1,365 Sq Ft

  8 E Randolph St Unit 3301, Chicago, IL 60601

  Truly one-of-a-kind, this penthouse corner home showcases sweeping views of the lake, river, and iconic Chicago skyline from every room. Floor-to-ceiling windows flood the space with light and frame breathtaking vistas at every turn. The open layout is designed for both everyday comfort and entertaining, with a spacious living room that easily accommodates a dining area. The sleek, open kitchen

  D. Waveland Kendt @properties Christie's International Real Estate

  8 E Randolph St Unit 3301, Chicago, IL 60601
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  /18

  $459,900

  • 2 Beds
  • 2 Baths
  • 1,429 Sq Ft

  235 W Van Buren St Unit 4613, Chicago, IL 60607

  INCREDIBLE opportunity to own this oversized 2 bed PLUS DEN penthouse in the heart of the Loop! Enjoy 10 foot ceilings and dramatic floor to ceiling windows framing STUNNING skyline and partial lake views! Ideal layout features TONS of storage throughout including a massive storage room which can easily be converted to a home office, plus separate den, large open kitchen w/ breakfast bar that

  Lee Cherney Compass

  235 W Van Buren St Unit 4613, Chicago, IL 60607
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  /55

  $614,000

  • 2 Beds
  • 2 Baths
  • 2,000 Sq Ft

  3530 N Lake Shore Dr Unit 12B, Chicago, IL 60657

  Experience the charm of this Georgian-style residence meticulously designed by the acclaimed architectural firm of Rissman and Hirschfield. From the enchanting entrance to the panoramic lake views, this penthouse in East Lake View seamlessly integrated refined living with timeless allure. Step into the expansive foyer where classic elegance unfolds. This home draws inspiration from the

  Ledio Samarxhiu Real Broker LLC

  3530 N Lake Shore Dr Unit 12B, Chicago, IL 60657
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  /46

  $2,880,000

  • 3 Beds
  • 5 Baths
  • 5,382 Sq Ft

  Unlisted Address

  Exquisitely modern with unparalleled panoramic views of the Chicago skyline and Lake Michigan, Residence 60M1 at 161 E. Chicago Avenue is a masterfully reimagined 3-bedroom, 3.5-bath duplex penthouse within the exclusive Olympia Centre. A 2023 full-scale renovation, this 5,400-square-foot corner home represents the pinnacle of luxury design, craftsmanship, and technology. The main level unfolds

  Tim Salm Jameson Sotheby's Intl Realty

  Unlisted Address
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  /52

  $4,195,000

  • 3 Beds
  • 3.5 Baths
  • 3,695 Sq Ft

  211 N Harbor Dr Unit 4602, Chicago, IL 60601

  Step into luxury living with this one-of-a-kind penthouse residence, where modern design meets timeless elegance. Spanning two thoughtfully designed levels, this home offers open, light filled spaces, high-end finishes with stunning unobstructed views of Lake Michigan. With generous living areas, three ensuite bedrooms, two outdoor spaces, and countless amenities - from the kid's playroom and

  Daniel Pape HUDSON PARKER

  211 N Harbor Dr Unit 4602, Chicago, IL 60601
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  /37

  $1,995,000

  • 4 Beds
  • 3 Baths

  2773 N Hampden Ct Unit PH03, Chicago, IL 60614

  Top Floor Penthouse in East Lincoln Park - Featuring the Largest Private Rooftop in the Hampdens! Welcome to your smart-tech sanctuary in one of Chicago's most coveted neighborhoods-just steps from North Pond, the Zoo, Alcott Elementary, and the lakefront. This architectural showpiece blends sleek modern design with effortless indoor-outdoor living. Inside, discover a 3-bedroom + den, 3-bath

  Daniel Merrion Coldwell Banker Realty

  2773 N Hampden Ct Unit PH03, Chicago, IL 60614
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  /29

  $879,000

  • 2 Beds
  • 2 Baths
  • 2,250 Sq Ft

  16 N May St Unit 543, Chicago, IL 60607

  Rare offering: One level Penthouse condo in highly sought-after Block X gated community! This well maintained unit is flooded with natural light and offers the peace and quiet of a gated community all while being located in the heart of the West Loop! Enjoy indoor/outdoor living with access to the private, 350sf terrace which runs the full length of the unit and has the best view in the complex,

  Anne Loncar Coldwell Banker Realty

  16 N May St Unit 543, Chicago, IL 60607
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  /21

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  100 E 14th St Unit 2106, Chicago, IL 60605

  Enjoy full amenity living in this two bedroom plus den, two bathroom condo with prime South Loop location, stunning views, the epitome of move-in ready. Spacious living area filled with natural light from the floor to ceiling windows with Lake Michigan and cityscape views from every angle. Open concept layout offers a seamless flow from living to dining area with newly refinished hardwood floors

  Nadine Ferrata Compass

  100 E 14th St Unit 2106, Chicago, IL 60605

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