Luxury Homes for Sale in Chicago, IL

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  /61

  $18,500,000

  • 6 Beds
  • 7 Baths
  • 13,400 Sq Ft

  915 N Dearborn St, Chicago, IL 60610

  A rare piece of Chicago's history, the Thompson House at 915 N. Dearborn stands as one of the Gold Coast's original architectural treasures. Designed in 1888 by Cobb & Frost, the renowned architects behind the Newberry Library and University of Chicago, this grand residence was among the first to define the Gold Coast neighborhood after the Great Chicago Fire. For the next century, it was owned

  Millie Rosenbloom Baird & Warner

  915 N Dearborn St, Chicago, IL 60610
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  /8

  $18,000,000

  • Land
  • 3.28 Acres
  • $5,487,805 per Acre

  3278 N Milwaukee Ave, Chicago, IL 60618

  Incredible development opportunity. Belmont Triangle site in Avondale. Approx. 3.28 acres parcel at Belmont Ave, Milwaukee Avenue and Pulaski Road. | Strauss Realty, Ltd. is proud to offer a rare opportunity to redevelop a substantial, 3.28 acre contiguous site in the heart of Avondale-bordered by Pulaski Road (20K VPD), Belmont Avenue (16K VPD), and Milwaukee Avenue (17K VPD). This prominent

  Adam Schneiderman, SIOR Strauss Realty Ltd

  3278 N Milwaukee Ave, Chicago, IL 60618
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  /2

  $14,882,260

  • Land
  • 3.14 Acres
  • $4,739,573 per Acre

  5401-5447 N Wolcott Ave, Chicago, IL 60640

  GREAT OPPORTUNITY TO PURCHASE 148,826 SQ. FT. OF LAND ON THE CORNER OF WOLCOTT/BALMORAL! IDEAL OPPORTUNITY FOR RESIDENTIAL DEVELOPMENT. $100 PSF. LOT DIMENSIONS 254'x586'. LOCATED NEXT TO ROGERS PARK MONTESSORI SCHOOL. HALF A MILE FROM WINNEMAC PARK AND AMUNDSEN HIGH SCHOOL. BETWEEN TWO METRA STATIONS - PETERSON-RIDGE AND RAVENSWOOD ON UP-N LINE. 10 MINUTE DRIVE TO LAKE SHORE DRIVE.

  Craig Wolf Strauss Realty Ltd

  5401-5447 N Wolcott Ave, Chicago, IL 60640
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  $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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  /56

  $9,995,000

  • 10 Beds
  • 10 Baths
  • 13,400 Sq Ft

  2026 N Kenmore Ave, Chicago, IL 60614

  Unique opportunity for the luxury homeowner who wants to provide an opportunity for an extended family habitat, live in nanny, or even business associates to be close in the huge coach house over the attached 5 car garage. The coach house also could be a huge basketball court with not much effort. This outstanding renovation was customized to perfection by Soucie Horner for this current owner who

  Emily Sachs Wong @properties Christie's International Real Estate

  2026 N Kenmore Ave, Chicago, IL 60614
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  /46

  $8,900,000

  • 4 Beds
  • 4.5 Baths
  • 7,880 Sq Ft

  159 E Walton Place Unit PH, Chicago, IL 60611

  Own the pinnacle of Chicago elegance in this 7880 sq ft duplex penthouse, formerly home to Vince Vaughn and the original headquarters of Hugh Hefner's Playboy enterprise. The Palmolive Building is a true Art Deco icon- its historic beacon once lit the skies to guide pilots to Midway Airport and today it shines as one of the most distinguished addresses in the city. This two-story residence is the

  Brian Loomis Jameson Sotheby's Intl Realty

  159 E Walton Place Unit PH, Chicago, IL 60611
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  /9

  $8,500,000

  • Land
  • 0.33 Acre
  • $25,757,576 per Acre

  2135 W Armitage Ave, Chicago, IL 60647

  A rare and exceptional opportunity to redevelop a prime site in the heart of Bucktown-truly a once-in-a-generation offering. Less than 2 blocks from the intersection of Armitage and Damen, this prominent site includes six buildings and multiple parking lots across 2135-2147 W. Armitage Ave. With 144 feet of frontage on Armitage and a total land area of 14,400 square feet (144x101), the site

  Peter Fotopoulos Baird & Warner

  2135 W Armitage Ave, Chicago, IL 60647
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  /90

  $8,360,000

  4358 S Prairie Ave, Chicago, IL 60653

  7.5 CAP Welcome to TPAL, The Prairie Ave Lofts, a Crown Jewel of the Bronzeville Collection spans 125 x 160.58 just under a 1/2 acre perfectly positioned on a prime corner in well located high growth Bronzeville 1/4 block to Green Line and Pendleton Park. An Iconic Classic Chicago All Masonry 31-unit prominent walk up with distinctive 5 entrances, steel rear decks, private all masonry

  Karen Biazar North Clybourn Group, Inc.

  4358 S Prairie Ave, Chicago, IL 60653
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  /36

  $8,000,000

  • Land
  • 0 Acre

  165 N May St, Chicago, IL 60607

  Rare Opportunity to acquire sought after Fulton Market / West Loop Redevelopment Site. 107x134 foot lot 14,300 square feet. C1-2 Zoning. Lot contains 30,000 square foot brick construction building with side parking lot. Building structure is a shell building ready for new ideas. Electric and Plumbing to site. Build new construction or renovate existing building. Great for ground level restaurant

  Peter Fotopoulos Baird & Warner

  165 N May St, Chicago, IL 60607
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  /73

  $7,999,000 New Construction

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

  363 E Wacker Dr Unit 9101, Chicago, IL 60601

  Perched atop the iconic St. Regis Chicago, this full-floor penthouse is the highest residential customizable home in the city and the Midwest! Spanning the entire 91st floor, this raw space offers a rare chance to create a one-of-a-kind residence tailored entirely to your vision. The ONLY unit in the building that can be fully customized, this offers 360-degree views of Chicago's world-renowned

  Laura England Compass

  363 E Wacker Dr Unit 9101, Chicago, IL 60601
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  /80

  $7,995,000

  • 6 Beds
  • 8 Baths
  • 9,512 Sq Ft

  1878 N Orchard St, Chicago, IL 60614

  Stunning beyond words, this East Lincoln Park masterpiece redefines luxury at every turn. Set on a 36x131 on coveted Orchard street, this 9,500 square foot home speaks to a most discerning buyer seeking the ultimate blend of superior craftsmanship and refined luxury. A chic city retreat featuring a plunge pool and beautifully landscaped yard. Upon entering, you are welcomed by the striking drama

  Susan Miner Premier Relocation, Inc.

  1878 N Orchard St, Chicago, IL 60614
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  /50

  $7,995,000

  • 4 Beds
  • 4.5 Baths
  • 6,085 Sq Ft

  14 W Superior St Unit 6900, Chicago, IL 60654

  Astonishing FULL FLOOR home with breathtaking 360 degree views, outdoor space, direct elevator access and bespoke finishes! Still time to customize your home to the caliber you have come to expect from JDL Development!! Completion slated for second quarter 2026! Welcome to One Chicago - 77 visionary homes in the sky, starting on the 44th floor, with spectacular city and lake views. Merging the

  Nancy Tassone Jameson Sotheby's Intl Realty

  14 W Superior St Unit 6900, Chicago, IL 60654
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  $7,250,000

  • 5 Beds
  • 5.5 Baths
  • 7,462 Sq Ft

  189 E Lake Shore Dr Unit 18, Chicago, IL 60611

  Amazing, dramatic penthouse in a classic vintage building on East Lake Shore Drive! This home has been completely renovated with over 7400 square feet of luxurious finishes and offers expansive lake & city views plus 2 terraces with 550 square feet of private outdoor space. Walk off the elevator into this full floor home featuring oversized windows and extraordinary ceiling height make this home

  Emily Sachs Wong @properties Christie's International Real Estate

  189 E Lake Shore Dr Unit 18, Chicago, IL 60611
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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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  /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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  $6,950,000

  • 5 Beds
  • 6 Baths
  • 8,400 Sq Ft

  800 N Michigan Ave Unit 63, Chicago, IL 60611

  Remarkable opportunity to acquire full floor Park Tower penthouse at a truly outstanding value. Delivering panoramic 360 degree views of Chicago's world-class architecture and Lake Michigan, plus captivating sunrise to sunset views. This 5 bedroom 4.2 bath home spans 8,400 square feet perched atop the Park Hyatt Hotel, where first-class amenities are at your disposal: Spa, Indoor Pool, Fitness,

  Jeffrey Lowe Compass

  800 N Michigan Ave Unit 63, Chicago, IL 60611
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  /2

  $6,950,000

  • 6 Beds
  • 7 Baths
  • 6,000 Sq Ft

  1865 N Burling St, Chicago, IL 60614

  Truly the last new construction opportunity on the most coveted block in Lincoln Park! The Savane Properties Design Build team presents an exceptional custom new construction home on the most desirable street in Chicago on a rare extra wide lot. This home offers 5 to 8 Bedrooms, 5 plus baths, state-of-the-art luxury finishes, expansive indoor/outdoor living spaces, lavish master suite, Front

  Tom Moran @properties Christie's International Real Estate

  1865 N Burling St, Chicago, IL 60614
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  /50

  $6,900,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 4,798 Sq Ft

  451 E Grand Ave Unit 6111, Chicago, IL 60611

  Welcome to Unit 6111, a meticulously designed residence perched high above Chicago's lakefront in the coveted One Bennett Park, designed by Robert A.M. Stern Architects. This home showcases stunning views and custom craftsmanship, representing the pinnacle of modern luxury living. With 11' ceilings throughout the impressive 4,800 Sf interior, this 3bed + office home in the sky offers an

  Brant Booker Jameson Sotheby's Intl Realty

  451 E Grand Ave Unit 6111, Chicago, IL 60611
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  /10

  $6,500,000

  • 5 Beds
  • 8 Baths

  1438 N Dearborn St, Chicago, IL 60610

  Behind this classic historic Gold Coast facade lies an extraordinary reinvention. Meticulously stripped to the shell and rebuilt just two years ago as a custom residence for the current owners by Environs Development, this is a rare Gold Coast resale that lives like new construction - thoughtfully reimagined with a floorplan that caters perfectly to modern living without a single compromise. In a

  Kevin Wood @properties Christie's International Real Estate

  1438 N Dearborn St, Chicago, IL 60610
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  /48

  $6,450,000

  • 4 Beds
  • 5.5 Baths
  • 4,708 Sq Ft

  363 E Wacker Dr Unit 6106, Chicago, IL 60601

  6106 is a premier residence at the 5 Star St. Regis Chicago with jaw dropping views and quite possibly the best amenities in town. In the architectural landmark by Jeanne Gang, this 4708 SF 4 bed/5.1 bath home has an 80' wide great room with unobstructed N / E / S panoramic views of Lake Michigan, Chicago River, Grant Park, and the city skyline. Ideal for entertaining, this open-concept space

  Ryan Preuett Jameson Sotheby's Intl Realty

  363 E Wacker Dr Unit 6106, Chicago, IL 60601
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  /8

  $6,290,000

  • 65,000 Sq Ft

  5200 S Woodlawn Ave, Chicago, IL 60615

  This building is located in Hyde Park, one of the top rated Chicago communities. It also is one of the most culturally diverse neighborhoods in the City. It is adjacent to the major shopping area in Hyde Park and a short walking distance to the University of Chicago Campus. The mix of units include three 3-bedroom 2 full bathroom apartments, twelve 2-bedroom 2 full bathroom apartments and seven

  Donna Schwan MetroPro Realty LLC

  5200 S Woodlawn Ave, Chicago, IL 60615
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  /2

  $6,255,000

  • Land
  • 0 Acre

  1728 N Clybourn Ave, Chicago, IL 60614

  Dennis Claussen The Richden Co.

  1728 N Clybourn Ave, Chicago, IL 60614
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  /2

  $6,178,474

  • 4 Beds
  • 10 Baths
  • 4,568 Sq Ft

  363 E Wacker Dr Unit 5806, Chicago, IL 60601

  Gorgeous wrap around North, East and South views of Lake , River, City and Shoreline. East facing 32 x 9 foot terrace. Gracious home with four ensuite bedrooms. Master Bedroom with his and hers baths and large closets. Beautiful finishes brought together by World-renowned interior design specialists Hirsch Bedner Associates (HBA) Gaggenau & Thermador appliances, Snaidero cabinetry with cantilever

  Leila Zammatta Magellan Marketing Group LLC

  363 E Wacker Dr Unit 5806, Chicago, IL 60601
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  /54

  $6,000,000

  • 4 Beds
  • 5.5 Baths
  • 4,029 Sq Ft

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

  Spectacular Penthouse unit on the 86th floor, designed by the world-renowned architect Adrian Smith. This super upscale residence is turn-key and fully furnished, ready for immediate move-in. With 4 bedrooms + Den and 5.1 baths, each room is glamorously and professionally designed, offering unobstructed N, E, S, W & lake views. Revel in super high ceilings, panoramic floor-to-ceiling windows, and

  Chezi Rafaeli Coldwell Banker Realty

  401 N Wabash Ave Unit 86A, Chicago, IL 60611
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  /38

  $5,995,000

  • 3 Beds
  • 3.5 Baths
  • 5,500 Sq Ft

  159 E Walton Place Unit 31A, Chicago, IL 60611

  Full floor Art Deco masterpiece pays homage to the 1929 built Palmolive Building with no details overlooked. This full floor renovation by Liederbach & Graham Architects, designed by Steven Gambrel includes private elevator foyer, (3) bedrooms, sitting room plus library with adjacent office. Caretti Terrazzo floor in main foyer. French Oak-Parquet de Versailles flooring throughout main living

  

  Ken Jungwirth

  @properties Christie's International Real Estate

  (773) 537-4571

  159 E Walton Place Unit 31A, Chicago, IL 60611
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  /69

  $5,995,000

  • 6 Beds
  • 11 Baths
  • 9,000 Sq Ft

  950 N Michigan Ave Unit 4605, Chicago, IL 60611

  Perched near the top of one of Chicago's most iconic addresses, Unit 4605 at One Magnificent Mile is a rare, architecturally significant duplex offering nearly 9,000 square feet of masterfully curated living space. Designed by Wheeler Kearns Architects with interiors by Set Setting Studio, this 6 bedroom, 8 full and 3 half bathroom residence combines warm contemporary design with sweeping views

  Ryan Preuett Jameson Sotheby's Intl Realty

  950 N Michigan Ave Unit 4605, Chicago, IL 60611
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  $5,750,000

  • 6 Beds
  • 8 Baths
  • 9,740 Sq Ft

  1019 N Wolcott Ave, Chicago, IL 60622

  Prepare to be captivated by one of Chicago's most extraordinary real estate offerings: The Lincoln Street Bath House, a jaw-dropping fusion of historic grandeur and cutting-edge luxury. This rare architectural 10,000 square foot masterpiece has been transformed into a spectacular private residence that radiates style, sophistication, and one-of-a-kind character. Inspired by the opulence of

  Jennifer Mills Jameson Sotheby's Intl Realty

  1019 N Wolcott Ave, Chicago, IL 60622
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  /48

  $5,500,000

  Unlisted Address

  Brand new brick buildings near transportation! 6-unit and 9-unit buildings sitting side by side. 20 parking spaces, every unit comes with a storage space. The units feature hardwood floors, designer kitchens with quartz counters and stainless appliances. 12 out of 15 units are tenant-occupied.

  Marika Kakhiani Pedestal Realty LLC

  Unlisted Address
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  /4

  $5,500,000

  • Land
  • 0 Acre

  1113 W Randolph St, Chicago, IL 60607

  Prime Time Location. Don't miss the rare opportunity to own on Randolph Street in the West Loop/Fulton Market neighborhood! This three-story building on Randolph St Restaurant Row is situated on a 5000 square foot lot, and it awaits your next restaurant or upscale boutique retail space. At approximately 11,375 square feet, the high-rise mixed-use zoning allows for retail and office space along

  Peter Fotopoulos Baird & Warner

  1113 W Randolph St, Chicago, IL 60607
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  /24

  $5,375,000

  • 2 Beds
  • 10 Baths
  • 21,170 Sq Ft

  452 N Morgan St, Chicago, IL 60642

  Rare opportunity to own 100% fee-simple interest in a premier mixed-use building at the intersection of Fulton Market and River West. The property offers approximately 19,238 SF, including 8,991 SF of residential loft space across three levels with a private garage, elevator access, and a penthouse rooftop. The ground floor and part of the 2nd floor are leased to FCB Chicago, a global

  Karen Schwartz Baird & Warner

  452 N Morgan St, Chicago, IL 60642
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  /8

  $5,250,000

  • 7 Beds
  • 9 Baths
  • 6,700 Sq Ft

  3523 N Bosworth Ave, Chicago, IL 60657

  Located on the most sought-after block in Southport corridor and ideally situated on an extra-wide 37.5 foot lot, this architecturally significant, design inspired home has been thoroughly planned to provide a thoughtful layout and awe-inspiring features to enhance day-to-day life. With just over 6700ft of living space, the expansive floor plan provides 7 bedrooms, 7 full baths and 2 half baths.

  Andrew Thurston Sheehan Real Estate

  3523 N Bosworth Ave, Chicago, IL 60657
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  /52

  $5,200,000

  • 7 Beds
  • 5.5 Baths
  • 8,400 Sq Ft

  1515 N North Park Ave, Chicago, IL 60610

  Nestled on the prestigious North Park Avenue, Significant Mansion stands as a remarkable architectural gem in the vibrant Old Town/Gold Coast neighborhood. This custom-built residence, constructed from exquisite masonry brick and limestone, spans an impressive 8,000 square feet and occupies a generous double lot measuring 50 feet in width. The property boasts an expansive side yard and

  Chaz Walters Coldwell Banker Realty

  1515 N North Park Ave, Chicago, IL 60610
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  /93

  $4,995,000

  • 5 Beds
  • 7 Baths
  • 8,250 Sq Ft

  1407 N Hoyne Ave, Chicago, IL 60622

  A sophisticated presence, landmark status, architectural integrity, and an unprecedented outdoor footprint for Wicker Park, 1407 N. Hoyne Ave. is a one-of-a-kind opportunity for the homeowner who wants an expansive city estate with pedigree and a modern program. Originally built for beer baron John H. Rapp in 1886, this 8250 SqFt-square-foot, 5+ bed/5.5 bath single-family home underwent a

  Tim Salm Jameson Sotheby's Intl Realty

  1407 N Hoyne Ave, Chicago, IL 60622
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  /37

  $4,995,000

  • 6 Beds
  • 9 Baths
  • 8,500 Sq Ft

  1550 N State Pkwy Unit LIB-ABC, Chicago, IL 60610

  Experience the pinnacle of luxury living in this stately 8,500+ Sq.Ft. residence at the prestigious Benjamin Marshall's Beaux Arts building. Situated in the desirable Gold Coast neighborhood and boasting breathtaking views of the South end of Lincoln Park, this magnificent one-of-a-kind home has been seamlessly combined exuding elegance and functionality. Enjoy a spacious open floorplan designed

  Natasha Motev Jameson Sotheby's Intl Realty

  1550 N State Pkwy Unit LIB-ABC, Chicago, IL 60610
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  /10

  $4,900,000

  • 4 Beds
  • 4.5 Baths
  • 5,215 Sq Ft

  1447 N Dearborn St Unit 1N, Chicago, IL 60610

  Eight new construction, exclusive, full-floor residences offer a refined lifestyle that blends eclectic interiors with unparalleled luxury and an estimated delivery date of 12 months. Discover an extraordinary opportunity to live boldly at 1447 N. Dearborn, an enduring Gold Coast icon. Nestled on a quiet street, these residences overlook treelined and courtyard views, offering a sense of peace in

  Carrie McCormick @properties Christie's International Real Estate

  1447 N Dearborn St Unit 1N, Chicago, IL 60610
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  $4,700,000 Pre-Foreclosure

  5011 S Drexel Blvd, Chicago, IL 60615

  Exclusively engaged to market for sale Drexel House [5017 S DrexelBlvd], an 8-unit, 38-bedroom multifamily property in Chicago's Hyde Park neighborhood.5017 S Drexel is a gut-rehabbed property showcasing a rare and highly functional unit configuration: [7] spacious five-bedroom apartments and [1] three-bedroom unit, all equipped with three bathrooms. Each residence has been meticulously updated,

  Ryan Blake Nara Advisors, Inc

  5011 S Drexel Blvd, Chicago, IL 60615
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  /68

  $4,475,000

  • 5 Beds
  • 7 Baths
  • 6,815 Sq Ft

  1434 N Dearborn St, Chicago, IL 60610

  On one of the Gold Coast's most enchanting tree-lined streets, this limestone residence blends historic grace with modern sophistication. Set on an extraordinary 25x149 lot, the home offers soaring ceilings, original millwork, and elegant architectural detail seamlessly paired with subtle, natural Scandinavian design, and amazing outdoor space. Flooded with natural light throughout, every space

  Carrie McCormick @properties Christie's International Real Estate

  1434 N Dearborn St, Chicago, IL 60610
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  /29

  $4,400,000

  • 6 Beds
  • 6.5 Baths
  • 5,200 Sq Ft

  2119 N Seminary Ave, Chicago, IL 60614

  Just is time for the Holidays! We are incredibly excited to offer this amazing opportunity to build your Custom Dream Home on the most sought after block in Lincoln Park. Ideally situated on tree lined Seminary and nestled in the top rated Oscar Mayer and Lincoln school Districts, this home will impress the most discerning of buyers. Comprised of 6 Bedrooms and 6.1 bathrooms, this home showcases

  Andrew Thurston Sheehan Real Estate

  2119 N Seminary Ave, Chicago, IL 60614
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  /40

  $4,395,000

  • 7 Beds
  • 7.5 Baths
  • 7,607 Sq Ft

  1425 N State Pkwy, Chicago, IL 60610

  Grand and elegant home in the heart of the Gold Coast on a wide and deep lot. Extraordinary --approximately 8000 square foot --floorplan. Beautifully updated and maintained. The house has huge gracious formal entertaining rooms and wonderful casual/comfortable rooms for day-to-day living. The main level has a lovely entry foyer and grand formal living room with an adjacent dining room. The

  Suzanne Gignilliat @properties Christie's International Real Estate

  1425 N State Pkwy, Chicago, IL 60610
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  /57

  $4,300,000

  • 4 Beds
  • 3.5 Baths
  • 5,250 Sq Ft

  800 N Michigan Ave Unit 3501, Chicago, IL 60611

  This extraordinary, elegant residence at Park Tower stands as a testament to sophistication and grandeur. Custom designed by Robert Klingel, elegance surrounds you in this expansive 5,250 square foot, 4 bedroom plus paneled library / office. This home has been meticulously crafted using only the finest materials and design. A grand foyer welcomes you into the home, setting the tone for the

  Carrie McCormick @properties Christie's International Real Estate

  800 N Michigan Ave Unit 3501, Chicago, IL 60611

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