Luxury Homes for Sale in Chicago, IL

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  /54

  $21,000,000

  • 6 Beds
  • 5.5 Baths
  • 25,000 Sq Ft

  1355 N Astor St, Chicago, IL 60610

  Presenting an unparalleled opportunity to acquire one of Chicago's most distinguished estates - an historic residence offering over 25,000 square feet of total living space, set on nearly one-third of an acre along the Gold Coast's prestigious Astor Street. This is an exceptionally wide and long lot like no other. Originally designed by acclaimed architect Howard Van Doren Shaw for the Goodman

  Emily Sachs Wong @properties Christie's International Real Estate

  1355 N Astor St, Chicago, IL 60610
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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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  $12,250,000

  • 6 Beds
  • 6.5 Baths
  • 8,690 Sq Ft

  800 N Michigan Ave Unit 67, Chicago, IL 60611

  The last raw penthouse available in the Gold Coast! An amazing opportunity to transform this true duplex Penthouse at Chicago's esteemed Park Hyatt. Offering the absolute best combination of 360-degree Lake Michigan and City skyline views, 12-foot ceilings, 5-Star Hotel amenities, 700sf of private outdoor space atop the duplex, NoMi Club, and access to the best shopping and dining the Gold Coast

  Susan Miner Premier Relocation, Inc.

  800 N Michigan Ave Unit 67, Chicago, IL 60611
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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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  /4

  $9,750,000

  • Land
  • 23,522 Sq Ft
  • $18,055,556 per Acre

  1375 W Lake St, Chicago, IL 60607

  Pleased to offer for sale a 23,000 SF re-development opportunity in Chicago's dynamic Fulton Market neighborhood. The property, located at 1375 W Lake Street, has been the longtime home of "Bottom Lounge", a renowned 18,000 SF hospitality venue specializing in live music with a full-service restaurant kitchen, large bar/restaurant space and a 2nd floor catering facility with a large outdoor deck

  Wayne Caplan Sperry Van Ness

  1375 W Lake St, Chicago, IL 60607
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  /87

  $8,995,000

  • 7 Beds
  • 5.5 Baths
  • 8,691 Sq Ft

  1853 N Burling St, Chicago, IL 60614

  Set on an expansive 44-ft-wide lot on the most coveted block of one of Chicago's most prestigious streets, 1853 N Burling is an exceptional custom-built estate. Situated in the heart of Lincoln Park, this architectural tour de force seamlessly combines masterful craftsmanship & refined modern living. Designed for extraordinary living, every element of this home has been carefully curated to

  Carrie McCormick @properties Christie's International Real Estate

  1853 N Burling St, Chicago, IL 60614
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  /21

  $8,495,000

  4742 S Michigan Ave, Chicago, IL 60615

  Unbelievable trophy-piece opportunity, three 8 unit boutique buildings, 24 Units fully stabilized, condo-quality and developed in 2025 in the Heart of Bronzeville. Each building features TWO front and back 3 bed 3 bath duplex units and SIX front and back 2 bed/2 bath simplex units. Many high-design details, from hallway accents to primary suite wall details meant to set this apart. Highlights

  Karen Biazar North Clybourn Group, Inc.

  4742 S Michigan Ave, Chicago, IL 60615
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  /56

  $8,450,000

  • 6 Beds
  • 9 Baths
  • 9,100 Sq Ft

  3026 N Lake Shore Dr, Chicago, IL 60657

  Rare opportunity to own an impeccably maintained single-family residence on Lake Shore Drive, situated on an expansive 66' x 200' lot with approximately 9,000 square feet under roof. This exceptional home offers 7 bedrooms and 7.5 baths and features multiple outdoor living spaces, including a Sport Court, a 30' x 25' terrace, and a 30' x 20' garage rooftop terrace with a custom outdoor

  Brant Booker Jameson Sotheby's Intl Realty

  3026 N Lake Shore Dr, Chicago, IL 60657
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  /16

  $8,415,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 5,497 Sq Ft

  363 E Wacker Dr Unit 7301, Chicago, IL 60601

  Introducing the Sky 360 Residences of St Regis Residences Chicago's New Luxury residence, an architectural masterpiece, designed by Jeanne Gang located in Lakeshore East. World-renowned interior design specialists Hirsch Bedner Associates (HBA) designed every interior, condo detail, & common space with no element overlooked. 11'4" ceiling heights with recessed lighting package, motorized window

  Leila Zammatta Magellan Marketing Group LLC

  363 E Wacker Dr Unit 7301, Chicago, IL 60601
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  /46

  $8,400,000

  • 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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  /50

  $8,350,000

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

  14 W Superior St Unit 7100, Chicago, IL 60654

  Astonishing FULL FLOOR home with breathtaking 360 degree views, outdoor space, direct elevator access and bespoke finishes! Delivery in August. Welcome to One Chicago - 77 visionary homes in the sky, starting on the 44th floor, with spectacular city and lake views. Merging the exclusive neighborhoods of the Gold Coast and River North, One Chicago offers a whole new perspective on city living,

  Nancy Tassone Jameson Sotheby's Intl Realty

  14 W Superior St Unit 7100, Chicago, IL 60654
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  $7,999,999

  • Land
  • 14,374 Sq Ft
  • $24,242,421 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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  /45

  $7,750,000

  • 5 Beds
  • 4.5 Baths
  • 6,031 Sq Ft

  1838 N Burling St, Chicago, IL 60614

  Classic limestone and brick single-family home on two and a half lots on coveted Burling Street with spectacular outdoor space. This outdoor footprint includes a swimming pool, outdoor kitchen, temperature controlled four-season glass atrium with accordion windows, sport court, and a gated parking pad for guests. The main level features high ceilings across a large living room with hardwood

  Ryan Preuett Jameson Sotheby's Intl Realty

  1838 N Burling St, Chicago, IL 60614
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  $7,500,000

  • 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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  /36

  $7,500,000

  • Land
  • 0 Sq Ft

  165 N May St, Chicago, IL 60607

  Looking at all Offers - 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

  Peter Fotopoulos Baird & Warner

  165 N May St, Chicago, IL 60607
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  $7,500,000

  • 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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  /41

  $7,000,000

  • 3 Beds
  • 3.5 Baths

  435 N Michigan Ave Unit 2203, Chicago, IL 60611

  A rare turnkey 3 bedroom + den residence with one of the most architecturally significant private outdoor spaces in Chicago. The terrace is framed by original Gothic limestone with panoramic views of Lake Michigan, the Chicago River, and city skyline in the iconic Tribune Tower. 2203 seamlessly blends architectural pedigree with cutting-edge elegant design. A gracious foyer leads to the

  Ryan Preuett Jameson Sotheby's Intl Realty

  435 N Michigan Ave Unit 2203, Chicago, IL 60611
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  $6,995,000

  3920 S Calumet Ave, Chicago, IL 60653

  Fully Stabilized Bronzeville Location-Series of 7 New/er Construction 3 Flat all 3 bedroom 2 bath units rear patio/decks all with 3 car garages- 21 total units. Intelligently designed apartments featuring clean white cabinetry in a professional kitchen setting, stainless steel appliance package, quartz island with a full backsplash and dedicated dining areas in each. Rich and warm wide planked

  Karen Biazar North Clybourn Group, Inc.

  3920 S Calumet Ave, Chicago, IL 60653
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  /2

  $6,950,000 New Construction

  • 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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  /46

  $6,500,000

  Unlisted Address

  David McLennan Pearson Realty Group

  Unlisted Address
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  /53

  $6,500,000 New Construction

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

  Chicago, IL 60611

  Perched 61 stories above Chicago's lakefront, Residence 6111 at One Bennett Park delivers architectural distinction by Robert A.M. Stern with exquisite custom interiors and commanding citytolake panoramas. A private foyer introduces 4,800 square feet of living space with 11foot ceilings, handpainted Venetian plaster, and herringbone oak floors under a sculpted glass fixture by John Pomp. The

  Brant Booker Jameson Sotheby's Intl Realty

  Chicago, IL 60611
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  /70

  $6,451,902 New Construction

  • 4 Beds
  • 5.5 Baths
  • 4,779 Sq Ft

  363 E Wacker Dr Unit 5506, Chicago, IL 60601

  Chicago's New Luxury Tower an architectural masterpiece, designed by Jeanne Gang complimented by a St Regis 5 Star Hotel located in Lakeshore East. World-renowned interior design specialists Hirsch Bedner Associates (HBA) created four distinct finish palettes with no detail overlooked. Gaggenau& Thermador appliances, Snaidero cabinetry with cantilever countertops, wide plank hardwood flooring

  Leila Zammatta Magellan Marketing Group LLC

  363 E Wacker Dr Unit 5506, 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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  /72

  $6,000,000

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

  1454 N Dearborn St, Chicago, IL 60610

  Nestled in the heart of Chicago's prestigious Gold Coast, this extraordinary residence commands attention from its rare 30 X 150 corner parcel- a true trophy property on one of the neighborhood's most coveted blocks. Listed on The National Register of Historic Places a masterful two year renovation provides a seamless blend of timeless elegance and modern refinement, showcasing impeccable

  Kathleen Malone Compass

  1454 N Dearborn St, Chicago, IL 60610
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  /26

  $6,000,000

  1508 W Farwell Ave, Chicago, IL 60626

  COURT YARD BUILDING! 22-Unit Apartment Building with 22 Parking Spaces - Prime Rogers Park Location. Exceptional investment opportunity in the heart of Rogers Park! This solid brick 22-unit multi-family building includes a rare 22 adjacent parking spaces, all included in the sale. The property has been remodeled with updated kitchens and bathrooms, offering strong rental appeal and low

  

  Michael Stangel

  @properties Christie's International Real Estate

  (312) 764-1452

  1508 W Farwell Ave, Chicago, IL 60626
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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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  /65

  $5,995,000

  • 3 Beds
  • 6 Baths
  • 6,500 Sq Ft

  1524 N Astor St, Chicago, IL 60610

  A rare architectural offering on one of Chicago's most coveted residential streets, this is the northernmost home on Astor, distinguished by its commanding position and oversized windows overlooking the Cardinal's Mansion and Lincoln Park. The setting provides exceptional privacy and natural light, a rarity in the city. Originally designed as a mid century modern residence by noted Chicago

  Jennifer Ames Engel & Voelkers Chicago

  1524 N Astor St, Chicago, IL 60610
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  /64

  $5,950,000

  • 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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  $5,900,000

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

  800 N Michigan Ave Unit 63, Chicago, IL 60611

  Unparalleled opportunity to own a full floor Park Tower penthouse at a truly outstanding value. Spanning 8,400 square feet, this residence offers 360-degree views of Chicago's iconic skyline, world-class architecture, and Lake Michigan, delivering front-row sunrise to sunset views. Perched above the Park Hyatt Hotel, this 5-bedroom, 4.2-bath home provides access to top-tier amenities: Spa, Indoor

  Jeffrey Lowe Compass

  800 N Michigan Ave Unit 63, Chicago, IL 60611
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  /62

  $5,795,000

  • 6 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  1755 N Mohawk St, Chicago, IL 60614

  Magnificent custom-built limestone masonry single-family home, with over 6,500 Sq. Ft. of pure luxury. Situated on a coveted East Lincoln Park double lot, the home offers an unparalleled blend of privacy, luxury, and outdoor living rarely found in the city. Still in the hands of its original owners, this remarkable residence was thoughtfully designed for both family living and grand entertaining.

  Natasha Motev Jameson Sotheby's Intl Realty

  1755 N Mohawk St, Chicago, IL 60614
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  /24

  $5,250,000 New Construction

  • 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 Meridian Real Estate Chicago LLC

  3523 N Bosworth Ave, Chicago, IL 60657
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  /2

  $5,250,000 New Construction

  • 8 Beds
  • 7.5 Baths
  • 7,118 Sq Ft

  Chicago, IL 60657

  Amazing design/build opportunity in the Southport Corridor coming soon from Environs on a 37.5' lot and a half with a breezeway attachment to an attached 3 car garage with Mudroom! This 7,100 square foot, 8 BR, 7.5 BA home will feature a highly functional, unusually open layout and offers 4 BR suites on the 2nd level including an expansive Primary Suite. The third floor features a spacious 3rd

  Kevin Wood @properties Christie's International Real Estate

  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 entrance,

  Chaz Walters Coldwell Banker Realty

  1515 N North Park Ave, Chicago, IL 60610
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  /18

  $4,990,000 New Construction

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

  Chicago, IL 60614

  Super Rare Extra-wide 26 ft lot custom new home on a beautiful one-way tree lined street created by the Savane Design and Build team, this home offers 6+ bedrooms, 5 1/2 baths, state-of-the-art luxury finishes, expansive indoor & outdoor living spaces, lavish master suite, and 3 car parking. Options include a raised rear yard, breezeway, wine cellar, sport court, in-home pool/hot tub, and 5-stop

  Tom Moran @properties Christie's International Real Estate

  Chicago, IL 60614
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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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  /67

  $4,850,000

  • 9 Beds
  • 8 Baths

  Unlisted Address

  Once in a lifetime opportunity to own a true urban oasis w/majestic renovated grey stone on 104'x126' vast city compound w/potential income from charming coach house and a 2BR/2BA garden unit in front half of basement overlooking picturesque garden in the desirable Bucktown neighborhood. This breathtaking dwelling was meticulously restored to celebrate the original fretwork, cove moldings, oval

  Jeffrey Lowe Compass

  Unlisted Address
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  /67

  $4,850,000

  • 7 Beds
  • 6.5 Baths

  1646 N Leavitt St, Chicago, IL 60647

  Once in a lifetime opportunity to own a true urban oasis with majestic renovated greystone on 104'x126' vast city compound with charming coach house overlooking picturesque garden in the desirable Bucktown neighborhood. This breathtaking dwelling was meticulously restored to celebrate the original fretwork, cove moldings, oval leaded glass windows, ceiling medallions, oak fireplaces w/antique

  Jeffrey Lowe Compass

  1646 N Leavitt St, Chicago, IL 60647
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  /48

  $4,850,000

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

  1219 W Madison St Unit PH, Chicago, IL 60607

  An exceptional opportunity to own a luxury private residence with built-in passive income in the heart of the West Loop. 1219 W. Madison offers a rare combination of residential living paired with two income-producing commercial storefronts on coveted Madison Street. This 8,490+ square foot mixed-use property is ideally situated on coveted Madison Street and offers exceptional flexibility for

  Jovanka Corazzina @properties Christie's International Real Estate

  1219 W Madison St Unit PH, Chicago, IL 60607

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