Chicago, IL Homes for Sale with Rooftop Deck

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  /20

  $299,000

  • 1 Bed
  • 1 Bath
  • 826 Sq Ft

  1400 S Michigan Ave Unit 2405, Chicago, IL 60605

  Tenant occupied until July 31,2026. Tenant would like to stay on in the unit if owner would be interested. South Loop, well-maintained 1 Bed / 1 Bath + Den in luxury Michigan Avenue Tower II. This is one of the largest 1-Bed unit in the building. Recent updating includes: Freshly painted throughout, new bedroom carpet, new furnace, new lighting, new ceiling fan. Living / dining open floor plan.

  Gina Majetic Furey Baird & Warner

  1400 S Michigan Ave Unit 2405, Chicago, IL 60605
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  /34

  $730,000

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft

  Unlisted Address

  Experience elevated urban living in this rarely available stunning southeast corner unit, showcasing sweeping city vistas through expansive floor-to-ceiling windows in every room. This sophisticated home features a beautifully appointed kitchen with an oversized peninsula-perfect for both entertaining and everyday dining-offering abundant counter space and seating. Premium stainless steel

  Rachel Vecchio Baird & Warner

  Unlisted Address
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  /38

  $825,000

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

  334 N Jefferson St Unit A, Chicago, IL 60661

  Welcome to your private urban sanctuary where space, sunlight, and sophistication await you just steps away from the Fulton Market District. Located at Kenzie Station this approx. 2,400 sq ft end-unit townhome offers three bedrooms and three full bathrooms on multi levels w/ gorgeous hardwood floors throughout. Step through the slate-tiled foyer and discover an entry-level suite-ideal for a home

  Lisa Postell @properties Christie's International Real Estate

  334 N Jefferson St Unit A, Chicago, IL 60661
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  /35

  $789,000

  • 4 Beds
  • 3.5 Baths

  6213 S Ellis Ave, Chicago, IL 60637

  Located just three blocks from the University of Chicago, this elegant contemporary home is quietly tucked away on a charming tree-lined street. Spanning four levels, the residence offers gracious living spaces, sophisticated design, and effortless access to the vibrant shops, restaurants, and cultural destinations of the neighborhood. Inside, spacious bedrooms, generous closets, and meticulous

  Susan O'Connor Berkshire Hathaway HomeServices Chicago

  6213 S Ellis Ave, Chicago, IL 60637
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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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  /33

  $649,900

  • 4 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  3918 S King Dr Unit 1S, Chicago, IL 60653

  Summer in Chicago comes to life from your private garage rooftop deck in this extraordinary four-bedroom, 3.1-bath triplex that lives like a single-family home. This beautifully designed residence offers expansive multi-level living rarely found in boutique condominium buildings, combining sophisticated design, exceptional outdoor space, and thoughtful functionality within a solid all-masonry

  Jennifer Bell Fulton Grace Realty

  3918 S King Dr Unit 1S, Chicago, IL 60653
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  /27

  $475,000

  • 4 Beds
  • 2.5 Baths

  4559 S Michigan Ave Unit 45593, Chicago, IL 60653

  The Resurgence on Michigan Avenue - Where History Meets Modern Luxury. Step inside this beautiful 4 bed/2.1 bath condo, to soaring 10' ceilings and 8' doorways, creating an open, airy feel throughout. The primary suite is a retreat with a Rainshower Spa bathroom, heated floors, and upgraded lighting fixtures. Bathrooms: 75" fixed glass panel added to the Jack-and-Jill bath for a sleek finish.

  Carlas Gilbert Prince Realty Group LLC

  4559 S Michigan Ave Unit 45593, Chicago, IL 60653
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  /20

  $998,000

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

  1830 S Calumet Ave Unit 7G, Chicago, IL 60616

  Welcome to your 3 bed | 2.5 bath end-unit stunner in the desirable Prairie District Neighborhood in the heart of the South Loop - where family living meets skyline drama. Let's start at the top: your private rooftop with views of Soldier Field and downtown skyline. Game days? Fireworks? Concert nights? You've got front-row vibes without leaving home. Inside, hardwood floors throughout the living

  Kimberly Carmen Berkshire Hathaway HomeServices Chicago

  1830 S Calumet Ave Unit 7G, Chicago, IL 60616
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  /38

  $1,599,000 Open Sat 12PM - 2PM

  • 5 Beds
  • 5 Baths
  • 3,608 Sq Ft

  2154 W Erie St, Chicago, IL 60612

  Stunning newer-construction single-family home on one of West Town's best blocks, located within the Mitchell School District. Built in 2019, this 4BD + 1 flex room, 3.2BA home offers approximately 3,608 square feet of living space across three levels. The open floor plan features hardwood floors, oversized windows, and high ceilings. The kitchen includes quartz and walnut countertops, a large

  Jorge Romero Realty One Group Inc.

  2154 W Erie St, Chicago, IL 60612
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  /11

  $175,000

  • 1 Bed
  • 1 Bath
  • 776 Sq Ft

  3900 N Lake Shore Dr Unit 17G, Chicago, IL 60613

  Live steps from the water in this stylish 1-bed, 1-bath condo perched in a premier lakefront high-rise. The contemporary kitchen shines with stainless-steel appliances and a center island that doubles as the perfect gathering spot. An airy open-concept living room and cozy dining nook make the space feel both spacious and functional. Northern exposures bring in incredible natural light and frame

  Josh Stein Fulton Grace Realty

  3900 N Lake Shore Dr Unit 17G, Chicago, IL 60613
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  /49

  $1,945,000

  • 3 Beds
  • 4.5 Baths

  1125 W Monroe St, Chicago, IL 60607

  West Loop Dream Home. Enter through a private yard into a versatile multi-purpose room, ideal for a home theater, office, or 4th bedroom with a full bath. The second floor features a custom, eat-in kitchen with an extended breakfast bar, beverage fridge, trash compactor, and new lighting. Includes a rare private in-unit elevator and three ensuite bedrooms. The main level offers a living/dining

  Frank Christiano Skydan Real Estate Sales, LLC

  1125 W Monroe St, Chicago, IL 60607
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  /30

  $774,900

  • 3 Beds
  • 2 Baths

  1310 N Ritchie Ct Unit 27C, Chicago, IL 60610

  Presenting this stunning brand new gut renovated three bedroom unit in a prestigious location, on a high floor with stunning views, in the landmarked Ritchie Tower building. The newly redesigned floor plan provides a bright open space that has a chef's kitchen that opens to the living & dining areas for entertaining and family gatherings. The three bedrooms are generously sized and there are two

  Eamonn Stafford @properties Christie's International Real Estate

  1310 N Ritchie Ct Unit 27C, Chicago, IL 60610
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  /21

  $967,000 Open Tue 10AM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,756 Sq Ft

  850 N Lake Shore Dr Unit 306, Chicago, IL 60611

  Now over 50% closed and ready for immediate occupancy! One-, two-, and three-bedroom units available ranging from 1000-3700+ square feet. 306 is a 1756 sq ft north facing 2 bedroom + den residence with 9' ceilings and all new SS Bosch kitchen appliances and new, in-unit Whirlpool washer and dryer. 850 Lake Shore Drive, awarded Development of the Year, is a fully amenitized, beautifully renovated

  Michael Hampton Wolf Residential Group LLC

  850 N Lake Shore Dr Unit 306, Chicago, IL 60611
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  /30

  $299,999

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft

  40 E 9th St Unit 1005, Chicago, IL 60605

  Step into effortless city living in this well-maintained 2-bedroom, 1-bath condo, located on the 10th floor of a South Loop high-rise. Natural light fills the spacious living room, creating an inviting space for everyday living and entertaining, complemented by hardwood floors and clean, neutral finishes. The thoughtfully designed layout includes two comfortable bedrooms with plush carpeting and

  Kywana Ross United Real Estate-Chicago

  40 E 9th St Unit 1005, Chicago, IL 60605
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  /19

  $315,000

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft

  33 W Delaware Place Unit 10B, Chicago, IL 60610

  Investors only at this point; tenant occupied. Experience sophisticated city living in the heart of the Gold Coast at Delaware and Dearborn, with views of Washington Square Park. This east-facing residence is flooded with natural light through floor-to-ceiling windows and opens to a large private balcony, perfect for enjoying morning coffee and the morning sunrise. The home features a sleek

  Marc Kaufman Baird & Warner

  33 W Delaware Place Unit 10B, Chicago, IL 60610
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  /24

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,328 Sq Ft

  920 W Madison St Unit 901W, Chicago, IL 60607

  Phenomenal private outdoor space and great natural light in this heart of West Loop 2 bed/2 bath corner unit in an elevator building. Floor to ceiling windows, high ceilings, two fully enclosed bedrooms, split floor plan and open great room. Kitchen offers Metropolitan Grey cabinets, full height stone tile backsplash, double sink, stainless steel appliances, granite countertops and breakfast

  Scott Stavish @properties Christie's International Real Estate

  920 W Madison St Unit 901W, Chicago, IL 60607
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  /26

  $639,000

  • 2 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  737 W Washington Blvd Unit 3003, Chicago, IL 60661

  Spacious two level duplex condo offering 2 bedrooms and 2.5 bathrooms in the heart of the West Loop with east facing city views and a private balcony. The main level features an open living and dining area, kitchen, half bath, and in unit laundry. Upstairs includes a primary suite with an en suite bathroom and a second bedroom with a full bath conveniently located just outside the door. Full

  Emir Vulic Berkshire Hathaway HomeServices Chicago

  737 W Washington Blvd Unit 3003, Chicago, IL 60661
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  /24

  $137,700

  • Studio
  • 1 Bath

  6171 N Sheridan Rd Unit 1408, Chicago, IL 60660

  Back on Market, Refreshed & Move in Ready, with Price Reduction! Welcome to Granville Beach Condominiums, Home to Your Sunny, South Facing Edgewater Beach Studio Condo featuring Lake Michigan in your backyard! Situated 14 floors up with beautiful wood laminate floor, your view of the Beautiful Lake Michigan Sunrise & Sunset! 3 closets, a wall of windows, & a few short steps to the elevator. The

  Ellen Baren @properties Christie's International Real Estate

  6171 N Sheridan Rd Unit 1408, Chicago, IL 60660
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  /22

  $699,000 Open Tue 10AM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft

  850 N Lake Shore Dr Unit 508, Chicago, IL 60611

  Now over 50% closed and ready for immediate occupancy! One-, two-, and three-bedroom units available ranging from 1000-3700+ square feet. 508 is a 1,286 sq ft, north-facing 2-bedroom unit with a 12 x 8 multi-purpose den, 11' ceilings, plenty of closet space, all-new stainless steel Bosch kitchen appliances, and a new in-unit Whirlpool washer and dryer. 850 Lake Shore Drive, awarded Development of

  Michael Hampton Wolf Residential Group LLC

  850 N Lake Shore Dr Unit 508, Chicago, IL 60611
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  /18

  $489,000 Open Sat 11AM - 1PM

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

  4208 S Calumet Ave Unit 301, Chicago, IL 60653

  Three Exceptional Residences in a striking full-masonry, intimate three-unit building blending contemporary design with the stately rhythm of Bronzeville's historic streetscape. The architecture is modern yet timeless, pairing clean lines with generous scale and spaces designed for real life-easy entertaining, comfortable everyday living, and flexibility to suit your lifestyle. Each extra-long

  Michelle Browne @properties Christie's International Real Estate

  4208 S Calumet Ave Unit 301, Chicago, IL 60653
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  /19

  $480,000 Open Tue 10AM - 3PM

  • 1 Bed
  • 1 Bath
  • 974 Sq Ft

  850 N Lake Shore Dr Unit 607, Chicago, IL 60611

  Now over 50% closed and ready for immediate occupancy! One-, two-, and three-bedroom units available ranging from 1000-3700+ square feet. 607 is a 974 sq ft north facing 1 bedroom + den residence with 9' ceilings and all new SS Bosch kitchen appliances and new, in-unit Whirlpool washer and dryer. 850 Lake Shore Drive, awarded Development of the Year, is a fully amenitized, beautifully renovated

  Lisa McMillan Wolf Residential Group LLC

  850 N Lake Shore Dr Unit 607, Chicago, IL 60611
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  /23

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,923 Sq Ft

  1653 N Parkside Ave, Chicago, IL 60639

  Welcome to 1653 N Parkside Avenue, a classic Chicago bungalow located in the Austin community offering charm, space, and future potential. The main level features a welcoming foyer entry, a bright living room with a gas fireplace and beautiful stained-glass windows, and a formal dining room ideal for entertaining. Just off the dining room is a versatile bedroom with double doors and convenient

  Camille Harris Coldwell Banker Realty

  1653 N Parkside Ave, Chicago, IL 60639
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  /32

  $2,600,000

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

  530 W Dickens Ave Unit 401, Chicago, IL 60614

  Set in an absolute A+ Lincoln Park location, this duplex-up penthouse is located in a coveted elevator building on a quiet, tree-lined street. Occupying the entire top floor, the residence offers rare 360-degree city views and exceptional natural light throughout. Designed with a refined modern aesthetic, this one-of-a-kind home features expansive open-concept interiors and multiple private

  Emily Sachs Wong @properties Christie's International Real Estate

  530 W Dickens Ave Unit 401, Chicago, IL 60614
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  /43

  $2,295,000 New Construction

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

  4844 N Hermitage Ave, Chicago, IL 60640

  On a sprawling 165-foot-deep lot stands this brand-new 6-bedroom, 4.5-bath home. From the massive rooftop deck and covered back patio to the suburban-style 1,500 square foot basement built for a rec room, gym, movie lounge, and guest stays, this residence offers features like radiant heated floors and functionality unmatched in today's market. The gourmet kitchen is a true centerpiece, with

  Joel Halperin Compass

  4844 N Hermitage Ave, Chicago, IL 60640
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  /2

  $3,750,000 New Construction

  • 7 Beds
  • 6.5 Baths
  • 6,304 Sq Ft

  548 W Oakdale Ave, Chicago, IL 60657

  A stunning transformation by Environs is underway behind this timeless historic facade. This full gut renovation will live like new construction with a reimagined modern, highly functional floor plan. Set on an extra-long lot, the home will offer 6,300+ square feet, 7 bedrooms, and 6.5 baths. An open First Floor flows effortlessly from front to back, anchored by a sleek Kitchen with oversized

  Kevin Wood @properties Christie's International Real Estate

  548 W Oakdale Ave, Chicago, IL 60657
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  /27

  $450,000

  • 2 Beds
  • 2 Baths

  3660 N Lake Shore Dr Unit 1613, Chicago, IL 60613

  Get ready to Enjoy STUNNING UNOBSTRUCTED VIEWS of the lake, city and harbor from this 16th floor, renovated, 2BR/2BA corner unit with GARAGE SPACE included in the price! This 2BR floor plan offers wall to wall views in every direction, luxury vinyl floors, a fabulous chef's kitchen with plenty of prep space, a walk-in Pantry, natural stone countertops, crisp white cabinetry, all NEW

  Cathryn Browne CB Real Estate LLC

  3660 N Lake Shore Dr Unit 1613, Chicago, IL 60613
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  /16

  $550,000 New Construction

  • 3 Beds
  • 2.5 Baths

  6414 N Francisco Ave Unit 101, Chicago, IL 60645

  This stunning duplex residence is a brand-new 3-bedroom, 2.5-bathroom home thoughtfully designed for modern living and comfortable entertaining. The main level features an open, inviting layout ideal for hosting, while the lower level offers a quiet, private retreat with well-appointed bedrooms. Flooded with natural light, the home showcases luxury modern finishes throughout, including engineered

  Joel Halperin Compass

  6414 N Francisco Ave Unit 101, Chicago, IL 60645
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  Price To Be Determined New Construction

  • 4 Beds
  • 3 Baths
  • 2,190 Sq Ft

  Unit 104 Plan at Seven on Elm Residences, Chicago, IL 60610

  Cabrini, LLC Builder

  505 W Elm Estate Unit 39402931, Chicago, IL 60610
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  /48

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,750 Sq Ft

  940 W Glenlake Ave Unit 19C, Chicago, IL 60660

  Experience breathtaking, unobstructed lake views from every room in this fully renovated 2-bedroom, 2-bathroom Edgewater condo. No detail was overlooked - this stunning home was completely gutted and upgraded with all new windows, air conditioners, heated floors, and designer finishes throughout. The modern kitchen boasts quartz countertops, a large island with extra storage and seating, and a GE

  Holly Mateer @properties Christies International Real Estate

  940 W Glenlake Ave Unit 19C, Chicago, IL 60660
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  /20

  $1,300,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,269 Sq Ft

  2235 W Oakdale Ave Unit 33-D, Chicago, IL 60618

  NOW UNDER CONSTRUCTION! Introducing Residence 33-D at RiverWard - a stunning property set within a collection of 35 new construction, extra-wide row homes tucked along the north branch of the Chicago River. Perfectly situated in an idyllic location and with access to Southport, Roscoe Village, and the expressway, this exclusive cul-de-sac community will deliver contemporary new construction row

  Cory Robertson Jameson Sotheby's Intl Realty

  2235 W Oakdale Ave Unit 33-D, Chicago, IL 60618
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  /34

  $2,797,500 New Construction

  • 6 Beds
  • 8 Baths
  • 5,000 Sq Ft

  2457 W Byron St, Chicago, IL 60618

  Exquisite new construction luxury home in Chicago's North Center. Discover unparalleled modern living in this brand new 2026 construction masterpiece, meticulously designed for sophistication, entertaining, and comfort. This expansive residence features 6 bedrooms each boasting its own en suite bathroom, ensuring privacy and convenience for family and guest alike. The primary kitchen presents a

  Christopher Zaccaro CV Estates, LLC

  2457 W Byron St, Chicago, IL 60618
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  /42

  $1,850,000

  • 5 Beds
  • 7 Baths
  • 8,800 Sq Ft

  3214 S Canal St, Chicago, IL 60616

  Presenting an extraordinary traditional single-family residence, constructed in 2007, this home is a true architectural gem. Spanning an impressive 8,800 square feet and situated on a generous double lot measuring 50' x 125' (6,250 square feet), it offers an abundance of space for both relaxation and entertainment. Crafted with full masonry brick, limestone, and steel, this residence is adorned

  Chaz Walters Coldwell Banker Realty

  3214 S Canal St, Chicago, IL 60616
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  /11

  $997,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 3.5 Baths

  3245 S Calumet Ave, Chicago, IL 60616

  Fourteen On The Boulevard is a striking new rowhome development that masterfully blends the influence of the timeless elegance of 19th-century architecture with the comfort and sophistication of contemporary city living. Nestled along one of Chicago's historic boulevards, these 14 bay-windowed homes enhance the surrounding late-1800s streetscape while offering every modern convenience. Each

  Michelle Browne @properties Christie's International Real Estate

  3245 S Calumet Ave, Chicago, IL 60616
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  /79

  $3,999,000

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

  53 E Division St, Chicago, IL 60610

  Classic in style and transitional in design, 53 E. Division St. is a 7,500-square-foot, 5 bed/9 bath luxury home in the heart of the Gold Coast with four private outdoor spaces and a rare attached garage. One of the only residential works by famed architect Jarvis Hunt, located steps from Oak Street Beach and moments from the Mag Mile, the renovated Beaux-Arts exterior is a masterpiece of ornate

  Tim Salm Jameson Sotheby's Intl Realty

  53 E Division St, Chicago, IL 60610
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  /28

  $4,500,000

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

  2044 N Fremont St, Chicago, IL 60614

  Welcome to living fabulous on Fremont! Built by AK Custom Homes in 2021, this home is situated on your standard 25X125 lot in the heart of Lincoln Park. With a short walk to all Armitage and Halsted have to offer, you won't want to miss this incredible luxury opportunity. Grab your favorite coffee from La Colombe or a truffle from Hotel Chocolat just down the block! This 6 bedroom, 6.1 bath home

  Danielle Dowell Berkshire Hathaway HomeServices Chicago

  2044 N Fremont St, Chicago, IL 60614
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  /33

  $1,100,000

  • 5 Beds
  • 3 Baths
  • 3,514 Sq Ft

  Unlisted Address

  Expansive 5 true bedrooms (2 up , 3 down) duplex by Halcyon Builders (2019 Build). Location and zoning allows for 3500+ sq ft of interior space. Exemplary entertaining space both indoors and out with nice separation between public and private spaces. Room for a large dining room table, home gym, home office AND recreation room, you will not quickly run out of options. Bedrooms all accommodate

  Jennifer Lapins @properties Christie's International Real Estate

  Unlisted Address
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  /26

  $179,900

  • Studio
  • 1 Bath
  • 500 Sq Ft

  260 E Chestnut St Unit 606, Chicago, IL 60611

  This stunning updated studio apartment boasts a modern and elegant design, featuring sleek dark hardwood floors and premium stainless steel appliances in the kitchen. The expansive bathroom provides a luxurious feel, while the spacious closets offer ample storage. Situated in a full-amenity building, residents enjoy the convenience of an on-site commissary, perfect for everyday essentials. The

  Kurt Merrill Baird & Warner

  260 E Chestnut St Unit 606, Chicago, IL 60611
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  /32

  $2,690,000

  • 4 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  37 E Elm St, Chicago, IL 60611

  An exceptional residence in the iconic Gold Coast, this historic Potter Palmer home on coveted Elm Street seamlessly blends timeless architecture with refined modern updates. Offering four bedrooms and four-and-a-half baths, the home has been thoughtfully renovated with elevated, designer finishes throughout. The main level presents an expansive living and dining space ideal for both formal

  Meghan Luffred @properties Christie's International Real Estate

  37 E Elm St, Chicago, IL 60611
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  /41

  $825,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft

  5114 S Kenwood Ave Unit 3B, Chicago, IL 60615

  Introducing 5114 Kenwood - A rare opportunity for new construction condominium living in a boutique elevator building at the vibrant epicenter of Hyde Park. Perfectly positioned on Kenwood Avenue, one of Hyde Park's most desirable residential streets, 5114 Kenwood delivers the product long missing from the neighborhood: single-level, contemporary residences with exceptional private outdoor living

  Amanda McMillan @properties Christie's International Real Estate

  5114 S Kenwood Ave Unit 3B, Chicago, IL 60615
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  /36

  $1,595,000

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft

  2334 N Oakley Ave, Chicago, IL 60647

  Introducing 2334 N Oakley Avenue, a fully renovated single-family home in Bucktown featuring an expansive rooftop deck, detached 2-car garage, and luxury interior upgrades throughout. Perfectly situated on a quiet residential street just steps from top neighborhood amenities, this all-brick vintage home blends architectural character with modern design, premium finishes, and exceptional outdoor

  Carrie McCormick @properties Christie's International Real Estate

  2334 N Oakley Ave, Chicago, IL 60647

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