Chicago, IL Homes for Sale under $500,000

• 

  

  

  /19

  $499,000

  • 1 Bed
  • 1 Bath
  • 661 Sq Ft

  211 N Harbor Dr Unit 1207, Chicago, IL 60601

  Modern 1BR at Cirrus Condominiums with Stunning Park Views, One Parking spot in the garage included. Lakeshore East's premier new lakefront residence. This beautifully appointed one-bedroom home (Residence 1207) features west-facing floor-to-ceiling windows with sweeping views of the new Cascade Park. One deeded parking space is included in the price. Interior finishes include wide-plank white

  Martha Lozano RE/MAX City

  211 N Harbor Dr Unit 1207, Chicago, IL 60601
• 

  

  

  /29

  $499,900

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft

  8 E Randolph St Unit 1401, Chicago, IL 60601

  Spacious, split 2bd/2ba with preferred northeast corner views! This great home features floor to ceiling windows with excellent Chicago River and lake views, high ceilings, and almost 1,460 square feet of living space. The spacious living room / dining room has plenty of room for hosting family and friends with a separate dining area near the balcony. The large private balcony is the perfect spot

  Michael Michalak RE/MAX 10 Lincoln Park

  8 E Randolph St Unit 1401, Chicago, IL 60601
• 

  

  

  /8

  $475,000

  • Land
  • 0.31 Acre
  • $1,532,258 per Acre

  5602 N Fairview Ave, Chicago, IL 60631

  .Exceptional build opportunity in Norwood Park within the highly sought-after Maine South High School District (D207). Rare oversized 85 x 168 corner lot offering incredible space, flexibility, and presence - ideal for a custom luxury new construction home. Located on a block experiencing continued new development, supporting strong long-term value and resale potential. Prime commuter location

  Oskar Wiatr Hometown Real Estate

  5602 N Fairview Ave, Chicago, IL 60631
• 

  

  /2

  $495,000

  • Land
  • 0 Acre

  5039 W Roosevelt Rd, Chicago, IL 60804

  16,625 SF of land 1 Corner lot & 4 interior lots. Located in the Roosevelt Road Pedestrian Oriented Zoning District. Zoning: RRP There are no restrictions on these lots outside of the existing zoning regulations

  Adam Schneiderman, SIOR Strauss Realty Ltd

  5039 W Roosevelt Rd, Chicago, IL 60804
• 

  

  

  /58

  $495,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  195 N Harbor Dr Unit 2709, Chicago, IL 60601

  Enjoy Views of Navy Pier, Lake Michigan, Harbor and Parks from this renovated 2 bedroom 2 bath with floor-to-ceiling windows at The ParkShore. Rarely available owned Self Park Garage parking is included! Incredible views from the living room and both bedrooms you will love. Walnut stained hardwood floors are in living and dining rooms, halls, and second bedroom; comfortable carpet in primary

  Janelle Dennis @properties Christie's International Real Estate

  195 N Harbor Dr Unit 2709, Chicago, IL 60601
• 

  /2

  $445,000

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

  3727 S Lowe Ave, Chicago, IL 60609

  This large single-family home boasts an expansive layout with over 2600+ square feet of finished living space, providing ample room for a large multi-generational or extended family to flourish. Stepping through the front door into the closeted foyer, you are greeted by a sprawling living room bathed in natural light streaming through the large windows. This residence a remarkable 10+ rooms,

  Mark Johns Gordon Realty Co.

  3727 S Lowe Ave, Chicago, IL 60609
• 

  

  /30

  $474,900

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

  9400 S Charles St, Chicago, IL 60643

  Beautiful Chicago bungalow rehab located at end of a quiet cul-de-sac in desirable Beverly. Open floor plan featuring 5 bd/3 baths with a first floor Master Suite with walk in closet and luxury bath. Chefs dream kitchen with SS appliances, sleek backsplash, custom 42" white shaker cabinets, granite counters, and stunning breakfast bar island. Brilliant hardwood flooring, recessed lighting,

  Michael Turk HomeSmart Realty Group

  9400 S Charles St, Chicago, IL 60643
• 

  

  /39

  $499,000

  • 3 Beds
  • 4 Baths
  • 3,200 Sq Ft

  4553 S King Dr, Chicago, IL 60653

  Experience modern city living in the heart of Historic Bronzeville with this beautifully designed 4 story, brick home on King Dr. This impressive, rare opportunity in the form of a townhouse offers three bedrooms, two full baths and two half baths with versatile living space across four levels. The first level provides the perfect flex space for a family room/entertainment area, home office or

  Toni Dortch Realty of America, LLC

  4553 S King Dr, Chicago, IL 60653
• 

  

  /10

  $400,000

  • 7 Beds
  • 5 Baths

  1473 W 77th St, Chicago, IL 60620

  Auburn Gresham Investment Opportunity with Value-Add Potential Spacious 4-unit building offering a total of 7 bedrooms and 5 bathrooms, ideal for investors or owner-occupants seeking strong income potential. The full basement features a finished recreation room perfect for entertaining or future tenant amenities, along with on-site laundry facilities. The property includes a rare 4-car garage and

  Sachet White Century 21 IMPACT

  1473 W 77th St, Chicago, IL 60620
• 

  

  /22

  $485,000

  • 2 Beds
  • 2 Baths

  Unlisted Address

  Renovated, south-facing top-floor 2-bedroom, 2-bath residence with a private balcony. The desirable split-bedroom layout offers excellent privacy. Features include newly refinished hardwood floors throughout and an open-concept kitchen with 42" custom cabinetry, granite countertops, and stainless steel appliances. Both bathrooms have been newly renovated, and the home offers two spacious walk-in

  Jian Fu Anasia Inc

  Unlisted Address
• 

  

  /23

  $415,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1000 N Lake Shore Dr Unit 2302, Chicago, IL 60611

  First Class renovation of corner 2 bedroom 2 bath on Iconic Lake Shore Drive. Welcome home to this light-filled, move-in ready residence featuring thoughtful finishes throughout. New floors, new kitchen cabinets, new stainless-steel appliances, stone countertops, steam shower, jacuzzi tub, built-ins and more. Full-service building offers 24/7 door staff, on-site engineer and property management

  Susan Dickman Berkshire Hathaway HomeServices Chicago

  1000 N Lake Shore Dr Unit 2302, Chicago, IL 60611
• 

  

  /16

  $420,000

  • 1 Bed
  • 1.5 Baths
  • 1,116 Sq Ft

  600 N Lake Shore Dr Unit 407, Chicago, IL 60611

  Embrace a warm and luxurious lifestyle in this tastefully and well-designed largest one bedroom floor plan, boasting cozy south-facing views of Navy Pier and the city. The spacious, upscale kitchen with granite countertops, stainless appliances, and breakfast bar opens to the living area and a wall of windows, ushering in the natural light. The distinctive dark hardwood flooring throughout the

  Stephanie Maloney HomeSmart Connect LLC

  600 N Lake Shore Dr Unit 407, Chicago, IL 60611
• 

  

  /21

  $400,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1631 S Michigan Ave Unit 604, Chicago, IL 60616

  Lakeside living in this top floor CORNER UNIT 2 bed/2 bath in South Loop! Natural light pours into living and dining rooms. Enjoy an updated kitchen, gorgeous balcony, hardwood floors, stainless steel appliances, gas fireplace, and oversized primary suite with plenty of space to work from home. This boutique elevator building with low HOA includes heat, internet, DirectTV, storage, bike room and

  Sera Sousley Keller Williams ONEChicago

  1631 S Michigan Ave Unit 604, Chicago, IL 60616
• 

  

  /18

  $490,000

  • 4 Beds
  • 2.5 Baths
  • 1,496 Sq Ft

  6325 N Whipple St, Chicago, IL 60659

  Spacious, raised brick ranch maintained in excellent condition. Formal living room; formal dining room; large eat-in kitchen. 3 bedrooms. 1 full bath and 1 half bath on main floor. New hardwood flooring in living room, dining room and bedrooms. Recent painting of all rooms and complete window treatments. 1 additional bedroom and1 full bath. Newer furnace; newer hot water heater; central air

  Eileen LeVee Next Century Real Estate, Inc.

  6325 N Whipple St, Chicago, IL 60659
• 

  

  /22

  $419,900

  • 10 Beds
  • 4 Baths

  Unlisted Address

  Discover this stunningly renovated two-unit building, updated in 2026, which boasts a wealth of modern features. The property includes new flooring, freshly painted interiors, sleek countertops, brand new appliances, updated lighting fixtures, and fresh baseboards and doors. With spacious closets and a rejuvenated ceiling, it truly feels like a brand new home. Conveniently located, both units are

  Andres Olaez Keller Williams ONEChicago

  Unlisted Address
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  /12

  $499,000

  • Land
  • 0 Acre

  1728 S Halsted St, Chicago, IL 60608

  ATTENTION, DEVELOPERS, BUILDERS, AND INVESTORS: don't miss this chance! A great location 2 lots of land (2 separate PINs with a combined 4522sf) for sale: it is located in the hot Pilsen area, just one block south of University Village, and where restaurants, bakeries, and banks, playgrounds, parks and bus stops are steps away; the land is zoned for B3-2 with 2.2 FAR ( buildable square footage is

  Daniel Kong Richland Global Inc

  1728 S Halsted St, Chicago, IL 60608
• 

  

  /27

  $485,000

  • 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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  /3

  $465,000

  • 4 Beds
  • 1.5 Baths
  • 8,000 Sq Ft

  6215 S Prairie Ave, Chicago, IL 60637

  Home needs complete rehab. Property is being sold AS-IS. Home is on an 8,000 SF lot and being sold along with 6219 S. Prairie 4,000 SF Vacant Land. 6223 S. Prairie 4,000 SF Vacant Land and 6227 S. Prairie, 8,000 SF. Great development opportunity. Room sizes are approximate. Please do your due diligence before making an offer. *Release of Liability form must be completed by all parties interested

  JeTaun Coleman Brakie Realty, Inc.

  6215 S Prairie Ave, Chicago, IL 60637
• 

  

  /10

  $400,000

  • 5 Beds
  • 2 Baths

  5523 W Huron St, Chicago, IL 60644

  WELCOME TO YOUR NEW HOME! BEAUTIFULLY UPDATED TWO FLAT WITH BASEMENT THAT CAN BE CONVERTED TO A THIRD APARTMENT. EACH SPACIOUS UNIT OFFERS SEPARATE LIVING, DINNING ROOMS! HARDWOOD FLOORING THROUGHOUT, STAINLESS STEEL APPLIANCES, WITH SPACIOUS BEDROOMS AND CLOSETS. FIRST FLOOR OFFERS TWO BEDROOMS AND THE SECOND FLOOR HAS 3 BEDROOMS. EACH FLOOR HAS IT'S OWN LAUNDRY HOOK-UPS AND SEPARATE GAS METERS.

  Eboni Mills EXIT Strategy Realty

  5523 W Huron St, Chicago, IL 60644
• 

  

  /37

  $409,777

  • 4 Beds
  • 3.5 Baths
  • 2,245 Sq Ft

  7335 S Greenwood Ave, Chicago, IL 60619

  Welcome to this fully renovated 4-bedroom, 3.5-bath home located in Chicago's desirable Greater Grand Crossing / Park Manor. This move-in-ready property blends modern finishes with generous living space and incredible potential. The main level showcases a designer kitchen featuring quartz countertops, shaker-style cabinetry, stainless steel appliances, elegant wainscoting, fresh neutral paint,

  George Medina Realty of America

  7335 S Greenwood Ave, Chicago, IL 60619
• 

  

  /23

  $459,000 New Construction

  • 2 Beds
  • 2 Baths

  3204 N Kostner Ave Unit 406, Chicago, IL 60641

  ALMOST 60 PRCNT SOLD! MOVE IN READY! Introducing 3204 Kostner! Unit 506 is a Premium penthouse with breathtaking unobstructed skyline views! We are pleased to present one of Avondale/Kilbourn Park's ONLY and its NEWEST condominium development! This best-kept-secret neighborhood has long awaited high-quality new condominium homes and they're here! Come early to select your home from 30 fantastic

  Karen Biazar North Clybourn Group, Inc.

  3204 N Kostner Ave Unit 406, Chicago, IL 60641
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  /27

  $498,000

  • 4,236 Sq Ft

  735 E 88th St, Chicago, IL 60619

  OWNER-FINANCING AVAILABLE. We are pleased to present for sale 735 E 88th, a six-unit multi-family investment property in the Chatham neighborhood of Chicago. The property is composed of six four-room 1-Bed/1-Bath apartments and a three-car garage that features updated electric, updated rear porch, central boiler heat (~8 years old), common hot water, newer windows, hardwood floors throughout,

  Gene Hart 33 Realty

  735 E 88th St, Chicago, IL 60619
• 

  /2

  $400,000

  • 7 Beds
  • 3 Baths

  8039 S Marquette Ave, Chicago, IL 60617

  If you're looking for investment property you found it! This 3 unit building is very spacious and has a number of updates.

  Tammy Jackson KM Realty Group, LLC

  8039 S Marquette Ave, Chicago, IL 60617
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  /30

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  218 S Western Ave Unit B, Chicago, IL 60612

  New to the Market!!!!! This beautifully spacious renovated Jackson Square Duplex condo is ready for you to call home. It features an open concept with 2 bedrooms and 2.5 bathrooms, along with stainless steel appliances, white shaker cabinets, quartz countertops and backsplash, recessed lighting, vinyl plank and ceramic flooring, in-unit laundry, central air, and a private garage space.

  Donna Baker Kale Realty

  218 S Western Ave Unit B, Chicago, IL 60612
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  /24

  $467,000

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

  155 N Harbor Dr Unit 403, Chicago, IL 60601

  Home Sweet Home - Unit 403 is a spacious 1400SF two bedroom/two bathroom home located in Lakeshore East at prestigious Harbor Point. Freshly painted, this thoughtful floorplan is set in the curve and provides stunning city and lake views from 15 total windows. The open floor plan offers a sun-filled galley kitchen with stainless steel appliances and generous cabinet storage. The separate dining

  Liane Pruchnik Berkshire Hathaway HomeServices Chicago

  155 N Harbor Dr Unit 403, Chicago, IL 60601
• 

  

  /18

  $449,900

  • 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
• 

  

  /38

  $429,900

  • 7 Beds
  • 2 Baths

  917 N Cicero Ave, Chicago, IL 60651

  Spacious and well-maintained multi-unit property, offering an excellent opportunity for both owner-occupants and investors. The first-floor unit features 2 bedrooms and 1 full bathroom, with a comfortable living area and functional layout. The second-floor unit offers 3 bedrooms and 1 full bathroom, providing generous space and flexibility. The basement adds additional value with 2 extra

  Edwin David Ruano Solaris Enterprises Inc

  917 N Cicero Ave, Chicago, IL 60651
• 

  

  /24

  $409,000

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

  1600 S Indiana Ave Unit 803, Chicago, IL 60616

  BRIGHT AND SPACIOUS 2-BEDROOM, 2-BATH WITH A DEN IN PRIME NORTHEAST CORNER UNIT WITH GARAGE PARKING AVAILABLE. NICE CITY AND LAKE VIEWS WITH FLOOR TO CEILING WINDOWS AND BALCONY. LARGEST 2 BEDROOM IN BUILDING. KITCHEN HAS GRANITE COUTERTOPS WITH AN BREAKFAST BAR, STAINLESS APPLIANCES. PRIMARY SUITE INCLUDES A WALK IN CLOSET, PRIVATE MASTER BATH WITH SEPARATE SHOWER & WHIRLPOOL TUB. BAMBOO

  Nam Seo Coldwell Banker Realty

  1600 S Indiana Ave Unit 803, Chicago, IL 60616
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  /25

  $410,000

  • 2 Beds
  • 2 Baths
  • 1,630 Sq Ft

  1052 W Balmoral Ave Unit 5F, Chicago, IL 60640

  Welcome to the Denifer - Historic building. 2 Bedrooms 2B 2 Bath. Spacious layout with generous room sizes, tall ceilings, hardwood floors throughout, original moldings and details, plus 3 exposures for an abundance of natural light. Large foyer greets you before living room with access to bright office or den. 2 spacious bedrooms, each with ample closets. Second bath ensuite with bedroom with 2

  Janice Moy-Wong Berkshire Hathaway HomeServices Chicago

  1052 W Balmoral Ave Unit 5F, Chicago, IL 60640
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  /9

  $424,900

  • 4 Beds
  • 2 Baths

  2731 S Whipple St, Chicago, IL 60623

  Welcome to 2731 s whipple chicago. This beautifully fully rehabbed two unit building is exactly what you've been looking for. NEW FENCE, NEW APPLIANCES, NEW ROOF, NEW TANKLESS WATER HEATER, NEW PLUMBING and so much more. This building offers 2 spacious units equipped with 2 bedrooms and 1 bath with brand new appliances including washers and dryers. Both units are currently occupied and have been

  Kayla Mychalczuk Coldwell Banker Realty

  2731 S Whipple St, Chicago, IL 60623
• 

  

  /25

  $485,000

  • 1 Bed
  • 1 Bath
  • 1,053 Sq Ft

  Unlisted Address

  The only corner one bedroom available in ParkView and nearly top floor! This desirable north and west corner home enjoys floor to ceiling windows throughout with amazing panoramic views of the Chicago River, the City skyline and even Lake Michigan and Ohio St. Beach! The open kitchen features 42" cabinets, stainless steel appliances, gas cooktop with built-in oven, granite counters and large

  Gail Spreen Jameson Sotheby's Intl Realty

  Unlisted Address
• 

  

  /19

  $489,000

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  4937 S Prairie Ave, Chicago, IL 60615

  Stunning, fully updated home in the heart of the Brownsville / Washington Park area, blending classic Chicago character with modern finishes throughout. The main level features an open and inviting layout with abundant natural light, beautifully refinished hardwood floors, and seamless flow between the living, dining, and kitchen spaces-ideal for everyday living and entertaining. The designer

  Landon Kelly Real Broker, LLC

  4937 S Prairie Ave, Chicago, IL 60615
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  /33

  $475,000

  • 8 Beds
  • 4 Baths

  3919 W Flournoy St, Chicago, IL 60624

  Turnkey investor opportunity featuring a 2-flat with a duplex-down and penthouse, ideal for both investors and owner-occupants seeking rental income. This recently updated property is designed for strong cash flow. The duplex-down offers 3 bedrooms on the main level plus 2 additional bedrooms below, while the penthouse includes 3 bedrooms and 1 full bath. Recent upgrades include new tuckpointing,

  Hakeem Sisney MNK Realty Professionals LLC

  3919 W Flournoy St, Chicago, IL 60624
• 

  

  /28

  $400,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1910 S Indiana Ave Unit 421, Chicago, IL 60616

  Sun-drenched and sophisticated, this 2-bedroom, 2-bathroom corner loft at Bank Note Lofts features soaring 14-foot ceilings, industrial beams, and bamboo hardwoods throughout. The open-concept kitchen boasts concrete counters, a large island, wine fridge, and a brand-new refrigerator, complemented by a new in-unit washer/dryer and a 2022 A/C unit. The primary suite offers a custom walk-in closet

  Anthony Angelos eXp Realty

  1910 S Indiana Ave Unit 421, Chicago, IL 60616
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  /5

  $499,900

  • Land
  • 0 Acre

  4337 W 16th St, Chicago, IL 60623

  Great opportunity to own a corner lot with two pins. Located on a busy street intersection. Zoning C1-2. Being sold as a package deal - together with 4351 W. 16th St. Endless options to open your next business!

  Jorge Luna REMAX Legends

  4337 W 16th St, Chicago, IL 60623
• 

  

  /5

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 1,140 Sq Ft

  8240 W Addison St, Chicago, IL 60634

  Don't miss this opportunity to own this adorable 3-bedroom, 2.1-bath home! Featuring a recently updated kitchen and a full finished basement, this home offers both comfort and functionality. Step outside to enjoy the cute backyard along an insulated 2-car garage, providing convenience and extra storage. Schedule your showing today - this one won't last!

  Griselda Anderson Realty of America, LLC

  8240 W Addison St, Chicago, IL 60634
• 

  

  /42

  $449,000

  • 5 Beds
  • 4 Baths
  • 3,300 Sq Ft

  7505 S Wolcott Ave, Chicago, IL 60620

  Welcome to 7505 S Wolcott Ave, a stunning full renovation that perfectly blends modern luxury with thoughtful design in the heart of Chicago's South Side. This expansive residence offers 5 spacious bedrooms and 4 full bathrooms, delivering the ideal layout for both comfortable living and elegant entertaining. Step inside to discover a bright, open interior featuring two custom fireplaces that

  Nia Crawford Realty of America, LLC

  7505 S Wolcott Ave, Chicago, IL 60620
• 

  

  /23

  $489,900

  • 1 Bed
  • 1 Bath
  • 1,100 Sq Ft

  505 N Lake Shore Dr Unit 501, Chicago, IL 60611

  Spectacular 1B/1B, fully remodeled West facing contemporary unit with unobstructed views overlooking the park and pool! Condo features Porcelanosa engineered wood flooring, contemporary cabinets with kitchen island and quartz countertops. Stainless steel appliances, custom interior Aria doors. LPT is a full amenity building offering an amazing 2.5-acre park on 3rd floor, state-of-the art health

  Anastasia Kokalias Oikos Realty LLC

  505 N Lake Shore Dr Unit 501, Chicago, IL 60611
• 

  

  /39

  $500,000

  • Studio
  • 1 Bath
  • 713 Sq Ft

  401 N Wabash Ave Unit 73C, Chicago, IL 60611

  Oversized studio on the 73rd floor of Trump Tower featuring stunning lake views. With over 700 square feet of living space, this bright residence offers floor-to-ceiling windows that capture beautiful views of Lake Michigan and fill the home with natural light. The functional layout provides ample space for both living and sleeping areas, making it an ideal in-town residence or weekend retreat.

  Chezi Rafaeli Coldwell Banker Realty

  401 N Wabash Ave Unit 73C, Chicago, IL 60611
• 

  

  /18

  $489,000 Open Sat 1PM - 3PM

  • 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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