Duplexes for Sale in Chicago, IL

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  /33

  $525,000

  • 6 Beds
  • 3 Baths

  5317 W Van Buren St, Chicago, IL 60644

  Prime Investment Opportunity: Fully Renovated 2-Unit Duplex in the hot Austin neighborhood! Updated from top-to-bottom, this stunning 2-unit property delivers modern luxury, strong rental income potential, and that coveted Austin vibe. Perfect for house-hackers, investors, or owner-occupants who want to live in one unit and let the other help with the mortgage. Unit 1 - Duplex-Down 3 Beds & 2

  Eric Wicencyjusz eXp Realty

  5317 W Van Buren St, Chicago, IL 60644
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  /32

  $3,995,000

  • 5 Beds
  • 5.5 Baths
  • 4,949 Sq Ft

  900 W Washington Blvd Unit PHW, Chicago, IL 60607

  Discover the best of the West Loop in this top-floor duplex penthouse at 900 West Washington, an exclusive LEED Gold-certified boutique building of just 22 homes. Sweeping skyline views surround a wraparound terrace, while the elevator opens directly into a modern, sun-filled interior with radiant-heated concrete floors. With new designer lighting, this residence offers a warm yet contemporary

  Laura England Compass

  900 W Washington Blvd Unit PHW, Chicago, IL 60607
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  /24

  $579,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  4447 S Vincennes Ave Unit 3, Chicago, IL 60653

  Skyline Evenings Begin Here 3.99 Interest Rate Available - 4447 S Vincennes | Unit 3 Some residences simply feel different the moment you walk in. Unit 3 at Flats on Vincennes II offers approximately 2,200 square feet of refined duplex living in the heart of Bronzeville - where scale, craftsmanship, and thoughtful design come together effortlessly. Natural light pours through European

  Jennifer Bell Fulton Grace Realty

  4447 S Vincennes Ave Unit 3, Chicago, IL 60653
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  /16

  $53,000

  • 4 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  10611 S Cottage Grove Ave, Chicago, IL 60628

  MOTIVATED SELLER DUPLEX SOLD AS IS NEEDS TLC!! LOTS OF POTENTIAL!!! WELL SOUGHT AFTER PULLMAN

  TERRANCE WILLIAMS Terrance Williams

  10611 S Cottage Grove Ave, Chicago, IL 60628
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  /24

  $1,049,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  2341 W Belden Ave Unit 1, Chicago, IL 60647

  New construction duplex-down condominium offering 3 bedrooms and 2.5 bathrooms with high-end finishes and thoughtful design throughout. This spacious home blends indoor and outdoor living and includes a private garage rooftop deck with privacy fence and built-in speaker system, providing a rare outdoor extension ideal for everyday living and entertaining. The main level features an open-concept

  Damian Wojcik Chicagoland Brokers, Inc.

  2341 W Belden Ave Unit 1, Chicago, IL 60647
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  /2

  $335,000

  • 5 Beds
  • 3 Baths

  7810 S Green St, Chicago, IL 60620

  Beautifully Updated 2-Flat-Move-In Ready! This well-maintained 2-flat features a spacious first-floor duplex ideal for added living space or rental income, plus a bright second-floor unit with 2 bedrooms. Both units have been thoughtfully updated and are in move-in condition, offering modern finishes and comfortable layouts. Perfect for owner-occupants or investors looking for a turnkey property.

  Charles Martin O.D. Neal Realty Associates

  7810 S Green St, Chicago, IL 60620
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  /32

  $639,900 New Construction

  • 5 Beds
  • 4 Baths

  6543 S Langley Ave, Chicago, IL 60637

  6543 S Langley Ave | New Construction Duplex-Up | 3.99 Interest Rate Available Yes, you read that right. The rates many buyers thought were gone have made a return - and this high-design new construction residence in West Woodlawn proves you don't have to compromise architecture, comfort, or flexibility to secure something truly special. From the moment you step inside, the home feels intentional

  Jennifer Bell Fulton Grace Realty

  6543 S Langley Ave, Chicago, IL 60637
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  /25

  $849,000

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

  310 S Michigan Ave Unit 1900, Chicago, IL 60604

  Preferred North-East tier at exclusive Metropolitan Tower. This 3 Bed/ 3 Bath luxury corner unit with spectacular city, lake and park views. These units rarely come on the market! Windows in every room with protected east views of park and lake. Functional layout with drywall to the ceilings in each room and great wall areas for artwork. Home is approximately 2000 SF with 8 windows sitting

  Michael Gentile @properties Christie's International Real Estate

  310 S Michigan Ave Unit 1900, Chicago, IL 60604
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  /25

  $725,000 Open Sat 10AM - 12PM

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  816 N Wood St Unit 3N, Chicago, IL 60622

  Exquisite East Village penthouse now available! Ultra-bright and extra-wide this 2bed/ 2bath top floor duplex unit is set in a newer construction boutique walk-up building and invites you in to enioy open concept living with abundant space and natural light through its sunsoaked floor to ceiling windows. The chef's kitchen is a showstopper with sleek two-tone cabinetry, quartz countertops, a

  Robert Yoshimura Compass

  816 N Wood St Unit 3N, Chicago, IL 60622
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  /3

  $185,500

  • 6 Beds
  • 2 Baths

  11833 S Indiana Ave, Chicago, IL 60628

  Listing price $185,500 The seller does not represent or guarantee occupancy status. NO viewings of this property. Please DO NOT DISTURB the occupant. Drive by only. Duplex. 6 bedrooms and 2 bathrooms. AS IS, cash only sales with no contingencies or inspections. Buyer will be responsible for obtaining possession of the property upon closing. Property sold without contingencies, repairs,

  Val Laborevitch Realhome Services & Solutions, Inc.

  11833 S Indiana Ave, Chicago, IL 60628
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  /46

  $1,900,000

  • 8 Beds
  • 6 Baths

  1053 N Damen Ave, Chicago, IL 60622

  Completely rehabbed in 2022. Brick 2-flat plus a fantastic updated coach house above a 2-car garage. The owner's duplex-down features 4 bedrooms and 3.5 bathrooms. High end finishes and vintage touches throughout. The large kitchen with an island opens up to a living/dining area with a fireplace. Gorgeous powder room off the main living area with a vessel sink and venetian plaster wall. En-suite

  Lucas Blahnik @properties Christie's International Real Estate

  1053 N Damen Ave, Chicago, IL 60622
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  /25

  $699,900

  • 10 Beds
  • 5 Baths

  2335 W 21st St, Chicago, IL 60608

  Property sold as-is with existing tenants and violations of record. Cash preferred. Steps from Pink Line train boarding station and Western Ave. Large brick four story Building (3234 SF) with additional rear two story brick coach house that has central heating and spiral staircase that leads to lower level. Front building offers a four bed room garden owner occupied apt with potential to duplex

  Jesse Gomez Realmart Realty Inc

  2335 W 21st St, Chicago, IL 60608
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  /21

  $575,000

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft

  5121 S Kimbark Ave Unit 1E, Chicago, IL 60615

  Airy and spacious duplex down with 4 bedrooms, 3 baths, and parking for 2 cars. Open floor plan features living area with gas fireplace, large dining area, and stainless/granite kitchen. Two bedrooms and two full baths on the main level include a primary suite with luxury bath with whirlpool and separate shower. The main level laundry room with side-by-side washer dryer is conveniently located

  Cathy Deutsch @properties Christie's International Real Estate

  5121 S Kimbark Ave Unit 1E, Chicago, IL 60615
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  /23

  $310,000

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  5743 S Michigan Ave Unit 1S, Chicago, IL 60637

  Spacious 3 Bed, 3 Bath Duplex in Washington Park! Warm and inviting 3-bedroom, 3-bathroom duplex condo offering two levels of comfortable living in the heart of Washington Park. The open-concept main level features a generous living and dining area perfect for entertaining plus a modern kitchen with sleek finishes and ample cabinet space. Primary suite includes a private bath and great closet

  Tene' Gray Real People Realty

  5743 S Michigan Ave Unit 1S, Chicago, IL 60637
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  /11

  $1,200,000 New Construction

  • 3 Beds
  • 2.5 Baths

  2023 W Augusta Blvd Unit 3E, Chicago, IL 60622

  We are excited to introduce 2023 W Augusta, Ukrainian Villages newest boutique luxury development. Built by highly experienced developers, Castleview Construction, this five unit building sits on an extra wide 48 foot lot, providing expansive open floor-plans and exceptional natural light. The Duplex Up Penthouse units consist of Three large bedrooms and 2 1/2 bathrooms with full private roof

  Andrew Thurston Sheehan Real Estate

  2023 W Augusta Blvd Unit 3E, Chicago, IL 60622
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  /16

  $584,900

  • 6 Beds
  • 4 Baths

  440 N Monticello Ave, Chicago, IL 60624

  This 2-unit multi-family residence with boulevard views, includes two 3-bedroom units and has a 1st floor unit that is a DUPLEX-DOWN. This Brick-front building was built in 2010 at a location where city and greenspace meet; Central Park, Franklin Boulevard, and Garfield Square. Just steps away from the Garfield Park Conservatory and Green Line stop. A 25' x 120' fenced-in side lot is included in

  Lenore Repel ASAP Realty

  440 N Monticello Ave, Chicago, IL 60624
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  /15

  $650,000 New Construction

  • 3 Beds
  • 2.5 Baths

  6414 N Francisco Ave Unit 201, Chicago, IL 60645

  This top floor residence is a brand-new 3-bedroom, 2-bathroom duplex-up penthouse designed for modern living and effortless entertaining. All bedrooms are thoughtfully located on the upper level, creating a private retreat, while the main level is dedicated to entertaining with an open, airy layout on a wide lot. The home is filled with tons of natural light and features luxury modern finishes

  Joel Halperin Compass

  6414 N Francisco Ave Unit 201, Chicago, IL 60645
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  /24

  $579,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  4443 S Vincennes Ave Unit 3, Chicago, IL 60653

  Skyline Evenings Begin Here 3.99 Interest Rate Available - 4447 S Vincennes | Unit 3 Some residences simply feel different the moment you walk in. Unit 3 at Flats on Vincennes II offers approximately 2,200 square feet of refined duplex living in the heart of Bronzeville - where scale, craftsmanship, and thoughtful design come together effortlessly. Natural light pours through European

  Jennifer Bell Fulton Grace Realty

  4443 S Vincennes Ave Unit 3, Chicago, IL 60653
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  /45

  $1,699,000

  • 4 Beds
  • 4 Baths

  3034 N Greenview Ave, Chicago, IL 60657

  Great investment opportunity to own this money making 3-flat on a corner lot in highly desired Lakeview! Gorgeous 1st floor 2 bed/ 2 bath + den, duplex-down has lovely owners finishes with, crown molding, beautiful hardwood floors, stylish exposed brick with tons of natural light throughout, custom chef's kitchen with 42" white shaker cabinets, stainless steel appliances, mother-of-pearl

  Jennifer Mills Jameson Sotheby's Intl Realty

  3034 N Greenview Ave, Chicago, IL 60657
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  /21

  $459,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  4351 S Vincennes Ave Unit 2, Chicago, IL 60653

  Looking for a Bronzeville condo that actually lives like a home? Welcome to the Flats on Vincennes, an all-brick duplex that gives you the space, light, and privacy you desire. This large, two-level home offers an easy, functional layout with plenty of room to breathe. The open living and dining area is bright, ideal for hosting, relaxing, and of course, everyday living. The kitchen is modern and

  Naja Morris @properties Christie's International Real Estate

  4351 S Vincennes Ave Unit 2, Chicago, IL 60653
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  /19

  $726,000 New Construction

  • 6 Beds
  • 5 Baths

  5027 S Indiana Ave, Chicago, IL 60615

  OWNER-OCCUPIED BUYERS ONLY! QUALIFIES FOR 20,000 GRANT FROM THE COUNTY. ANOTHER PROJECT BY AN AWARD WINNING DEVELOPER - GT ALTERNATIVES LLC. This gorgeous 2 unit new construction was completed in February, 2026 and features 4 bedrooms and 3 bathrooms in the duplex down first floor unit with white shaker designer kitchen cabinets, a large peninsula, quartz counters, stainless steel appliances and

  Marika Kakhiani Pedestal Realty LLC

  5027 S Indiana Ave, Chicago, IL 60615
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  /35

  $850,000

  • 3 Beds
  • 3.5 Baths

  600 N Kingsbury St Unit 1902, Chicago, IL 60654

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

  Scott Newman Keller Williams ONEChicago

  600 N Kingsbury St Unit 1902, Chicago, IL 60654
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  /31

  $1,725,000 New Construction

  • 4 Beds
  • 4.5 Baths

  3617 N Magnolia Ave Unit 1, Chicago, IL 60613

  We're excited to present this incredibly rare opportunity to completely customize your own 30ft wide duplex down in the heart of Southport Corridor. Nestled on picturesque Magnolia and situated in the Top Rated Blaine school district, this home will offer four bedrooms, four and 1/2 baths, exceptional private outdoor space and an expansive open floor plan with designer finishes throughout. Buyers

  James Sheehan Sheehan Real Estate

  3617 N Magnolia Ave Unit 1, Chicago, IL 60613
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  /36

  $999,000

  • 9 Beds
  • 4 Baths

  3323 W Potomac Ave, Chicago, IL 60651

  Turnkey legal 4-unit (Front building 2 units / Coach house 2 units) building in an amazing location. The front building features two (2) spacious 3-bedroom 1-bath units, while the rear brick coach house offers a further two (2) units. One 2-bedroom uni,t and a 1-bedroom unit-an ideal unit mix. Rear unit 1 potential to duplex down - framing in basement already completed. All units have been fully

  Sam Jenkins Jameson Sotheby's Intl Realty

  3323 W Potomac Ave, Chicago, IL 60651
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  /36

  $975,000

  • 6 Beds
  • 5 Baths

  4836 S Dorchester Ave, Chicago, IL 60615

  Stunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, where historical elegance is seamlessly integrated with contemporary living. This rare gem has been updated on the 1st level only to offer both classic charm and modern amenities perfect for short-term rentals generating great annual income. Bring your own touches for units 2. Unit 3 features a new kitchen

  Carlas Gilbert Prince Realty Group LLC

  4836 S Dorchester Ave, Chicago, IL 60615
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  /24

  $799,900 Open Sat 2PM - 4PM

  • 3 Beds
  • 3 Baths
  • 1,569 Sq Ft

  1901 W Armitage Ave Unit 1E, Chicago, IL 60622

  Stunning, fully updated corner 3-bedroom, 3-bath duplex-down in a prime Bucktown location near The 606 trail. Filled with natural light from bright northern and eastern exposures, this home offers generous room sizes, high ceilings, and an exceptional layout for comfortable living and entertaining. The spacious living and dining area features a stacked-stone fireplace, Juliet balcony, corner

  Millie Rosenbloom Baird & Warner

  1901 W Armitage Ave Unit 1E, Chicago, IL 60622
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  /29

  $579,900

  • 4 Beds
  • 3 Baths

  2336 W Taylor St, Chicago, IL 60612

  Two-unit building located in the highly desirable Tri-Taylor/Medical District. Unit 1 is a recently updated first-floor duplex with a finished basement, offering approximately 2,000 square feet of living space with 3 bedrooms and 2 full bathrooms. This unit features a bright and open kitchen and dining area with abundant natural light, recessed lighting throughout, fresh paint, and a brand-new

  Bartlomiej Trzop Coldwell Banker Realty

  2336 W Taylor St, Chicago, IL 60612
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  /58

  $2,490,000 New Construction

  • 11 Beds
  • 8 Baths

  Chicago, IL 60614

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

  Linda Levin Jameson Sotheby's Intl Realty

  Chicago, IL 60614
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  /24

  $225,000

  • 7 Beds
  • 2 Baths

  7438 S Stewart Ave, Chicago, IL 60621

  Value-Add 2-Family Opportunity - Priced Well Below Market! Don't miss this excellent opportunity to own a 2-family property with strong upside potential. Property Highlights: Two-family layout with separate heating systems for each unit Cosmetic updates needed on both the first and second floors - perfect for investors or buyers looking to add value Full basement The first-floor unit offers the

  Crystal Smith, REALTOR® Illinois Real Estate Partners

  7438 S Stewart Ave, Chicago, IL 60621
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  /24

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  847 W Ainslie St Unit 1E, Chicago, IL 60640

  Welcome to 847 West Ainslie Street unit 1E, an incredible property fully gutted and rehabbed in the heart of Chicago! This exciting project features seven modern condos with fresh, stylish designs, all while preserving the old charm of the building. You'll love the beautiful wooden central stairs and skylight at the top. You'll find five simplexes with 3 bedrooms and 2 bathrooms, a duplex with 4

  Susanna Cherubin-Delisi Compass

  847 W Ainslie St Unit 1E, Chicago, IL 60640
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  /9

  $3,500,000

  • 4 Beds
  • 4.5 Baths
  • 3,725 Sq Ft

  1447 N Dearborn St Unit 1S, 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 1S, Chicago, IL 60610
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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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  /13

  $350,000

  2911 W 25th St, Chicago, IL 60623

  Property was originally 4 Flat but has been gutted to the studs. Next door Lot at 2909 W. 25th St MLS#12461803 is included which has separate pin number. Seller will include Architectural Plans he had for rebuilt on each lot of 2 Duplex 2 units. Cash or Reno loan needed to purchase. Seller will not separate both lots must be sold together.

  Gloria Ortiz Real People Realty

  2911 W 25th St, Chicago, IL 60623
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  /2

  $44,000

  • Land
  • 0 Acre

  4206 S Wells St, Chicago, IL 60609

  RS-3 Zoned 25x122 VACANT LOT, perfect for your home or duplex investment build! There is an adjacent vacant lot on each side of the property for potential investment. RS-3 zoning permits -- per Chicago Zoning Ordinance 17-2-0200 -- Single-Family Detached Homes, Two-Flats. Convenient access to expressway, Walking distance to White Sox Stadium. New alley, and easy access to public transportation.

  Nayibe Garces Prello Realty

  4206 S Wells St, Chicago, IL 60609
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  /49

  $599,800

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

  1151 W 14th Place Unit 332, Chicago, IL 60608

  UNIVERSITY COMMONS RARE DUPLEX TOP FLOOR WITH SKYLINE VIEWS FROM BOTH LEVELS, DEEDED HEATED GAR INCLUDED. MAIN LEVEL WITH OPEN CONCEPT LAYOUT WITH ELEGANT STAINED FLOORINGS, WITH BEAUTIFUL WB F/P, NEW CARPET ON STAIRCASE, ALL SS APPLIANCES, SPACIOUS KIT WITH GRANITE COUNTERTOPS, STACKABLE LAUNDRY MACHINES. 2ND LEVEL OFFERS PRIVACY, COMFORT, TRANQUILITY AND BEAUTIFUL SKYLINE VIEWS FROM LARGE

  Arceli Antonio RE/MAX City

  1151 W 14th Place Unit 332, Chicago, IL 60608
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  /17

  $95,000

  • 4 Beds
  • 2 Baths

  12045 S Eggleston Ave, Chicago, IL 60628

  Calling INVESTORS or future HOUSE HACKERS! Bring your imagination to this beautiful 2-flat in West Pullman looking for the right owner to rejuvenate it! Each unit has 2 bedrooms and 1 bath room, large living room and dining room areas and eat in kitchens. Property has large basement with height perfect for duplex down from the 1st floor unit for more earning potential. Garage in back can be

  Veronica Tabb Coldwell Banker Realty

  12045 S Eggleston Ave, Chicago, IL 60628
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  /12

  $459,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  6755 N Hermitage Ave Unit 3, Chicago, IL 60626

  Introducing beautiful, quality-built new construction residences in an intimate eight-unit building in the heart of Rogers Park. There are six thoughtfully designed duplexes and two simplexes, creating a true boutique residential feel. This spacious and light-filled 3 bedroom/2.1 bath duplex-up showcases modern design and expert craftsmanship throughout. The homes feature hardwood floors,

  Natasha Motev Jameson Sotheby's Intl Realty

  6755 N Hermitage Ave Unit 3, Chicago, IL 60626
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  /34

  $829,900 Open House 3/29

  • 2 Beds
  • 2 Baths
  • 1,840 Sq Ft

  203 S Sangamon St Unit 310, Chicago, IL 60607

  Rare top floor duplex-up next to Mary Bartelme Park featuring 18 ft ceilings, private terrace, and dramatic natural light in the heart of the West Loop. This architecturally striking top floor two bedroom plus den, two bath residence features soaring 18 foot ceilings and expansive south facing windows that flood the home with natural light. The dramatic scale and volume create an airy lofted

  Maureen Chwarzynski Baird & Warner

  203 S Sangamon St Unit 310, Chicago, IL 60607
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  /8

  $1,175,000 New Construction

  • 3 Beds
  • 2.5 Baths

  1230 W Diversey Pkwy Unit 1, Chicago, IL 60614

  NEW CONSTRUCTION 3 BED/2.5 BATH DUPLEX CONDOMINIUM, ideally positioned on the border of Lakeview and Lincoln Park, and thoughtfully designed with high-end finishes and superior construction. With a wide-open main floor, this space is perfect for a party of any size. Upon entry, you find the formal living/dining area, to the right is the kitchen with a long island and high-end finishes and

  William Goldberg Fulton Grace Realty

  1230 W Diversey Pkwy Unit 1, Chicago, IL 60614
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  /29

  $485,000 Pre-Foreclosure

  • 7 Beds
  • 4 Baths

  4948 W Washington Blvd, Chicago, IL 60644

  Discover the potential of this beautifully renovated 2-unit property located in the vibrant Austin neighborhood of Chicago. A short distance from Columbus Park and major transit lines, ensuring easy access to local amenities and downtown Chicago. Recently updated in 2022, this building underwent an extensive renovation that includes: A complete gut renovation. Upgraded electrical and plumbing

  Alonzo Abron A Progeny Global LLC

  4948 W Washington Blvd, Chicago, IL 60644

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