Duplexes for Sale in Chicago, IL

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  /10

  $315,000

  • 5 Beds
  • 3 Baths

  7923 S Carpenter St, Chicago, IL 60620

  Located along a quiet, tree-lined street in Auburn Gresham, this timeless brick 2-flat has been lovingly maintained and is ready for its next chapter. Picture mornings on the screened in porch with coffee in hand. Step inside and you'll find two spacious units, each with sunlit living rooms, separate dining spaces, and eat-in kitchens waiting for your personal touch. The enclosed rear porches

  Armando Zires @properties Christie's International Real Estate

  7923 S Carpenter St, Chicago, IL 60620
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  /17

  $739,900

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

  1013 N Honore St Unit 1, Chicago, IL 60622

  Welcome to this spacious 3-bedroom, 2.5-bathroom duplex/condo located in the highly desirable West Town neighborhood. This property offers an excellent layout with ample living space and great potential for customization. Master bedroom and 1 1/2 bath located on main level. 2 bedrooms and 1 bathroom located in lower level. Enjoy outdoor living on the roof top deck, ideal for relaxing or

  Michael Olszewski Area Wide Realty

  1013 N Honore St Unit 1, Chicago, IL 60622
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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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  /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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  /10

  $355,000

  • 7 Beds
  • 3 Baths

  7100 S Prairie Ave, Chicago, IL 60619

  Great "live in" investment opportunity! This sturdy structured 2unit, features a duplex down from the 1st floor to the basement. The duplex unit has 4beds 2baths and the 2nd floor unit has 3beds 1bath. Located 3 blocks from the express way and surrounded by public transportation.

  Perdure Carter Realty of America, LLC

  7100 S Prairie Ave, Chicago, IL 60619
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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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  /20

  $499,000

  • 2 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  919 N Willard Ct Unit 1N, Chicago, IL 60642

  River West Duplex with an attached garage, 2 large outdoor entertaining areas and a great yard! Huge lower level family room with tall ceilings. Unit was recently rehabbed and in great condition! refinished oak hardwood floors and a gas fireplace in the living/dining room. New open kitchen featuring granite counters with a breakfast bar, maple cabinetry and newer stainless steel appliances. Large

  David Hunt Compass

  919 N Willard Ct Unit 1N, Chicago, IL 60642
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  /20

  $725,000

  • 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 proposed new construction is expected to be completed by mid March, 2026 and will feature 4 bedrooms and 3 bathrooms in the duplex down first floor unit with white shaker designer kitchen cabinets, a large peninsula, quartz counters,

  Marika Kakhiani Pedestal Realty LLC

  5027 S Indiana Ave, Chicago, IL 60615
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  /41

  $1,299,900

  • 4 Beds
  • 3.5 Baths

  200 E Delaware Place Unit 8-9C, Chicago, IL 60611

  To quote Oprah, "You get a CAR..." (with home sale)! Give yourself the ultimate holiday upgrade with the purchase of this home. The seller is offering a brand-new car of your choice with a value of up to $50,000 at closing, in addition of 1 year of electric charging in the building. One incredible purchase, two life upgrades. One-of-a-kind 4 bedroom, 3.5 bathroom duplex up in one Chicago's most

  Camille Canales Compass

  200 E Delaware Place Unit 8-9C, Chicago, IL 60611
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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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  /18

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,263 Sq Ft

  1808 S Michigan Ave Unit 7, Chicago, IL 60616

  Welcome to this beautifully renovated duplex in the South Loop's Prairie District. Located within a private gated community, this exceptional residence offers two levels of thoughtfully designed living space. Enter on the upper level to a bright and spacious open-concept living area featuring high ceilings, polished hardwood floors and expansive windows overlooking a quiet, landscaped courtyard.

  Sarah Valle Jameson Sotheby's Intl Realty

  1808 S Michigan Ave Unit 7, Chicago, IL 60616
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  /26

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft

  1949 N Whipple St Unit 1, Chicago, IL 60647

  Super cool 2Bed/2Bath + Den Duplex Down in Logan Square. This unit was gut rehabbed in 2007 and has been very well maintained ever since. You walk in to an absolute flood of sunlight in the living rom. Or wait! Is it the dining room? Do you then move the living room to the lower level? Or can you put it in den on the main level? Does the entire lower level become an enormous Primary Suite? The

  Andrew Tsoukalis @properties Christie's International Real Estate

  1949 N Whipple St Unit 1, Chicago, IL 60647
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  /58

  $2,990,000 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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  /59

  $450,000

  • 4 Beds
  • 3 Baths
  • 2,797 Sq Ft

  7730 N Paulina St Unit 1, Chicago, IL 60626

  Stunning 4BD/3BA Duplex in prime Rogers Park location with approximately 2797 sq. ft. This spacious and sun-filled, this beautifully updated duplex condo lives like a single-family home. Features include angled hardwood floors, tall ceilings, exposed brick, and generous room sizes throughout. East-facing sunroom with 7 windows is perfect as a home office or reading nook. The living room offers a

  Tedi Smola @properties Christie's International Real Estate

  7730 N Paulina St Unit 1, Chicago, IL 60626
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  /40

  $1,190,000

  • 4 Beds
  • 4 Baths
  • 3,213 Sq Ft

  1210 N Astor St Unit 1A, Chicago, IL 60610

  Vintage character and charm enhanced with complementary high end finishes, this impeccably renovated and restored 1897 classic maisonnette. Meticulous floor to ceiling improvements highlight this first floor duplex. Upon opening the massive mahogany front door of this 3213 sqft unit, one is immediately struck by the stunning wide-planked walnut hickory floors that seamlessly connect the rooms on

  Janice Corley RE/MAX Premier

  1210 N Astor St Unit 1A, Chicago, IL 60610
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  /24

  $240,000

  • 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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  /16

  $549,999

  • 6 Beds
  • 3 Baths

  3330 W Evergreen Ave, Chicago, IL 60651

  Whether you're a savvy investor or looking for the perfect live-in owner opportunity, this beautifully maintained 2-flat delivers space, style, and income potential in one of Chicago's most dynamic neighborhoods. Step inside and you'll find the character you've been craving-original woodwork, hardwood floors, and a classic built-in hutch that nods to the home's rich architectural history. But

  Joe Betancourt Betancourt Realty

  3330 W Evergreen Ave, Chicago, IL 60651
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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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  /54

  $1,350,000

  • 7 Beds
  • 4 Baths

  1839 W Henderson St, Chicago, IL 60657

  Prime Location Roscoe Village 2 Flat + Coach House. Perfect "Live-In" and/or investment property. Rehabbed 3br/2ba Coach House with Front Porch could be perfect as eventual owner unit. 2nd floor unit also freshly rehabbed and currently vacant set for a buyer to occupy. New kitchen and bathroom with in-unit washer/dryer. All 3 units have high ceilings, ample outdoor space & central air.

  John Materna CL3 Property Management

  1839 W Henderson St, Chicago, IL 60657
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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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  /46

  $2,880,000

  • 3 Beds
  • 3.5 Baths
  • 5,382 Sq Ft

  Unlisted Address

  Exquisitely modern with unparalleled panoramic views of the Chicago skyline and Lake Michigan, Residence 60M1 at 161 E. Chicago Avenue is a masterfully reimagined 3-bedroom, 3.5-bath duplex penthouse within the exclusive Olympia Centre. A 2023 full-scale renovation, this 5,400-square-foot corner home represents the pinnacle of luxury design, craftsmanship, and technology. The main level unfolds

  Tim Salm Jameson Sotheby's Intl Realty

  Unlisted Address
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  /20

  $389,000

  • 6 Beds
  • 3 Baths

  7208 S Eberhart Ave, Chicago, IL 60619

  Well-maintained 2-unit building featuring separate utilities, central air, and individual furnaces for each unit. The first-floor duplex-down offers spacious living areas with tall ceilings and two full baths. The lower level includes a full shower and a jacuzzi tub. Each unit includes its own washer and dryer, as well as an enclosed back porch. The property is equipped with exterior security

  Ebony Reaves Kale Realty

  7208 S Eberhart Ave, Chicago, IL 60619
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  /12

  $459,000 New Construction

  • 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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  /2

  $50,000

  • Land
  • 0.07 Acre
  • $714,286 per Acre

  824 W Garfield Blvd, Chicago, IL 60609

  Two Adjacent Lots for Sale - Prime Chicago Location! Address: 822-824 W Garfield Blvd, Chicago, IL 60609 Total Lot Size: Approx. 6,250 sq ft (each lot ~3,125 sq ft) Zoning: Residential - Vacant Land Ownership: Off-market, ready for transfer Why You'll Love It: Double the Opportunity: Two side-by-side lots offer flexibility for development-build two homes, a multi-unit, or a custom

  Spiro Georgelos Standard Properties Group LLC

  824 W Garfield Blvd, Chicago, IL 60609
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  /14

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  130 S Canal St Unit 9M, Chicago, IL 60606

  Welcome home to this spacious three-bedroom, 2.5-bathroom duplex in West Loop! This bright and airy condo offers amazing views you can enjoy from your private 300-square-foot terrace- perfect for hosting or relaxing. The main level features tall windows, high ceilings, and a sleek kitchen that flows into the living room, along with a versatile bedroom ideal for guests or a home office, plus a

  Angel Aguilar Homes Realty of Chicago Inc

  130 S Canal St Unit 9M, Chicago, IL 60606
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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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  /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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  /46

  $999,000

  • 4 Beds
  • 6 Baths
  • 4,000 Sq Ft

  1410 N State Pkwy Unit 27A, Chicago, IL 60610

  Incredible, one-of a kind corner duplex penthouse in an elegant boutique vintage building on fabulous tree-lined North State Parkway. This versatile floor plan offers two levels of expansive space, perfect for entertaining and comfortable living. The main level features a wide open light and bright living/dining space with multiple seating areas featuring gorgeous north and east views of the lake

  Emily Sachs Wong @properties Christie's International Real Estate

  1410 N State Pkwy Unit 27A, Chicago, IL 60610
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  /93

  $2,999,999

  • 5 Beds
  • 4 Baths

  116 N Willard Ct Unit PH01, Chicago, IL 60607

  BEST VALUE PENTHOUSE WITH PRIVATE ROOFTOP IN THE WEST LOOP! LAST 2 UNITS REMAIN IN THIS DEVELOPMENT. Tucked away on a quiet side street in the heart of Chicago's vibrant West Loop, this stunning new-construction duplex penthouse offers an unparalleled blend of luxury, space, and privacy. Spanning two expansive levels with over 1700 sq ft of private rooftop deck, this 5-bedroom + den/office,

  Sabina Szura Baird & Warner

  116 N Willard Ct Unit PH01, Chicago, IL 60607
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  /15

  $399,900

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  2235 N Tripp Ave, Chicago, IL 60639

  2235 N Tripp, Chicago - Gorgeous & Sunny 4BD/2BA Duplex Single Family Home in Hermosa! This beautifully updated duplex single-family home offers the perfect combination of space, style, and convenience. Updated eat-in kitchen with granite countertops and abundant cabinet space. Two full bathrooms featuring modern tile work and fixtures Four spacious bedrooms with generous closet space. Hardwood

  Ryan Casper eXp Realty

  2235 N Tripp Ave, Chicago, IL 60639
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  /22

  $639,000 New Construction

  • 3 Beds
  • 2.5 Baths

  3339 N Ridgeway Ave Unit 1N, Chicago, IL 60618

  All Brick and High-Quality New Construction in Prime Avondale location, by Masonry contractor/ Builder with 25+ years of experience. Located on a tree-lined street, boutique development on a double lot. This 3 beds 2.5 baths Duplex unit offers 2 levels of living space along with a spacious front balcony, the sleek design and attention to detail. Custom finishes throughout, an open kitchen with a

  Beata Sieczka New Home Realty Inc

  3339 N Ridgeway Ave Unit 1N, Chicago, IL 60618
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  /37

  $1,049,000

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

  1035 N Hermitage Ave Unit 3, Chicago, IL 60622

  Welcome to Residence 1035. An oversized and generous, 3 bedroom 2.1 bathroom duplex penthouse - better than new construction. Fully renovated over the course of more than years into a cohesive conversion of high-end elegance which parallels the look, feel and functionality of a custom single family home (boasting approx. 2800sf in total; spread over 1700sf inside & 1100sf outdoor spaces) //////

  Sue Tao Jameson Sotheby's Intl Realty

  1035 N Hermitage Ave Unit 3, Chicago, IL 60622
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  /31

  $610,000

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

  130 S Canal St Unit 9F, Chicago, IL 60606

  Stylish West Loop Duplex Condo - Modern Comfort & Convenience! Step into elevated city living with this stunning 2-bedroom, 2.5-bath duplex condo on the 9th and 10th floors of Metropolitan Place. The open living area shines with hardwood floors, fireplace, and dramatic floor-to-ceiling windows, while the beautifully updated kitchen is perfect for entertaining. The spacious primary suite offers a

  Sally Haynes Keller Williams ONEChicago

  130 S Canal St Unit 9F, Chicago, IL 60606
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  /37

  $850,000

  • 4,320 Sq Ft

  1314 W 18th Place, Chicago, IL 60608

  This is a great opportunity for a value add 6-unit brick building in Pilsen, ready for its next owner. It's a solid property that just needs some fixing up to reach its full potential. You'll find a good mix of units, including two 1-bed/1-bath apartments, three 2-bed/1-bath units, and a large 4-bed/2-bath duplex with its own laundry. The important updates are already done, with a roof less than

  Jose Salinas You Properties LLC

  1314 W 18th Place, Chicago, IL 60608

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