Duplexes for Sale in Chicago, IL

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  /48

  $549,900

  • 7 Beds
  • 2 Baths

  6111 S Eberhart Ave, Chicago, IL 60637

  Looking for what might be the best 2-flat in all of Chicago? This is the one you've been waiting for! Welcome to 6111 S Eberhart, a stately and beautifully maintained legal 2-flat located in the heart of red-hot Woodlawn, one of Chicago's fastest-growing and most iconic neighborhoods. This is a rare opportunity for either the savvy house hacker looking to live in one unit and rent the other, or

  

  Andrew Dorazio

  Dorazio Real Estate LLC

  (773) 917-0546

  6111 S Eberhart Ave, Chicago, IL 60637
• Explore Chicago

• 

  

  

  /21

  $315,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 3 Baths

  6328 S Drexel Ave Unit 1, Chicago, IL 60637

  Welcome to spacious and beautifully updated 5-bedroom, 3-bath duplex-down in Hyde Park Township, just minutes from the train and the future Obama Presidential Center. This home combines modern comfort with incredible flexibility - perfect for homeowners and investors alike. Main level features refinished hardwood floors (2024), fresh paint throughout, and a bright, open concept living space. A

  

  Scott Fishman

  Worth Clark Realty

  (872) 268-8157

  6328 S Drexel Ave Unit 1, Chicago, IL 60637
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  /31

  $500,000 Open Sat 1:15PM - 2PM

  • 4 Beds
  • 3 Baths

  2948 N Narragansett Ave, Chicago, IL 60634

  Presenting an exceptional opportunity in Chicago's Montclare neighborhood, this fully updated two-unit residential building blends investment stability with modern, luxury living. Originally constructed in 1920, the property has undergone comprehensive renovations including newer kitchens, baths, flooring, paint, and fixtures, resulting in a low effective age of just 20 years and a

  

  Cecil Sabu

  ALLURE Real Estate

  (312) 874-6303

  2948 N Narragansett Ave, Chicago, IL 60634
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  /27

  $399,999

  • 5 Beds
  • 2 Baths

  5459 W Walton St, Chicago, IL 60651

  HOT North Austin 2-flat perfect for first-time homebuyers or those seeking related living options. This well-maintained property features a top-level duplex offering 3 bedrooms, 1 bath, a spacious master bedroom with a walk-in closet, and a loft area on the upper floor. The first-floor unit includes 2 bedrooms, 1 bath, a separate formal dining room, and a decorative fireplace. Recent improvements

  

  Ericka Taylor

  Coldwell Banker Realty

  (312) 467-7897

  5459 W Walton St, Chicago, IL 60651
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  /39

  $1,500,000

  • Land
  • 0.35 Acre
  • $4,285,714 per Acre

  2948 N Narragansett Ave, Chicago, IL 60634

  Presenting a rare dual-parcel opportunity in Chicago's Montclare neighborhood, offering both a fully renovated two-unit residential income property and a high-visibility corner commercial site, creating a combined land assemblage of approximately 15,000+ square feet with 120 feet of frontage on Narragansett Avenue. Residential Income Property (Two-Unit Building) Originally constructed in 1920,

  

  Cecil Sabu

  ALLURE Real Estate

  (312) 313-3743

  2948 N Narragansett Ave, Chicago, IL 60634
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  /24

  $950,000

  • 4 Beds
  • 3 Baths

  1730 W Beach Ave, Chicago, IL 60622

  Calling all house hackers and savvy investors-this is a rare opportunity you don't want to miss. Located in the heart of Wicker Park, this fully turnkey, income-producing property, operating as a successful Airbnb (until 2/26/26), generating six figures in annual gross income. On 2/28/26 the building will be fully rented with 1 year leases. The expansive duplex-up unit features 3 bedrooms and 2

  

  Brandice Hampton

  Baird & Warner

  (872) 275-3209

  1730 W Beach Ave, Chicago, IL 60622
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  /22

  $500,000 Open Sun 12:30PM - 2:30PM

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft

  840 E 52nd St Unit 1E, Chicago, IL 60615

  Sun-filled and like new, this stunning 3-bedroom, 3.1-bath duplex condo in sought-after Hyde Park blends space, comfort, and style. A gracious entry foyer leads to an expansive living and sun room, perfect for everyday living and entertaining. The gourmet cherry kitchen boasts stainless steel appliances, an oversized island, pantry, cooktop, and vent hood. Dual primary suites feature spa-inspired

  

  Helen Sobel

  Baird & Warner

  (312) 500-4238

  840 E 52nd St Unit 1E, Chicago, IL 60615
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  /25

  $515,000

  • 6 Beds
  • 2 Baths

  2345 W Grenshaw St, Chicago, IL 60612

  Welcome to this recently updated 2 unit building with an unfinished basement locatedlocated in the heart of Tri-Taylor, just steps from the Illinois Medical District and University of Illinois Chicago campus. This prime location continues to attract strong demand from both owner occupants and renters seeking convenience, stability, and long term growth. Each spacious unit offers 3 bedrooms and 1

  

  Tina Hollins

  Coldwell Banker Realty

  (773) 985-2808

  2345 W Grenshaw St, Chicago, IL 60612
• 

  

  /24

  $855,000

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

  1636 W Warren Blvd Unit 1, Chicago, IL 60612

  Fantastic Location! Spacious duplex-down featuring 4 bedrooms and 3 bathrooms. The home offers a large kitchen with granite countertops and high-end stainless steel appliances. Enjoy a generous family room with a full bar, perfect for entertaining. Additional features include central HVAC, in-unit washer and dryer, camera system, tankless water heater, hardwood floors, fireplace, and private

  Matt Laricy Americorp, Ltd

  1636 W Warren Blvd Unit 1, Chicago, IL 60612
• 

  

  /65

  $975,000 Open Sat 1PM - 3PM

  • 9 Beds
  • 5 Baths

  1336 N Hamlin Ave, Chicago, IL 60651

  Discover newer construction in the heart of Humboldt Park with luxurious finishes and an inviting condo feel. Both first floor and second offer three bedrooms, kitchen, living room, including master bedroom with stunning master baths that offer separate showers and freestanding jacuzzi tubs. Main floor is currently utilized as a duplex down which offers additional bedrooms, full bath, and family

  Monica Gutierrez RE/MAX 10

  1336 N Hamlin Ave, Chicago, IL 60651
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  /25

  $457,900

  • 5 Beds
  • 2 Baths

  411 N Lawler Ave, Chicago, IL 60644

  Welcome to 411 N Lawler Ave, your new home & investment. Property Highlights: New Windows, New oversized , insulated & enclosed back porch (multi-season use & great for morning coffee) , New James Hardie Exterior Siding, New central air in both units, New furnaces & hot water heaters, New laminate flooring throughout both units, New quartz kitchen counter tops, Wrought Iron Fence in front & back,

  Camille Harris Coldwell Banker Realty

  411 N Lawler Ave, Chicago, IL 60644
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  /27

  $425,000

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

  1169 S Plymouth Ct Unit 118, Chicago, IL 60605

  Discover refined city living in this beautifully appointed 2-bedroom, 2.5-bath duplex located in the heart of Dearborn Park in the South Loop. Thoughtfully designed, this home features hardwood floors throughout the open-concept living and dining area. The well-equipped kitchen includes granite countertops, stainless steel appliances, and an expansive breakfast bar-perfect for everyday living and

  Matt Laricy Americorp, Ltd

  1169 S Plymouth Ct Unit 118, Chicago, IL 60605
• 

  

  /39

  $1,399,999

  • 6 Beds
  • 4 Baths

  1636 W Warren Blvd, Chicago, IL 60612

  Prime Location - Two-Unit Investment Property or Ideal Owner-Occupant Opportunity with Roof Deck! Unit 1 (Duplex Down - 4 Bed / 3 Bath): Spacious and beautifully designed, this duplex down offers an open, U-shaped kitchen with granite countertops and high-end stainless steel appliances. Enjoy a large family room with a full bar - perfect for entertaining. Additional highlights include hardwood

  Matt Laricy Americorp, Ltd

  1636 W Warren Blvd, Chicago, IL 60612
• 

  

  /22

  $499,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 2 Baths

  4045 N Southport Ave Unit 4045, Chicago, IL 60613

  Welcome to this light-filled 4 bedroom, 2 bathroom duplex down nestled in the coveted Southport Corridor. Set in a charming 1940s building, this home blends historic character with modern updates for comfortable city living. The first floor includes the kitchen with brand new stainless steel appliances, large dining and living area, full bathroom, and 2 bedrooms. Step into the lower level with 2

  David Betancourt Redfin Corporation

  4045 N Southport Ave Unit 4045, Chicago, IL 60613
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  /31

  $1,650,000

  • 3 Beds
  • 2.5 Baths

  1533 W Barry Ave Unit 2, Chicago, IL 60657

  Incredible opportunity to own this like-new construction duplex with 3 outdoor spaces in the heart of Lakeview, nestled within the highly coveted Burley School District. This exceptional 3 bedroom, 2.5 bath home lives like a single-family residence, offering designer finishes, expansive living spaces, and multiple private outdoor areas-including a show stopping private rooftop with skyline views.

  Alexandre Stoykov Compass

  1533 W Barry Ave Unit 2, Chicago, IL 60657
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  /23

  $775,000 Open Sun 10AM - 11:30AM

  • 6 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5830 N Lincoln Ave Unit 1S, Chicago, IL 60659

  Experience refined city living in this stunning new construction duplex-down condominium, ideally located just west of Lincoln Square in the highly desirable Peterson Park neighborhood. This expansive approximately 3,600-square-foot residence offers 6 bedrooms and 4 bathrooms, showcasing luxurious finishes throughout, including beautiful hardwood flooring and soaring 10-foot ceilings complemented

  Matt Laricy Americorp, Ltd

  5830 N Lincoln Ave Unit 1S, Chicago, IL 60659
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  /30

  $1,124,500

  • 3 Beds
  • 2.5 Baths
  • 4,800 Sq Ft

  711 N Milwaukee Ave Unit 2, Chicago, IL 60642

  MATTERPORT/3D VIRTUAL TOUR LINK AVAILABLE! Welcome to an incredibly rare mix of open space and timeless finishes that just don't exist anywhere else in the city. Minutes to FULTON MARKET & walkable to everything including public transportation, multiple parks, endless dining & entertainment options & all that WEST TOWN/RIVER WEST have to offer, this is an absolutely

  Mario Greco Compass

  711 N Milwaukee Ave Unit 2, Chicago, IL 60642
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  /34

  $399,900

  • 4 Beds
  • 2 Baths

  2211 N Lorel Ave, Chicago, IL 60639

  Strong cash-flow opportunity in the rapidly appreciating Belmont Cragin neighborhood. This two-flat includes two finished residential units, each offering 2-bedroom plus layouts with separate utilities - minimizing expenses and simplifying management from day one. The property features hardwood floors, functional floor plans, and several newer appliances. A large unfinished attic creates

  Matt Laricy Americorp, Ltd

  2211 N Lorel Ave, Chicago, IL 60639
• 

  

  /28

  $735,000 Open Sat 12PM - 2PM

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

  1707 S Jefferson St Unit 2, Chicago, IL 60616

  Experience the essence of modern luxury in this architecturally striking new construction duplex-up penthouse offering 3 bedrooms, 2.1 baths, and four incredible outdoor spaces-including a massive private rooftop with breathtaking city views. From the moment you enter, the superior craftsmanship and meticulous attention to detail are undeniable. Expansive ceiling heights and a highly coveted

  Michael Gerhardt RE/MAX Premier

  1707 S Jefferson St Unit 2, Chicago, IL 60616
• 

  

  /21

  $165,000

  • 2 Beds
  • 2 Baths

  3211 W Lexington St Unit 3B, Chicago, IL 60624

  ***Cash only, sold AS IS.*** Bright and modern 2-story condo in Homan Square, just steps from Douglas Park. This contemporary duplex townhome lives like a single-family home, offering two full levels of living space. The first floor features recently refinished hardwood floors throughout, creating an ideal setting for entertaining. Enjoy an open living and dining area that flows into a spacious

  Jacqueline Alter Redfin Corporation

  3211 W Lexington St Unit 3B, Chicago, IL 60624
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  /33

  $774,999

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

  847 N Hermitage Ave Unit C, Chicago, IL 60622

  Experience elevated city living in this one-of-a-kind duplex penthouse in the heart of East Village, offering sweeping skyline views and exceptional natural light from three exposures. With dramatic two-story windows, this residence lives like a single-family home in the sky. Designed for both entertaining and everyday comfort, the open-concept main level features a beautifully reimagined kitchen

  Matt Laricy Americorp, Ltd

  847 N Hermitage Ave Unit C, Chicago, IL 60622
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  /35

  $664,900

  • 2 Beds
  • 2.5 Baths
  • 2,474 Sq Ft

  100 E Walton St Unit 41DE, Chicago, IL 60611

  A rare opportunity to own a truly distinctive corner duplex penthouse in one of the city's most coveted locations. Offering approximately 2,500 square feet, this one-of-a-kind residence features two bedrooms plus a den/sunroom and 2.5 bathrooms, all perched above the Magnificent Mile. Flooded with natural light from dramatic floor-to-ceiling windows, the home showcases sweeping skyline and lake

  Alexandra Bernardi Jameson Sotheby's Intl Realty

  100 E Walton St Unit 41DE, Chicago, IL 60611
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  /33

  $900,000

  • 5 Beds
  • 4 Baths

  3036 N Kedzie Ave, Chicago, IL 60618

  Well-maintained building featuring two legal dwelling units, plus a separate third unit currently operating as a short-term rental. Ideal for investors or owner-occupants looking to offset expenses with supplemental income. The lower level offers additional finished space with strong potential for conversion to an ADU (Accessory Dwelling Unit) or future duplex-down expansion (subject to zoning

  Camie Cirrincione Redfin Corporation

  3036 N Kedzie Ave, Chicago, IL 60618
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  /27

  $825,000

  • 7 Beds
  • 4 Baths

  4813 S Prairie Ave, Chicago, IL 60615

  Incredible Investment or House Hack / Multi-Family Living Opportunity in Bronzeville! Welcome to 4813 S Prairie Ave - A beautifully maintained legal 3 flat Greystone with a partially finished garden unit. Ideal for owner-occupants, investors, or multi-generational living, this property blends classic Chicago architecture with modern conveniences. Each unit showcases light filled high ceilings,

  Lauren Castillo O W Auction Group LLC

  4813 S Prairie Ave, Chicago, IL 60615
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  /14

  $180,000

  • 4 Beds
  • 2 Baths

  6221 S Wolcott Ave, Chicago, IL 60636

  This is an AMAZING opportunity to bring your vision to life. This brick 2 flat features an updated 2nd floor with 2 bedrooms, a bonus room and deck, separate heat and central air. The basement and first floor is gutted to the studs. When you remodel the first floor and basement, you can duplex it or make the basement a separate living and entertainment space. Schedule your appointment today!

  Loretta Fields On Point Realty Pros LLC

  6221 S Wolcott Ave, Chicago, IL 60636
• 

  

  /18

  $394,500

  • 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
• 

  

  /13

  $435,000

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

  4953 S Michigan Ave Unit 7, Chicago, IL 60615

  Come tour this rarely available 5 bed / 3 bath duplex condo in Hyde Park Township. Renovated in 2001, this home offers a very generous floor plan, including, but not limited to, two spacious living spaces, large bedrooms and baths. Relax in the master suite or entertain in the lower level- there are unlimited opportunities to explore with this hidden gem. Kitchen comes equipped with beautiful

  Anais Fowler SIANA REALTY LLC

  4953 S Michigan Ave Unit 7, Chicago, IL 60615
• 

  

  /19

  $769,900

  • 10 Beds
  • 4 Baths

  6402 S Greenwood Ave, Chicago, IL 60637

  RARE WOODLAWN 3-FLAT Greystone with EXCEPTIONAL unit sizes & PREMIUM cash flow. Meticulously maintained by current owner with extensive recent upgrades including COMPLETELY RENOVATED laundry area & full plumbing overhaul. THE STANDOUT: Massive duplex unit (1st floor) - SIGNIFICANTLY LARGER than typical Woodlawn 3-flat conversions. Currently commanding TOP-OF-MARKET rent - PROVEN income, not

  Brittany Ramsey Keller Williams ONEChicago

  6402 S Greenwood Ave, Chicago, IL 60637
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  /38

  $985,000

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

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

  Own a Piece of History - Live Like It's Brand New. Welcome to an impeccably restored 1897 architectural treasure where vintage character meets modern luxury. This extraordinary 3,213 sq ft first-floor duplex offers the space and privacy of a detached home - without the maintenance and responsibility. This first-floor duplex blends historic charm with high-end modern finishes. Enter through a new

  Janice Corley RE/MAX Premier

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

  

  /16

  $530,000

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

  2304 W Jackson Blvd Unit 1E, Chicago, IL 60612

  Bright and spacious duplex-down with a chef's kitchen featuring quartz countertops and upgraded appliances. Enjoy direct access to a private 900+ sq ft deck from the main level. 3 bedrooms and 2 bathrooms are located on the lower level, with a half bath off the main-floor living area. Just a 5-minute walk to the Western Blue Line and close to the United Center, downtown, medical district, and

  Chloe Reynolds Compass

  2304 W Jackson Blvd Unit 1E, Chicago, IL 60612
• 

  

  /23

  $895,000

  • 3 Beds
  • 3 Baths

  858 W Diversey Pkwy Unit 1W, Chicago, IL 60614

  Situated in Lincoln Park, this all-brick, southwest-facing 3-bedroom duplex is flooded with light and features exceptional high-end finishes throughout. The expansive quartz kitchen is highlighted by Viking appliances, a custom backsplash, and abundant cabinetry. Gorgeous oak floors complement the first level of living, which includes a large living and dining space with a recently refinished

  Randy Nasatir @properties Christie's International Real Estate

  858 W Diversey Pkwy Unit 1W, Chicago, IL 60614
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  /32

  $299,900

  • 4 Beds
  • 5 Baths
  • 2,800 Sq Ft

  5555 S Everett Ave Unit B3-4, Chicago, IL 60637

  Located within a stones throw of the Science & Industry Museum as well as the lakefront, this stunning, duplex condo lives and feels more like a townhome than a condo with a floor plan unlike you have ever seen before! As you walk into the unit your jaw will drop with the dramatic two story living room that offers a fireplace, vaulted ceilings along with floor to ceiling windows with views of the

  Ryan Smith RE/MAX Premier

  5555 S Everett Ave Unit B3-4, Chicago, IL 60637
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  /26

  $800,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 5 Baths
  • 2,100 Sq Ft

  1947 W Diversey Pkwy Unit 101, Chicago, IL 60614

  Bright & spacious extra wide Lincoln Park 2016 construction duplex down with floor to ceiling windows in boutique seven-unit building. Sleek modern chef's kitchen with quartz countertops & backsplash, Bosch SS appliances including five burner cooktop, range hood, beverage refrigerator, built in espresso maker & custom LED lighted cabinetry with pull out pantry. Open floorplan features wide oak

  Mike Frank Keller Williams Preferred Realty

  1947 W Diversey Pkwy Unit 101, Chicago, IL 60614
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  /56

  $1,199,000

  827 N Fairfield Ave, Chicago, IL 60622

  Investment opportunity featuring a solid brick 4 unit main building & rehabbed 4 bedroom Coach house. Each unit in the main structure consists of 4 rooms, 2 bedrooms, and 1 bath, Hardwood floors throughout, Updated kitchens and baths & Newer windows. The main building offers common laundry and additional storage. Huge rehabbed 4-bedroom, 1.5-bath duplex-up coach house offering a spacious and

  Arden Fowler CHICAGO HANDSHAKE LLC

  827 N Fairfield Ave, Chicago, IL 60622
• 

  

  /21

  $8,495,000

  4742 S Michigan Ave, Chicago, IL 60615

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

  Karen Biazar North Clybourn Group, Inc.

  4742 S Michigan Ave, Chicago, IL 60615
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  /24

  $1,280,000 New Construction

  • 3 Beds
  • 2.5 Baths

  2246 W Lyndale St Unit 1, Chicago, IL 60647

  Modern Luxury in the Heart of Bucktown. We're proud to present a stunning duplex down featuring 3 bedrooms, 2.5 bathrooms, and a seamless blend of style, comfort, and functionality in one of Bucktown's most sought-after locations. Designed for effortless indoor-outdoor living, this home offers two private outdoor spaces: a huge covered rear deck off the dining room, and an exclusive rooftop deck

  James Sheehan Sheehan Real Estate

  2246 W Lyndale St Unit 1, Chicago, IL 60647
• 

  

  /21

  $468,000

  • 7 Beds
  • 3 Baths

  5215 W Van Buren St, Chicago, IL 60644

  This stunning Greystone sits on a quiet, tree-lined block and offers the perfect setup to owner-occupy while generating rental income. The spacious layout includes a desirable duplex-down unit, providing flexibility for comfortable living or multi-generational use. Thoughtful 2024 updates bring peace of mind and long-term value, including a new roof on both the property and garage, a new boiler

  Israel Dominguez Realty of America, LLC

  5215 W Van Buren St, Chicago, IL 60644
• 

  

  /35

  $275,000

  • 8 Beds
  • 3 Baths

  8112 S Exchange Ave, Chicago, IL 60617

  TWO FLAT + INLAW SUITE WITH SEPARATE ENTRANCES - SUPER LOW TAXES, TWO 3 BEDROOM UNITS. UPPER TWO UNITS HAVE HARDWOOD FLOORS. LARGE UNFINISHED ATTIC SPACE - POSSIBLE DUPLEX UP. COMMON AREA WASHER/DRYER.

  Joseph Konney Top Care Realty LLC

  8112 S Exchange Ave, Chicago, IL 60617
• 

  

  /33

  $425,000

  • 7 Beds
  • 2 Baths

  6961 S Eberhart Ave, Chicago, IL 60637

  Looking for a great investment or to live in? This is it. Beautifully updated and move-in ready, this vacant two-unit building offers the perfect opportunity to live in one unit and rent the other - or rent both and start cash-flowing immediately. The first-floor unit features 2 bedrooms and 1 bath, plus a rare duplex extension into the basement, giving you additional space for storage, office,

  Konstantin Shelegeda Inter Properties Inc

  6961 S Eberhart Ave, Chicago, IL 60637
• 

  

  /28

  $499,900

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

  3213 S Wells St Unit 1, Chicago, IL 60616

  Airy and spacious 3 bedroom, 2.5 bath duplex located in coveted Armour Square on tree lined block! Chef's kitchen with all stainless steel appliances and large entertaining island flows into sunlit living room with Juliet balcony and high ceilings. Primary bedroom suite is very roomy with attached bath, double sinks, separate walk in shower/tub, and walk in closet. Lower level features 2

  Nicole Pusateri Bricks Realty LLC

  3213 S Wells St Unit 1, Chicago, IL 60616

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