Investment - Homes for Sale in Chicago, IL

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  /10

  $370,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath

  726 N Troy St, Chicago, IL 60612

  ***Prime ADU opportunity! Ideal for adding a garden unit and potential coach house, offering multiple income streams and strong value-add potential under Chicago's new ADU guidelines.*** Incredible opportunity for homeowners, investors, or developers First floor has been fully gutted - ready for your vision Second floor is currently occupied will be out by end of March. Located in a prime Chicago

  

  Araceli Montalvo

  Extreme Realty LLC

  726 N Troy St, Chicago, IL 60612
• Explore Chicago

• 

  

  

  /20

  $499,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  3400 W Shakespeare Ave, Chicago, IL 60647

  Opportunity is knocking in one of Chicago's most sought-after neighborhoods! This 1960's solid brick ranch sits on a desirable South East corner lot in Logan Square, offering the perfect blend of character, location, and incredible upside. Whether you're looking for your next home or your next investment, this property is full of potential. Originally Built in 1960 with quality craftsmanship, the

  

  Cecille Plurad

  Coldwell Banker Realty

  3400 W Shakespeare Ave, Chicago, IL 60647
• 

  

  

  /19

  $68,900

  Open Sun 9AM - 12PM $31K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  6945 S Chappel Ave Unit 3A, Chicago, IL 60649

  Opportunity Just Got More Affordable here! If you've been waiting for the right combination of value, location, and potential, your patience just paid off. With a recent price modification, this condo now offers an even more compelling opportunity to own in one of Chicago's well-established South Shore communities. Featuring a comfortable layout designed for everyday living, this unit offers a

  

  Tamika Marks

  Trademarks & Associates

  6945 S Chappel Ave Unit 3A, Chicago, IL 60649
• 

  

  

  /50

  $509,900

  Pending

  • 6 Beds
  • 3 Baths

  1025 N Trumbull Ave, Chicago, IL 60651

  Spacious all-brick 2 flat featuring a fully finished garden-level unit, ideal for extended family living or generating additional rental income. Each unit offers 2 bedrooms and 1 bathroom, while Units 1 and 2 include a versatile bonus room perfect for a third bedroom, home office, or den. The first and second floor units are equipped with gas-forced air heating and central air conditioning for

  

  Rafay Qamar

  Real Broker LLC

  1025 N Trumbull Ave, Chicago, IL 60651
• 

  

  

  /20

  $489,000

  $10K PRICE DROP Pending

  • 9 Beds
  • 3 Baths

  11146 S Vernon Ave, Chicago, IL 60628

  YOUR NEXT INVESTMENT IS HERE!! This updated 3 unit property features 3 bed/1bath in each unit. All units have identical layouts.

  

  Bill Eliopoulos

  Cosmos Realty Investors, Inc.

  11146 S Vernon Ave, Chicago, IL 60628
• 

  

  /26

  $699,000

  • 6 Beds
  • 2 Baths

  3000 N Mason Ave, Chicago, IL 60634

  You have been waiting for this! Amazing brick 2 flat with 3 beds and 1 bath on each floor PLUS unfinished basement that is ready for additional space/storage/income. Building features new windows, fresh tuck-pointing, brand new kitchens and baths, new flooring, fresh paint and trim, each unit has its own central heating and cooling plus detached 2 car garage. Location is perfect, close to

  

  Jerzy Mastalerczyk

  Real Broker LLC

  3000 N Mason Ave, Chicago, IL 60634
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  /11

  $119,000

  $15K PRICE DROP

  • 1 Bed
  • 1 Bath

  953 E 61st St Unit 1E, Chicago, IL 60637

  Comfortable Condo Near the University of Chicago - Ideal for Living or Investing. This sunny, inviting condo sits just one block from the University of Chicago and offers unbeatable convenience to campus, the Red Line, JewelOsco, and everyday essentials. Whether you're looking for a personal home or a solid investment, this location delivers. Inside, enjoy natural light throughout, easycare

  

  Ericka Taylor

  Coldwell Banker Realty

  953 E 61st St Unit 1E, Chicago, IL 60637
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  /73

  $1,699,000

  • 5 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  5054 N Claremont Ave, Chicago, IL 60625

  Luxury living redefined in the heart of Lincoln Square. Completely transformed from top to bottom, this exceptional residence has been thoughtfully redesigned with new high-end finishes, exceptional craftsmanship, and timeless elegance throughout. Spanning approximately 3,800 square feet with 5 bedrooms and 4 bathrooms, every interior space has been reimagined to create a home that blends

  

  Mike Musa

  Keller Williams Preferred Rlty

  5054 N Claremont Ave, Chicago, IL 60625
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  /18

  $860,000

  $99K PRICE DROP

  • 11 Beds
  • 6 Baths

  1656 W Hollywood Ave, Chicago, IL 60660

  This remarkable building features a unique floor layout, with ample bedrooms and bathrooms. The property consists of two apartments, each with garden and in-law units. It offers plenty of storage space, a separate utility room, and a laundry area, along with rear parking availability. This property has great potential for investment and is conveniently located near shopping areas, restaurants,

  

  Maria Ortiz

  Kale Realty

  1656 W Hollywood Ave, Chicago, IL 60660
• 

  

  /59

  $399,900

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft

  1622 S Central Park Ave, Chicago, IL 60623

  Stunning Turnkey Gem in Chicago's Emerging North Lawndale Neighborhood ****Welcome to this beautifully reimagined single-family home, now available in Chicago's rapidly growing North Lawndale neighborhood. Thoughtfully renovated while preserving its charming 1920s vintage character, this distinctive residence offers a rare blend of historic charm and modern luxury-making it a true turnkey

  

  Edgar R. Guerrero

  REMAX Legends

  1622 S Central Park Ave, Chicago, IL 60623
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  /40

  $1,199,000

  • 4 Beds
  • 4 Baths

  1024 W 18th Place, Chicago, IL 60608

  Welcome to this rare double lot gem in the heart of Pilsen-featuring two updated units with exceptional versatility and strong investment potential. This well-maintained property blends modern upgrades with the charm and energy of one of Chicago's most vibrant neighborhoods. A brand-new roof was installed in June 2025. Each unit offers its own distinct style, making it ideal for multigenerational

  

  Lizette Esparza

  Smart Home Realty

  1024 W 18th Place, Chicago, IL 60608
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  /14

  $159,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,035 Sq Ft

  7147 S Green St, Chicago, IL 60621

  **Very Affordable Rehabbed Home in Englewood Chicago** that stands out as one of the best-looking properties on the block. This 4 bed, 2 full bath residence has been brought back to life offering incredible value in one of Chicago's most actively developing South Side corridors. What's new? Just about Everything. New drywall. New electrical. Freshly painted interior and exterior. Fully redesigned

  

  Mario Zelaya

  eXp Realty

  7147 S Green St, Chicago, IL 60621
• 

  

  /19

  $189,000

  $6K PRICE DROP

  • 3 Beds
  • 2 Baths

  7847 S Maryland Ave, Chicago, IL 60619

  Perfectly positioned in a residential neighborhood, use as an apartment upstairs with a business below, or, transform the current commercial space in to residential. Flexible building perfect for investment or personal use. Current use is a condo rental upstairs, hair salon and office (with separate hallway entrance) on first floor. Renters are on a month-to-month, both are long time tenants.

  

  Laraine Hanson

  Laraine Hanson

  7847 S Maryland Ave, Chicago, IL 60619
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  /35

  $439,000

  $11K PRICE DROP

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

  1516 S Wabash Ave Unit 1102, Chicago, IL 60605

  Landmark Lofts is an investor-friendly condo association, making this top-floor northeast-corner residence an exceptional opportunity for investors and owner-occupants. Based on estimated market rent for both the residence and deeded heated parking space, the property offers the potential for an upwards-of-6% capitalization rate, subject to buyer verification and operating assumptions. This

  

  Cecil Sabu

  ALLURE Real Estate

  1516 S Wabash Ave Unit 1102, Chicago, IL 60605
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  /23

  $369,990

  $15K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 826 Sq Ft

  420 E Waterside Dr Unit 1802, Chicago, IL 60601

  Experience elevated city living in the heart of Lakeshore East at 420 E Waterside Dr, Unit 1802. This beautifully maintained 1-bedroom, 1-bath residence offers breathtaking south-facing views of the lake, park, and iconic Chicago skyline through expansive floor-to-ceiling windows that fill the home with natural light. The open-concept floor plan is designed for both comfortable everyday living

  

  Cathy Wu

  AiHome Realty Group LLC

  420 E Waterside Dr Unit 1802, Chicago, IL 60601
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  /24

  $75,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  11519 S Kedzie Ave Unit 57, Merrionette Park, IL 60803

  Why Rent When You Can Own an End Unit with a Balcony to Call Your Own? Welcome to 11519 S Kedzie...where comfort, convenience, and affordability come together in this inviting end-unit 1-bedroom, 1-bath condominium. Whether you're purchasing your first home, downsizing, or adding to your investment portfolio, this condo offers a wonderful opportunity to enjoy low-maintenance living in a

  

  Tamika Marks

  Trademarks & Associates

  11519 S Kedzie Ave Unit 57, Merrionette Park, IL 60803
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  /39

  $350,000

  • 6 Beds
  • 2 Baths

  7214 S Saint Lawrence Ave, Chicago, IL 60619

  ***Buyer Agents Read Broker Remarks***Click on the virtual tour and step into a beautifully reimagined, oversized brick two flat nestled in the heart of Chicago's historic Greater Grand Crossing neighborhood. Fully renovated in 2023, this majestic property blends timeless Chicago architecture with modern craftsmanship and thoughtful design. The building offers high efficiency heating and cooling

  

  Angel Rosales

  PROSALES REALTY

  7214 S Saint Lawrence Ave, Chicago, IL 60619
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  /27

  $450,000

  Pending

  • 5 Beds
  • 2 Baths

  2835 W Wellington Ave Unit 2, Chicago, IL 60618

  Welcome to 2835 W Wellington, a stunning top-floor duplex up with a spacious, light-filled 5-bedroom, 2-bath condo. This square footage and flexibility are incredibly rare to find. Previously operated as a successful Air BnB, the unit has been designed for comfortable living at every turn, and furniture is available for purchase, making this a truly turnkey investment opportunity. The heart of

  

  Kenneth Sabino

  Baird & Warner

  2835 W Wellington Ave Unit 2, Chicago, IL 60618
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  /36

  $365,000

  Pending

  • 6 Beds
  • 3 Baths

  7807 S Evans Ave, Chicago, IL 60619

  Don't miss this beautifully renovated two-unit property offering modern finishes, spacious floor plans, and excellent income potential. The first-floor duplex-down unit features 4 spacious bedrooms and 2 full bathrooms, creating the perfect layout for a large family or premium rental. This stunning unit boasts granite countertops, stainless steel appliances, hardwood flooring throughout the main

  

  Tammy Jackson

  KM Realty Group, LLC

  7807 S Evans Ave, Chicago, IL 60619
• 

  /2

  $124,999

  • 4 Beds
  • 2 Baths

  7327 S Kimbark Ave, Chicago, IL 60619

  Great investment opportunity with strong upside potential! This frame two-flat features two units, each offering 2 bedrooms and 1 bathroom, providing solid rental income possibilities. Both units are currently occupied with month-to-month tenants, making this an ideal option for investors looking for immediate cash flow. While the property does require repairs, it presents a fantastic chance to

  

  Conrad Carpenter

  City & Suburbs Realty, Inc.

  7327 S Kimbark Ave, Chicago, IL 60619
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  /11

  $585,900

  • 9 Beds
  • 6 Baths

  8106 S Langley Ave, Chicago, IL 60619

  THIS BEAUTIFUL THREE-UNIT BRICK BUILDING PRESENTS A RARE INVESTMENT OPPORTUNITY IN THE HIGHLY SOUGHT-AFTER CHATHAM COMMUNITY. CURRENTLY, TWO UNITS ARE OCCUPIED WITH LEASES. THE BUILDING BOASTS THREE EXPANSIVE UNITS, EACH FEATURING THREE BEDROOMS AND TWO BATHROOMS. EACH UNIT INCLUDES STAINLESS KITCHEN APPLIANCES AND WASHER-DRYERS. THE GARDEN UNIT IS EQUALLY IMPRESSIVE, OFFERING THREE SPACIOUS

  

  Robin Saka

  Stages Real Estate LLC

  8106 S Langley Ave, Chicago, IL 60619
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  /13

  $185,000

  Pending

  • 1 Bed
  • 1 Bath

  1348 W Estes Ave Unit 1S, Chicago, IL 60626

  PERFECT FOR HOMEOWNERS OR INVESTORS! Freshly painted throughout with just-restained hardwood floors, this 1 bed, 1 bath condo shines bright with natural light and an open layout. Cozy up by the gas fireplace in the separate living room, and enjoy the dining room's elegant crown molding and tray ceiling, a beautiful spot for entertaining off the kitchen. All stainless appliances complete the

  

  Mark Miles

  Spot Real Estate

  1348 W Estes Ave Unit 1S, Chicago, IL 60626
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  /7

  $240,000

  • 3 Beds
  • 2 Baths

  9211 S Clyde Ave, Chicago, IL 60617

  Excellent opportunity to own a solid two unit building in Calumet Heights with tremendous upside for both investors and owner occupants looking to house hack. The first floor features a one bedroom apartment, while the second floor offers a two bedroom layout, each with separate utilities. The full unfinished basement presents the potential to duplex with the first floor, creating additional

  

  Omar Sanchez

  Habloft LLC

  9211 S Clyde Ave, Chicago, IL 60617
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  /38

  $71,250

  Pending

  • 4 Beds
  • 2 Baths

  5538 S Perry Ave, Chicago, IL 60621

  Step on up...don't be shy! This frame 2-unit is looking for its next owner, and thanks to a recent price improvement, the invitation just got a lot more attractive. Whether you're searching for a property with potential, a place to make your own, or an opportunity to add value through thoughtful updates, this could be the one that earns a spot at the top of your list. Featuring 2 bedrooms and 1

  

  Tamika Marks

  Trademarks & Associates

  5538 S Perry Ave, Chicago, IL 60621
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  /25

  $900,000

  $98K PRICE DROP Pending

  • 6,381 Sq Ft

  6044 N Mozart St, Chicago, IL 60659

  Exceptional Investment Opportunity - Legal 5-Unit Building on an Extra-Wide Lot! Don't miss this rare opportunity to own a legal 5-unit apartment building situated on an oversized 66' x 124' lot in the highly desirable West Ridge neighborhood, just steps from Mather Park and Mather High School. All five apartments are located above grade, providing bright and comfortable living spaces. The

  

  Ryan Luu

  Real People Realty

  6044 N Mozart St, Chicago, IL 60659
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  /15

  $350,000

  $25K PRICE DROP

  • 9 Beds
  • 3 Baths

  7927 S Langley Ave, Chicago, IL 60619

  Exceptional investment opportunity at 7927 S Langley! This maintained multi-unit building features three spacious units, including one oversized 4-bedroom unit and two generous 3-bedroom units-ideal for maximizing rental income or owner-occupant living. Each unit offers ample living space, well-proportioned bedrooms, and functional layouts designed for comfort and convenience. Additionally, each

  

  Tammy Jackson

  KM Realty Group, LLC

  7927 S Langley Ave, Chicago, IL 60619
• 

  /2

  $489,000

  $11K PRICE DROP

  • 4 Beds
  • 2 Baths

  1711 N Austin Ave, Chicago, IL 60639

  - 2-Flat Building in Austin - Perfect for Investors or Owner-Occupants! An excellent investment opportunity awaits in the Austin neighborhood! This property features a spacious 2-flat building, both units are currently occupied. Each unit offers plenty of natural light and spacious layouts. Rental Income $1,600 + $1,600 + $1,450. The full basement provides ample storage or the option for

  

  Bill Eliopoulos

  Cosmos Realty Investors, Inc.

  1711 N Austin Ave, Chicago, IL 60639
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  /9

  $179,900

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths

  11317 S Edbrooke Ave, Chicago, IL 60628

  Excellent opportunity for investors or owner-occupants! This investor-friendly 2-flat duplex offers the perfect chance to live in one unit while generating income from the other, or maximize cash flow by renting both units. The property is ready for your creative vision with minor cosmetic updates and presents immediate income-producing potential. Conveniently located near parks, schools,

  

  Keynu Chambers-McLoyd

  Coldwell Banker Realty

  11317 S Edbrooke Ave, Chicago, IL 60628
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  /35

  $175,000

  Pending

  • 5 Beds
  • 2 Baths

  7930 S Luella Ave, Chicago, IL 60617

  SHORTSALE Opportunity. Not finding what you are looking for in a multi unit? Bring your creative ideas for this diamond in the rough. Building does need work which is reflected in the list price. This Multiunit features enclosed front and back porches, tall ceilings, spacious rooms and floor plan. Great Investment Opportunity For Owner Occupant with the potential to live rent free Or Investor

  

  O'Neia Washington

  O W Auction Group LLC

  7930 S Luella Ave, Chicago, IL 60617
• 

  

  /11

  $227,999

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  1451 E 55th St Unit 1030N, Chicago, IL 60615

  This top-floor corner unit features 3 bedrooms and 2 bathrooms, and has been recently renovated. It is fully occupied under a stable two-year lease, making it a strong income-generating asset from day one. The unit's unique layout, partial lake views, and prime location make it an excellent opportunity for investors, especially those targeting University of Chicago student housing demand. A

  

  Safwan Patel

  YOUMU VENTURES LLC

  1451 E 55th St Unit 1030N, Chicago, IL 60615
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  /32

  $674,999

  • 9 Beds
  • 3 Baths

  4918 N Monticello Ave, Chicago, IL 60625

  This brick multi-unit building in Albany Park is a rare house-hacker and investor opportunity, with 3 spacious 3-bedroom units, a fully finished lower level, and recent big-ticket upgrades already done. These large 3 bedroom units, each with a primary bedroom, formal dining, sunlit living room, and a bright sun room. Market rent runs approximately $2,300 to $2,600 per unit. Expansive finished

  

  Tina Hollins

  Coldwell Banker Realty

  4918 N Monticello Ave, Chicago, IL 60625
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  /10

  $219,999

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  3506 S State St Unit 312, Chicago, IL 60609

  Beautifully maintained 2-bedroom, 1-bath corner unit in an unbeatable location! This bright and airy home is filled with natural light and features an open layout, spacious living area, private balcony off the living room, and convenient in-unit washer and dryer. Ideally located directly across from Illinois Institute of Technology (IIT) and just minutes from public transportation, including CTA

  

  Safwan Patel

  YOUMU VENTURES LLC

  3506 S State St Unit 312, Chicago, IL 60609
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  /34

  $299,900

  • 6 Beds
  • 2 Baths

  1433 S Keeler Ave, Chicago, IL 60623

  Incredible opportunity to own a solid brick 2-unit building at 1433 S Keeler in Chicago. This income-producing property features two spacious units, including a desirable duplex-up second unit that offers added living space, flexibility and the possibility of adding another bathroom. The building has been updated with clean, modern finishes including refreshed flooring, neutral paint tones, and

  

  Chris Weichselbaum

  Fulton Grace Realty

  1433 S Keeler Ave, Chicago, IL 60623
• 

  

  /30

  $289,999

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

  6500 S Minerva Ave Unit 3N, Chicago, IL 60637

  Welcome to 6500 S. Minerva Avenue, Unit 3N, a spacious 2-bedroom, 2-bathroom condo in Chicago's Woodlawn neighborhood near the University of Chicago, Hyde Park, Jackson Park, Lake Michigan, and the Obama Presidential Center. A deeded parking space, in-unit laundry, private balcony, hardwood flooring, low monthly assessments, and no rental restrictions add exceptional flexibility and value. The

  

  Tina Hollins

  Coldwell Banker Realty

  6500 S Minerva Ave Unit 3N, Chicago, IL 60637
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  /7

  $99,900

  Pending

  • Land
  • 3,484 Sq Ft
  • $1,248,750 per Acre

  3808 S Wabash Ave, Chicago, IL 60653

  Exceptional Bronzeville development opportunity on an extra-long 25 x 147 vacant lot currently zoned C1-3. Offering flexibility and strong potential on a predominantly residential block surrounded by neighboring single-family homes and new construction. Ideal opportunity for builders, developers, or buyers looking to explore residential development possibilities in one of Chicago's rapidly

  

  Kimberly Martorano

  @properties Christie's International Real Estate

  3808 S Wabash Ave, Chicago, IL 60653
• 

  

  /38

  $389,999

  • 5 Beds
  • 2 Baths

  712 W Marquette Rd, Chicago, IL 60621

  Discover an exceptional investment or owner-occupant opportunity at 712 W Marquette Road. This classic brick two-unit property offers flexible living arrangements for an extended household, guests, or tenants, along with the potential to generate additional monthly income. The seller has thoughtfully updated both units with new flooring and designer lighting fixtures throughout. Each fully

  

  David Schatz

  Compass

  712 W Marquette Rd, Chicago, IL 60621
• 

  

  /38

  $384,999

  Pending

  • 5 Beds
  • 2 Baths

  6018 S Sangamon St, Chicago, IL 60621

  Discover 6018 S Sangamon Street-a stunningly updated greystone 2-flat, ideal for both investors and owner-occupants. Each unit boasts over 1,300 sq. ft. of living space, brand-new mechanicals and appliances and modern finishes throughout. Unit 1 offers 2 bedrooms and 1 bathroom, while Unit 2 provides 3 bedrooms and 1 bathroom. Enjoy LVP flooring and sleek kitchens featuring quartz countertops,

  

  David Schatz

  Compass

  6018 S Sangamon St, Chicago, IL 60621
• 

  

  /23

  $930,000

  Pending

  • 9 Beds
  • 6 Baths

  6508 S Ingleside Ave, Chicago, IL 60637

  Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building

  

  Richard Lomax

  Fulton Grace Realty

  6508 S Ingleside Ave, Chicago, IL 60637
• 

  

  /61

  $450,000

  • 9 Beds
  • 4 Baths

  8019 S Rhodes Ave, Chicago, IL 60619

  Situated in the heart of Chatham, this exceptionally well-kept 3-flat is a true income-producing opportunity that's ready to go from day one. The property features three generous units, each approximately 1,200 square feet, showcasing soaring 9-foot ceilings, hardwood flooring, and thoughtfully designed layouts with separate living and dining areas. Spacious kitchens offer abundant cabinetry and

  

  Rafay Qamar

  Real Broker LLC

  8019 S Rhodes Ave, Chicago, IL 60619
• 

  

  /16

  $260,000

  • 11 Beds
  • 7 Baths

  1837 S Komensky Ave, Chicago, IL 60623

  Great opportunity for investors, rehabbers, and developers! This legal 3-unit building with a partially finished basement is located in the desirable Lawndale neighborhood of Chicago and offers tremendous value-add potential.Each of the three spacious units features a large living room, separate formal dining room, separate kitchen, three generously sized bedrooms, 1 full bathroom, and 1 half

  

  Ryan Luu

  Real People Realty

  1837 S Komensky Ave, Chicago, IL 60623

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