Investment - Homes for Sale in Chicago, IL

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  /7

  $775,000

  • 8 Beds
  • 5 Baths

  5955 W Superior St, Chicago, IL 60644

  Superior New Construction on Superior Street! Exceptional custom-built 3-unit investment property situated on an oversized lot with over 4,800 square feet of land, just moments from Oak Park. This newer construction building offers an outstanding opportunity for both investors and owner-occupants alike. Each spacious unit features 3 bedrooms, 2 full bathrooms, soaring 10-foot ceilings, generous

  Daniela Recillas RE/MAX ELEVATED LLC

  5955 W Superior St, Chicago, IL 60644
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  /39

  $450,000

  Pending

  • 9 Beds
  • 4 Baths

  9018 S Houston Ave, Chicago, IL 60617

  Legal 4-unit property in South Chicago featuring a rare, self-contained ADU - and an outstanding investment opportunity! The main building offers a 3-bedroom/1-bath on the first floor and two 2-bedroom/1-bath units on the upper floors, each with a full living room, dining room, kitchen, and pantry. The 2nd floor unit was fully rehabbed in 2025. All units are separately metered, keeping operating

  Leo Sanchez Realty of America, LLC

  9018 S Houston Ave, Chicago, IL 60617
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  /16

  $280,000

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  10753 S Hale Ave, Chicago, IL 60643

  Attention Investors and Rehabbers Exceptional Investment opportunity on a quiet, tree-lined residential block located in the Beverly Park area. This solid built brick home features 3 bedrooms, and 1 full bathroom, and full size attic that can be converted into an additional bedroom. Property features Central air and hardwood floors. Approx. 1,250 square feet of living space, sitting on a massive

  Porsha Cochran Century 21 Universal

  10753 S Hale Ave, Chicago, IL 60643
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  /9

  $130,000

  • 4 Beds
  • 2 Baths

  1710 W Waseca Place, Chicago, IL 60643

  Stop paying rent and let a tenant subsidize your mortgage. This solid 2-unit Morgan Park property offers the ideal house-hacking setup: live in one unit while collecting steady rental income from the second. Both apartments showcase original hardwood floors, sun-drenched rooms, classic radiator heat, and private access to the multi-level back deck. Nestled in a quiet, tree-lined neighborhood with

  Elijah Reese Serene Realty, Inc.

  1710 W Waseca Place, Chicago, IL 60643
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  /41

  $610,000

  $40K PRICE DROP

  • 7 Beds
  • 4 Baths

  441 E 42nd St, Chicago, IL 60653

  Nestled in the heart of historic Bronzeville, 441 E. 42nd Street presents a rare chance to own a classic Chicago greystone in one of the city's most dynamic and culturally rich neighborhoods. Spanning more than 4,000 square feet above grade, this updated three-unit building offers remarkable versatility for investors and owner-occupants alike. Updated in 2021, the property lends itself to a

  Michala Hood Charles Rutenberg Realty of IL

  441 E 42nd St, Chicago, IL 60653
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  /2

  $30,000

  • Land
  • 0 Sq Ft

  1455 S Kilbourn Ave, Chicago, IL 60623

  ATTENTION INVESTORS, DEVELOPERS & BUILDERS! Excellent opportunity to acquire vacant land at 1455 S. Kilbourn Avenue and bring your next residential development project to life. Consider the possibilities of developing a multi-unit residential property designed to create multiple income streams from one parcel. Multi-unit development can be an attractive long-term investment strategy because it

  Terina Fountain Coldwell Banker Realty

  1455 S Kilbourn Ave, Chicago, IL 60623
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  /20

  $319,000

  Pending

  • 11 Beds
  • 3 Baths

  8942 S Baltimore Ave, Chicago, IL 60617

  Legal 3-Unit Investment Opportunity! Great location just minutes from shopping, local dining, and the lakefront. Renovated in 2023, this income-producing property offers excellent potential for an investor or owner-occupant. Major updates completed in 2023 include plumbing, electrical, mechanicals, and hot water tanks. Each unit is equipped for stackable laundry and features central air. Property

  Sheena Manning Realty of America, LLC

  8942 S Baltimore Ave, Chicago, IL 60617
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  /14

  $99,750

  Pending

  • 5 Beds
  • 2 Baths
  • 920 Sq Ft

  5242 S Sangamon St, Chicago, IL 60609

  Spacious 4-bedroom, 2-bathroom, two story frame home located in the New City neighborhood. This property features a full finished basement and a 2-car garage, offering plenty of space and functionality. It is conveniently situated near schools, shopping, and public transportation. Room sizes and counts are estimates. No surveys nor disclosures will be provided. Great investment opportunity--add

  Michael Olszewski Area Wide Realty

  5242 S Sangamon St, Chicago, IL 60609
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  /15

  $699,000

  • 8 Beds
  • 6 Baths

  1505 S Spaulding Ave, Chicago, IL 60623

  Fully renovated three-unit Greystone in North Lawndale! Excellent opportunity for owner occupant or house hacking/investment. Property offers new mechanical, electrical, and plumbing system, new roof, Modern kitchens with white shaker cabinets and quartz countertops, Updated bathrooms and Separate utilities for each unit. First floor offers 2 bedrooms and 2 bathrooms and second and third floor

  Eboni Mills EXIT Strategy Realty

  1505 S Spaulding Ave, Chicago, IL 60623
• 

  

  /21

  $99,000

  Pending

  • 4 Beds
  • 2 Baths

  11612 S Lafayette Ave, Chicago, IL 60628

  Excellent investment opportunity! This 2-flat sits on a large lot and offers unlimited potential for investors, rehabbers, or owner-occupants looking to build equity. Property is being sold AS-IS. Conveniently located just minutes from the Dan Ryan Expressway (I-94) and I-57, providing easy access for commuters. Spacious lot offers additional possibilities. Don't miss this chance to add value to

  Jaime Birks Realty of America

  11612 S Lafayette Ave, Chicago, IL 60628
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  /26

  $599,000

  • 12 Beds
  • 4 Baths

  1301 S Christiana Ave, Chicago, IL 60623

  LARGE updated legal four in rapidly appreciating North Lawndale. 1301 S Christiana boasts updated units with modern efficiencies like in-unit washers and dryers, individual furnaces and central air in EVERY UNIT, and updated kitchens with beautiful granite countertops. The property was built big extending to the sidewalk to create above standard units with plenty of sunlight since it is on the

  Sarita Scherpereel Kale Realty

  1301 S Christiana Ave, Chicago, IL 60623
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  /36

  $689,900

  New Construction Pending

  • 5 Beds
  • 4 Baths

  6641 S Evans Ave, Chicago, IL 60637

  Introducing the second and final two-unit residence at Deux on Evans. With the first residence already under contract, this is the remaining opportunity to own within this distinctive new construction development in West Woodlawn. Qualified buyers automatically receive a $20,000 grant that may be applied toward eligible closing costs and qualifying funds needed to purchase the home. Qualified

  Jennifer Bell Fulton Grace Realty

  6641 S Evans Ave, Chicago, IL 60637
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  /13

  $95,000

  $25K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft

  8112 S Escanaba Ave, Chicago, IL 60617

  Smart Investment or Ideal Starter Home! Currently Rented and Cash flowing nicely! Welcome to this delightful 4-bedroom, 2 full bath 1.5-story single-family home offering charm, comfort, and opportunity. Nestled in a quiet neighborhood. Whether you're looking to move in and make it your own or capitalize on rental income, this home checks all the boxes. With strong rental potential and a location

  Damaris Santiago Manage Chicago, Inc.

  8112 S Escanaba Ave, Chicago, IL 60617
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  /10

  $279,900

  $5K PRICE DROP

  • 10 Beds
  • 3 Baths

  7749 S Muskegon Ave Unit MRD12521789, Chicago, IL 60649

  TIME to make some MONEY on your INVESTMENT - This 3-UNIT Building is already a MONEY MAKER - Very Clean - Well Taken Care of - SECURITY Lights surround the entire exterior - Newer Wooden Porches (2017) - Newer Windows (3rd Floor) - Newer Furnace (1st Floor) - New Patio (2025) - Newer Hot Water Tanks - Very Close to Shopping - Public Transportation -

  Bud Steele Steele Realty Group, Inc.

  7749 S Muskegon Ave Unit MRD12521789, Chicago, IL 60649
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  /23

  $499,900

  • 8 Beds
  • 3 Baths

  4051 W Monroe St, Chicago, IL 60624

  **Solid investment opportunity in West Garfield Park!** This 2-flat with a finished garden-level unit offers three occupied units and strong income potential. The first-floor unit features 3 bedrooms and 1 bath, was renovated in 2024, and currently rents for $1,200/month MTM, due on the 15th. The second-floor 3-bedroom, 1-bath unit rents for $950/month MTM, due on the 1st. The newly renovated

  Gina Purdy Baird & Warner

  4051 W Monroe St, Chicago, IL 60624
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  /32

  $119,900

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  4800 S Chicago Beach Dr Unit 1503S, Chicago, IL 60615

  Luxury living awaits at The Newport, one of Hyde Park's premier full-amenity buildings. This spacious 1-bedroom, 1-bathroom condo offers an incredible opportunity to add your personal touches while enjoying exceptional building amenities and an unbeatable location. Step inside to discover a bright, expansive living space featuring a dramatic wall of windows that fills the home with natural light.

  Kelly Klaff RE/MAX 10

  4800 S Chicago Beach Dr Unit 1503S, Chicago, IL 60615
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  /3

  $175,000

  • 4 Beds
  • 2 Baths
  • 1,667 Sq Ft

  320 W 111th Place, Chicago, IL 60628

  Excellent Investment Opportunity or Owner-Occupant! Welcome to 320 W. 111th Place, a well-maintained two-unit frame building in Chicago's Roseland neighborhood. Each unit features 2 bedrooms and 1 full bathroom with functional floor plans and excellent potential for customization. Major exterior improvements have already been completed, including a newer roof, updated siding, and an updated

  Nickolas Katsoulos Property Outlet Group LLC

  320 W 111th Place, Chicago, IL 60628
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  /2

  $9,999

  • Land
  • 0 Sq Ft

  7318 S Paulina St, Chicago, IL 60636

  Development Opportunity in West Englewood! This location is ideal for those seeking a strategic investment in a rapidly developing area. A mix of modern and newly renovated homes, with continued growth in the area. The Chicago neighborhood is seeing increasing development and revitalization, making this an excellent opportunity to invest in an area with great potential for future appreciation.

  Chanee Roby Coldwell Banker Real Estate Group

  7318 S Paulina St, Chicago, IL 60636
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  /8

  $140,000

  • 5 Beds
  • 3 Baths
  • 1,743 Sq Ft

  6037 S Racine Ave, Chicago, IL 60636

  Good opportunity to own this single family home with 3 levels of living space. Great for owner occupy or investment. 1st and lower level has 2 bedrooms , kitchen , bath and living room. Attic offers 1 bedrooms , 1 bath and living area .

  Taurino Morales eXp Realty

  6037 S Racine Ave, Chicago, IL 60636
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  /3

  $630,000

  Open Sat 1PM - 3PM $40K PRICE DROP

  • 14 Beds
  • 6 Baths

  1513 E 93rd St, Chicago, IL 60619

  Great for investors or owner-occupants who want built-in rental income.Turnkey and smoke-free 4-unit investment in Chicago! Fully rehabbed in 2022 with two 4BR/2BA and two 3BR/1BA units, all with private W/D, HVAC, and stainless appliances. New electrical, plumbing, windows & floors throughout. Ample space and storage in the basement; potential duplex down for the 1st-floor units. Minutes to

  Donna White AXEN Realty LLC

  1513 E 93rd St, Chicago, IL 60619
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  /2

  $459,000

  • Studio
  • 1 Bath
  • 918 Sq Ft

  401 N Wabash Ave Unit 2140, Chicago, IL 60611

  Live at the pinnacle of Chicago luxury. This meticulously furnished residence in one of the city's most iconic five-star buildings offers a refined turnkey lifestyle. The chef's kitchen is a study in form and function, featuring sleek Snaidero cabinetry and a full suite of Miele and Sub-Zero stainless steel appliances. As an owner, you'll enjoy the privileges of Trump Hotel's five-star

  James Qiu Kale Realty

  401 N Wabash Ave Unit 2140, Chicago, IL 60611
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  /7

  $475,000

  $25K PRICE DROP

  • 9 Beds
  • 3 Baths

  9133 S Essex Ave, Chicago, IL 60617

  Fully occupied 3-unit investment property offering strong rental potential in Chicago. Rehabbed in 2020, this well-maintained building features three spacious units, each offering 3 bedrooms and 1 bathroom. Interior highlights include hardwood flooring throughout and on-site laundry for tenant convenience. Exterior features include a fenced yard, providing additional outdoor space and privacy.

  Samantha Swaney GC Realty and Development

  9133 S Essex Ave, Chicago, IL 60617
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  /26

  $400,000

  • 2 Beds
  • 1 Bath

  869 N La Salle Dr Unit 2, Chicago, IL 60610

  **Leased through July 31, 2027. $2906 per month** Rare opportunity to own in Chicago's Near North neighborhood at an unbeatable value with exceptionally low monthly assessments. This cozy unit offers a unique blend of city living and a private home feel, facing Moody Bible's park with no obstructing buildings. Perfectly situated near popular Gold Coast, Old Town, and River North landmarks, it's

  Michael Saladino Keller Williams ONEChicago

  869 N La Salle Dr Unit 2, Chicago, IL 60610
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  /16

  $229,900

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft

  88 W Schiller St Unit 1003L, Chicago, IL 60610

  A bright and inviting one-bedroom residence in the heart of Chicago's Gold Coast, perfectly positioned at the corner of Clark and Schiller in Lowell House at Carl Sandburg Village. Set above the neighborhood tree line, this 10th-floor home enjoys an abundance of natural light along with a lovely north-facing outlook over the surrounding canopy and a peek of Lake Michigan to the east. The

  Jill Silverstein Compass

  88 W Schiller St Unit 1003L, Chicago, IL 60610
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  /2

  $165,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths

  7709 S Ada St, Chicago, IL 60620

  Excellent investment opportunity in the Auburn Gresham neighborhood of Chicago! This spacious 2-unit property offers strong potential for investors or rehabbers looking to add value. The building requires renovation, making it ideal for a full rehab project. Conveniently located near schools, parks, shopping, dining, and public transportation. Bring your vision and transform this property into a

  Phyllis Smart Hoff, Realtors

  7709 S Ada St, Chicago, IL 60620
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  /42

  $1,050,000

  6751 S Chappel Ave, Chicago, IL 60649

  Priced to Sell! Prime investment opportunity in the highly desirable South Shore neighborhood of Chicago, just steps from DuSable Lake Shore Drive. This well positioned 20 unit residential building offers strong income potential in a location known for steady rental demand and convenient access to the lakefront, transportation, and neighborhood amenities. The property consists of twenty (20)

  Michael Olszewski Area Wide Realty

  6751 S Chappel Ave, Chicago, IL 60649
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  /11

  $2,250,000

  $165K PRICE DROP

  4150 S Western Ave, Chicago, IL 60609

  BUY IN BULK AND SAVE. SEE CONDO SALES IN THE AREA. HUGE UPSIDE POTENTIAL! SELL OFF ONE BY ONE, CREATE THE HOA AND HAVE RECURRING INCOME! Exceptional investment opportunity in the heart of Bridgeport! This offering consists of 10 residential units located within four side-by-side newer-construction, four-story mixed-use buildings in one of Chicago's most sought-after and rapidly growing

  Jim Mantas The Leading Realtors Corp.

  4150 S Western Ave, Chicago, IL 60609
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  /117

  $1,705,000

  Pending

  4240 S Calumet Ave, Chicago, IL 60653

  7.5 CAP Breathe Rare Air. The sellers of this property portfolio are not just seasoned investors; they are passionate visionary stewards with over 45 years of experience in branded high quality property development and management. Since 2007, they have meticulously curated each asset in the Bronzeville collection, focusing on longevity, quality, and the future potential of every investment. Every

  Karen Biazar North Clybourn Group, Inc.

  4240 S Calumet Ave, Chicago, IL 60653
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  /44

  $275,000

  Pending

  • 7 Beds
  • 3 Baths

  5542 S Paulina St, Chicago, IL 60636

  ***MULTIPLE OFFERS RECEIVED*** Highest and best offers due by Tuesday at 9 am. Unlock the potential of this exceptional income-producing property! This spacious 2-unit building with non-confoming basement unit offers a total of 7 bedrooms and 3 bathrooms, making it an outstanding opportunity for investors or owner-occupants seeking additional rental income. The partially finished basement

  Jean Walker Redfin Corporation

  5542 S Paulina St, Chicago, IL 60636
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  /43

  $989,900

  New Construction

  • 6 Beds
  • 7 Baths

  2849 W Monroe St, Chicago, IL 60612

  **Exceptional New Construction 3-Unit Investment Opportunity!** Don't miss this beautifully newly constructed brick and Hardie siding 3-unit building, designed with modern finishes, spacious layouts, and outstanding income potential. Whether you're an investor looking for a turnkey rental property or an owner-occupant seeking additional rental income, this property is ready for immediate

  Neelam Dwivedi RAJ Realty & Investment Co.

  2849 W Monroe St, Chicago, IL 60612
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  /36

  $510,000

  $10K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 938 Sq Ft

  401 N Wabash Ave Unit 39E, Chicago, IL 60611

  Experience life within one of Chicago's most iconic architectural landmarks. Residence 39E at Trump Tower Chicago offers a sophisticated living experience designed by renowned architect Adrian Smith, whose work has shaped skylines around the world. This pristine 1-bedroom, 1.5-bath residence features soaring 10-foot ceilings and dramatic floor-to-ceiling windows showcasing breathtaking city

  Chezi Rafaeli Coldwell Banker Realty

  401 N Wabash Ave Unit 39E, Chicago, IL 60611
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  /2

  $25,000

  • Land
  • 0 Sq Ft

  7259 S Harvard Ave, Chicago, IL 60621

  Build your dream home on this spacious, 0.5-acre residential lot in the Greater Grand Crossing neighborhood. The land is flat and cleared, making it ready for construction. City water and sewer available at the street. Don't miss out on this prime spot for investment to create the perfect home!

  Rockeya Wilson Berkshire Hathaway HomeServices Chicago

  7259 S Harvard Ave, Chicago, IL 60621
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  /28

  $749,000

  Pending

  • 7 Beds
  • 3 Baths

  3344 N Monticello Ave, Chicago, IL 60618

  Best and final due 9/13 at 10AM. JUMBO BRICK LEGAL 3-FLAT on an EXTRA-WIDE 31' x 126' LOT! An exceptional opportunity for both investors and owner-occupants, this well-maintained three-unit property offers 7 total bedrooms and 3 bathrooms with generously sized interiors throughout. The building features a 1-bedroom/1-bath garden unit and two spacious 3-bedroom/1-bath residences on the first and

  Jill Silverstein Compass

  3344 N Monticello Ave, Chicago, IL 60618
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  /31

  $275,000

  $25K PRICE DROP Pending

  • 10 Beds
  • 3 Baths

  1512 S Sawyer Ave, Chicago, IL 60623

  Investor opportunity! Solid-brick multi-family building featuring 2 oversized residential units, an occupied income-producing garden apartment, detached 2-car garage, separate utilities, and a full basement with exterior access. Offering significant value-add potential, this property is ideal for investors seeking a rehab project, BRRRR strategy, long-term hold, or owner-occupants looking to

  Sidney Martin Century 21 S.G.R., Inc.

  1512 S Sawyer Ave, Chicago, IL 60623
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  /18

  $200,000

  • Land
  • 0 Sq Ft

  5100 S Francisco Ave, Chicago, IL 60632

  Exceptional development opportunity featuring a double residential vacant lot at 5100 S Francisco Ave in Chicago! This vacant lot offers an opportunity for builders, developers, and investors to bring their vision to life. With generous frontage to 51st ST, the property is well-suited for residential investment development zoned as RS-3 (subject to zoning and City approvals). Ideally located on

  Miguel Sanchez Ruiz Realty, Inc.

  5100 S Francisco Ave, Chicago, IL 60632
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  /40

  $1,199,999

  • 8 Beds
  • 3 Baths

  1812 W Erie St, Chicago, IL 60622

  FULLY rehabbed approximately two years ago and FULLY occupied, this turn-key 3-unit building sits on one of West Town's BEST blocks, surrounded by new construction and continued development. Each unit was thoughtfully updated with new flooring, appliances, cabinetry, countertops, HVAC systems (3), AC units (3), in-unit washers and dryers (3), dishwashers (2), windows, siding, closet organizers,

  Melanie Giglio-Vakos Compass

  1812 W Erie St, Chicago, IL 60622
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  /10

  $349,999

  • 9 Beds
  • 4 Baths

  8329 S Buffalo Ave, Chicago, IL 60617

  Excellent 4-unit investment opportunity with immediate income and value-add potential! This well-maintained multifamily property features two 3-bedroom units and two 2-bedroom units, providing a desirable mix of rental options. Three units were renovated in 2021, while the remaining unit offers an opportunity for renovation and potential rent growth. Each unit has its own furnace, and three units

  Yomaira Roman Herrera RE/MAX LOYALTY

  8329 S Buffalo Ave, Chicago, IL 60617
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  /15

  $95,000

  Pending

  • 5 Beds
  • 3 Baths

  6554 S Stewart Ave, Chicago, IL 60621

  Bring your vision to life with this substantial investment opportunity, fully demoed to the studs and ready for redevelopment. Plans were previously submitted to the City and are available upon request. A newer roof is in place. The property offers an impressive amount of space and income potential, with 2-bedroom, 1-bath layouts on both the first and second floors, plus a 1-bedroom attic

  Antonio Rubio eXp Realty

  6554 S Stewart Ave, Chicago, IL 60621
• 

  

  /27

  $239,000

  $10K PRICE DROP Pending

  • 5 Beds
  • 3 Baths

  10305 S Avenue J, Chicago, IL 60617

  Early American Investment Property. Three Units Building. 2-2 bedrooms units and 1-1 bedroom unit. Separate utilities for each apartment, some freshly painted rooms, some need work getting ready for new owner final touches. Sold as is! Full basement, newer windows, spacious back yard and 2 car garages with space for 3 cars. Call for a free pass to see!

  Pastora Sanchez Central Realty-Kralj & Sanchez

  10305 S Avenue J, Chicago, IL 60617
• 

  

  /5

  $734,900

  $10K PRICE DROP

  • 5 Beds
  • 3 Baths

  5600 N Mango Ave, Chicago, IL 60646

  Nice corner well maintained legal 2 flat with additional in law apartment in basement. All are spacious apartments including basement. 1st and 2nd floor units have formal dining rooms. All separate utilities. New furnace and AC units on each apartment. 1ST and 2nd floor have new SS appliances. Coin-operated laundry located in the basement. Good rents make this a great investment.

  Tony Garcia Terra Nova Realty Group Corp

  5600 N Mango Ave, Chicago, IL 60646

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