Investment - Homes for Sale in Chicago, IL

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  /2

  $10,000

  $50K PRICE DROP

  • 5 Beds
  • 2 Baths

  5802 S May St, Chicago, IL 60621

  Come and view this excellent investment and renovation project. This 2 flat offers a spacious 2br 1bth unit and a 3br 1bth unit. Full basement. Property Sold AS/WHERE-IS. Buyer responsible for all liens, taxes, judgments, closing costs. Seller does not know the amount, so do your due diligence. No tax prorations.

  Edrick Salomon Select a Fee RE System

  5802 S May St, Chicago, IL 60621
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  /17

  $315,000

  Pending

  • 6 Beds
  • 2 Baths

  8125 S Evans Ave, Chicago, IL 60619

  Welcome to a versatile and income-generating multi-family mult-unit situated in a cozy, well-maintained neighborhood within the Chatham community. Whether you're seeking a live-in owner opportunity or a landlord investment, this residence is poised for rental income or owner-occupancy with solid upside potential. Don't miss your chance to own a piece of historic character in a vibrant South Side

  Xiomara Maldonado North Clybourn Group, Inc.

  8125 S Evans Ave, Chicago, IL 60619
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  /36

  $340,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft

  728 W Jackson Blvd Unit 724, Chicago, IL 60661

  Experience elevated loft living at Haberdasher Square Lofts, one of the West Loop's most iconic full-amenity buildings, where soaring 12-foot ceilings, exposed timber beams, floor-to-ceiling windows, and abundant natural light create a truly spectacular living space. This impeccably updated residence is completely move-in ready, featuring a designer kitchen, renovated bath, beautifully

  Anne Chantos Coldwell Banker Realty

  728 W Jackson Blvd Unit 724, Chicago, IL 60661
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  /76

  $1,800,000

  $200K PRICE DROP

  • 5,500 Sq Ft

  843 W Roscoe St, Chicago, IL 60657

  Multiple Offers Received. Highest Best due by 9-21-2026 at 1:00PM. Estate Sale in East Lakeview - First time on the market in 57 years! Well maintained, iconic Chicago style BRICK BUILDING plus COACH HOUSE, totaling FIVE UNITS & located on tree-lined Roscoe Street! Front building has THREE units (all 2 bed/1 bath) and a full, unfinished basement. Coach House w/TWO additional units (1 bed/1 bath &

  Brian Brak Brak Realty Inc.

  843 W Roscoe St, Chicago, IL 60657
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  /33

  $599,999

  Pending

  • 7 Beds
  • 3 Baths

  1747 N Luna Ave, Chicago, IL 60639

  Welcome to this beautifully renovated 2-unit building in the sought-after Austin neighborhood! Offering a total of 7 bedrooms, 3 bathrooms, a fully finished basement, and central air conditioning, this turnkey property is an exceptional opportunity for both owner-occupants and investors. The first-floor unit features a bright and spacious living room, a separate dining room, and a stunning newly

  Paula Tito Realty of America, LLC

  1747 N Luna Ave, Chicago, IL 60639
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  /17

  $2,150,000

  • 6 Beds
  • 6 Baths

  1420 W Fulton St, Chicago, IL 60607

  Beautiful historic brick 3 unit In Fulton Market's HOT West Loop. This rare three-unit luxury rental structure is exactly in the path of new developments. No money was spared and fully rehabilitated in 2016. Three brand-new, identical apartments that have been completely remodeled with premium finishes and appliances. Sleek two-bedroom, two-bathroom apartments with the same layout. Kohler kitchen

  Rick Panlilio RE/MAX Premier Luxury Collection

  1420 W Fulton St, Chicago, IL 60607
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  /52

  $675,000

  Pending

  • 8 Beds
  • 4 Baths

  5723 N Artesian Ave, Chicago, IL 60659

  Desirable Arcadia Terrace! Incredible investment opportunity with this all-brick 2-flat, including a non-conforming basement space, storage, laundry room and a 2-car garage. Units 1 & 2 feature hardwood flooring, 3-bedrooms / 1 bath. Unit 2 includes a FULLY updated kitchen & bath. The 2-Flat features recently updated electrical and tuck-pointing ( 5yrs). Age of roof is unknown and building is

  Alley Ballard @properties Christie's International Real Estate

  5723 N Artesian Ave, Chicago, IL 60659
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  /16

  $285,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths

  10538 S Vincennes Ave, Chicago, IL 60643

  Rare opportunity to own a spacious two-unit building in the highly sought-after Beverly neighborhood with the additional lot to the north of the property included! Whether you're an investor looking to add to your portfolio or a homeowner interested in house hacking, this property offers incredible potential. Each unit features 2 bedrooms, 1 full bath, a large living room, separate dining room,

  Carolyn Barnes Real People Realty

  10538 S Vincennes Ave, Chicago, IL 60643
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  /20

  $300,000

  $20K PRICE DROP Pending

  • 5 Beds
  • 3 Baths

  3017 E 83rd St, Chicago, IL 60617

  Excellent investment opportunity in Chicago! This well-maintained two-unit property offers incredible versatility for investors or owner-occupants looking to generate rental income. The main building features two spacious units with bright living areas, updated flooring, generous room sizes, and functional layouts designed for comfortable living. A standout feature of this property is the

  Dione Branch eXp Realty

  3017 E 83rd St, Chicago, IL 60617
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  /42

  $1,050,000

  Pending

  • 8 Beds
  • 4 Baths

  3245 W Division St, Chicago, IL 60651

  Ideally located just steps from Humboldt Park, this rare income property features an oversized all-brick building on an extra-wide and extra-deep 30 x 130 lot in one of Chicago's most dynamic neighborhoods, where rents are surging and investment momentum continues to accelerate. This fully leased investment property generates $107K in annual rent delivering strong, reliable cash flow from day

  Greg Nagel Ask Nagel

  3245 W Division St, Chicago, IL 60651
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  /4

  $157,900

  • Land
  • 0 Sq Ft

  4950 W Diversey Ave, Chicago, IL 60639

  Great opportunity for builders and investors!!!! Vacant city lot with a newer three-car garage already in place. Ready for your next investment project or hold for future appreciation .Buyer to verify zoning and building requirements

  Marek Predki Avondale Realty LLC

  4950 W Diversey Ave, Chicago, IL 60639
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  /2

  $40,000

  • Land
  • 0 Sq Ft

  5647 S Peoria St, Chicago, IL 60621

  Prime South Side Development Opportunity: Unlock the potential at 5647 S. Peoria. This 4,500 sq ft vacant lot offers a rare opportunity for builders, developers, and forward-thinking investors ready to capitalize on Chicago's ongoing growth and revitalization. Positioned in an established South Side corridor, this parcel provides the flexibility to bring new construction to life-whether you're

  Elijah Reese Serene Realty, Inc.

  5647 S Peoria St, Chicago, IL 60621
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  /14

  $349,999

  $145K PRICE DROP

  • 9 Beds
  • 3 Baths

  3018 W Flournoy St, Chicago, IL 60612

  Large brick 3-unit investment opportunity with major upside potential. Property previously underwent extensive renovation work including updated kitchens, bathrooms, refinished hardwood floors, recessed lighting, newer HVAC systems, updated mechanicals, newer appliances, and exterior improvements. Spacious layouts with strong rental and value-add potential. Interior photos reflect prior

  Misael Chacon Beycome Brokerage Realty LLC

  3018 W Flournoy St, Chicago, IL 60612
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  /26

  $399,900

  $20K PRICE DROP Pending

  • 8 Beds
  • 3 Baths

  5029 S Racine Ave, Chicago, IL 60609

  Fantastic opportunity to build equity and expand your portfolio with this spacious multi-unit property in the Back of the Yards neighborhood! This property features 3 units: The first-floor unit boasts high ceilings, 4 generously sized bedrooms, a full bath, an eat-in kitchen, a spacious living room and a month-to-month tenant. The second-floor front unit includes 2 bedrooms, a full bath, a

  Jose Leon RE/MAX Partners

  5029 S Racine Ave, Chicago, IL 60609
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  /28

  $130,000

  $5K PRICE DROP Pending

  • 8 Beds
  • 5 Baths

  8711 S Exchange Ave, Chicago, IL 60617

  Exceptional Investment Opportunity in this 4-Unit building in South Chicago neighborhood ! This high-potential property presents a rare opportunity for savvy investors. Additional in-law arrangement garden unit plus large and high attic . The building spans approximately 3,050 square feet and features 10 bedrooms, 5 bathrooms and a detached 2-car garage. Prime location close to parks, stores, and

  Grazyna Przybysz Chicago Area Realty Inc

  8711 S Exchange Ave, Chicago, IL 60617
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  /12

  $379,900

  Pending

  • 4 Beds
  • 3 Baths

  1842 N Keeler Ave, Chicago, IL 60639

  INVESTIORS SPECIAL!!! Don't Miss This Exceptional Investment Opportunity in Hermosa! IDEAL APPORTUNITY FOR FLIPPERS OR HANDY BUYERS. Flip it or keep it!!! This multi-unit building is a true gem, 2 units plus garden unit (3 units total). Featuring two spacious 2-bedroom, 1-bathroom apartments. Whether you're a seasoned investor or a savvy buyer ready to live and earn, this is a must-see property

  Renata Pieczka xr realty

  1842 N Keeler Ave, Chicago, IL 60639
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  /2

  $239,900

  Pending

  • 2 Beds
  • 1 Bath

  1003 N Francisco Ave, Chicago, IL 60622

  Great investment opportunity! This property offers a great opportunity to bring your vision to life. In need of renovation, this home is ideal for those looking to add value and customize to their liking. Spacious layout with strong potential for a full transformation. Being sold as-is.

  JC Gonzalez eXp Realty

  1003 N Francisco Ave, Chicago, IL 60622
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  /5

  $110,000

  $67K PRICE DROP Pending

  • 4 Beds
  • 3 Baths

  5350 S Winchester Ave, Chicago, IL 60609

  QUIET BLOCK IN UPCOMING NEW CITY NEIGHBORHOOD! Seller is motivated yet comps in area show lots of room to make this *vacant* BRICK 2 flat with 4 beds and 3 bath (yet a very large living room to add a third bedroom in one of the apartments) a basic rental or a splendid work of art at whatever level of creativity you desire! GREAT POSSIBILITIES!!!!. Turn this in to a wonderful investment property

  Dana Jones Century 21 IMPACT

  5350 S Winchester Ave, Chicago, IL 60609
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  /2

  $150,000

  • 5 Beds
  • 3 Baths
  • 1,300 Sq Ft

  1508 S Komensky Ave, Chicago, IL 60623

  Calling all investors, rehabbers, and savvy buyers! Bring your vision and transform this 5-bedroom, 3-bath single-family home into your next successful project. Offering approximately 1,300 square feet of living space, this property has been taken down and framed out, providing a head start for the buyer ready to complete the renovation and bring the home back to life. The existing layout offers

  Aaron Gaines Keller Williams Preferred Realty

  1508 S Komensky Ave, Chicago, IL 60623
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  /19

  $4,600,000

  • 10 Beds
  • 10 Baths

  Unlisted Address

  Incredible Investment & Development Opportunity in the Heart of Old Town! Maximize your portfolio with this rare multi-unit property and double-lot package in one of Chicago's premier, high-demand neighborhoods. This turnkey investment features a beautifully and recently renovated, all-brick 4-flat paired with two adjacent lots, delivering immediate strong cash flow alongside massive future

  Maurice Ortiz Compass

  Unlisted Address
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  /24

  $65,000

  $5K PRICE DROP Pending

  • 5 Beds
  • 3 Baths

  8405 S Baltimore Ave, Chicago, IL 60617

  Solid investment opportunity with strong upside potential. This frame 2-flat includes two spacious 2-bedroom units and an additional 1-bedroom garden unit, offering multiple income streams. The property features individual heating systems for each unit, improving efficiency and tenant appeal. While the building requires rehabilitation, it presents a prime value-add opportunity for investors

  Brenda Molina HomeSmart Connect LLC

  8405 S Baltimore Ave, Chicago, IL 60617
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  /2

  $29,999

  • Land
  • 0 Sq Ft

  7239 S Vincennes Ave, Chicago, IL 60621

  Unlock your development vision with this 2,567 sq ft vacant lot, zoned RS-3 and ideal for a single-family residence or other multi-family residential use (buyer to verify). Whether you're a builder, investor, or future homeowner, this site offers a perfect blank canvas for your next project. Even better - the owner is willing to sell all 12 adjoining lots as a bundle, offering a rare opportunity

  Anthony Khoshabe United Realty and Development

  7239 S Vincennes Ave, Chicago, IL 60621
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  /31

  $895,000

  Pending

  • 6 Beds
  • 3 Baths

  1317 W Elmdale Ave, Chicago, IL 60660

  Rare Magnolia Glen jumbo brick 2-flat on a quiet, one-way, tree lined street in Chicago's best neighborhood! Exceptionally well maintained and filled with original vintage character, including beautiful woodwork, built-ins, stained glass windows, box beam ceilings, hardwood floors, separate living and dining rooms, large pantries, charming front sunrooms, and rear enclosed porches ideal for an

  Brian Moon Keller Williams ONEChicago

  1317 W Elmdale Ave, Chicago, IL 60660
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  /8

  $299,900

  Pending

  • 6 Beds
  • 3 Baths

  8236 S May St, Chicago, IL 60620

  Excellent Investment Opportunity in Auburn Gresham. Discover the potential in this solid all-brick 2-unit property located in the Auburn Gresham neighborhood. Each unit offers 3 bedrooms and 1 bathroom with functional layouts, well-maintained, providing a strong foundation for rental income or owner-occupant use. The property also features a full basement, offering additional possibilities for

  Deonte Barbee Real Broker LLC

  8236 S May St, Chicago, IL 60620
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  /4

  $224,900

  $12K PRICE DROP

  • 6 Beds
  • 2 Baths

  1806 S Homan Ave, Chicago, IL 60623

  *Attention investors!* This is an opportunity for buyers seeking a project or investment property. This property is being sold as-is via Xome auction and is currently occupied. No access will be provided to the property, do not disturb occupants. The sale is subject to auction terms and conditions. Seller does not provide survey. Buyer to verify zoning and take subject to any municipal

  Anthony Disano Parkvue Realty Corporation

  1806 S Homan Ave, Chicago, IL 60623
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  /2

  $240,000

  • 7 Beds
  • 2 Baths

  Unlisted Address

  This two-unit property is a work in progress, offering the perfect canvas for a savvy investor, contractor, or handyman looking to add value. The building features two spacious units-one with 4 bedrooms and 1 bathroom, and the second with 3 bedrooms and 1 bathroom-providing strong potential for rental income or a live-in investment. With an unfinished basement and renovations already underway,

  Victor Jimenez Berkshire Hathaway HomeServices American Heritage

  Unlisted Address
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  /25

  $270,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath

  212 E Cullerton St Unit 607, Chicago, IL 60616

  Welcome to loft living in the historic Prairie District of Chicago's South Loop. This spacious one-bedroom soft loft features an unusually large bedroom with a walk-in closet, an open-concept living area, and beautiful, unobstructed western exposure showcasing spectacular sunset and downtown skyline views. A wall of floor-to-ceiling windows fills the home with natural light, while the private

  Colleen Harper @properties Christie's International Real Estate

  212 E Cullerton St Unit 607, Chicago, IL 60616
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  /12

  $1,080,000

  2904 S Wells St, Chicago, IL 60616

  Excellent investment opportunity in the desirable neighborhood! This well-maintained multi-unit property features a total of 7 residential units , offering multiple streams of rental income. The front building includes a 3 bed/1 bath unit on the first floor, a 2 bed/1 bath unit on the second floor, and a 1 bed/1 bath unit on the third floor, while the rear building consists of three 2 bed/1 bath

  Qian Kun Chen Kale Realty

  2904 S Wells St, Chicago, IL 60616
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  /22

  $367,000

  $2K PRICE DROP

  • 5 Beds
  • 2 Baths

  7546 S Sangamon St, Chicago, IL 60620

  Exceptional Investment Discover this beautifully modernized 2-unit property offering the perfect blend of comfort, style, and location. The 1st floor offers a spacious unit with 2 bedrooms and 1 bath, thoughtfully updated with hardwood floors throughout, granite countertops, and stainless-steel appliances, providing a sleek and contemporary living experience. The 1st floor is elegant and classy

  Siobhan Robinson Mobile Realty LLC

  7546 S Sangamon St, Chicago, IL 60620
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  /50

  $350,000

  Pending

  • 4 Beds
  • 2 Baths

  6556 S Woodlawn Ave, Chicago, IL 60637

  Located in the heart of the highly sought-after Woodlawn neighborhood, this property presents an incredible opportunity to own in one of Chicago's fastest-growing communities. Just minutes from the University of Chicago, Jackson Park, the future Obama Presidential Center, and the lakefront, this location continues to attract attention for its growth, convenience, and long-term potential.

  Ivan Blanco eXp Realty

  6556 S Woodlawn Ave, Chicago, IL 60637
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  /32

  $280,000

  $45K PRICE DROP

  • 8 Beds
  • 4 Baths

  Unlisted Address

  Bring your vision to life with this unique brick multifamily investment opportunity on a prominent corner lot in Chicago's Austin neighborhood. Currently configured as a 4-unit property and situated on two PINs, the building includes a partially finished basement with two additional units. Fully vacant and ready for renovation, this property provides investors and developers with the advantage of

  Anthony Kirkland Coldwell Banker Realty

  Unlisted Address
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  /16

  $200,000

  $35K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 860 Sq Ft

  200 N Dearborn St Unit 1002, Chicago, IL 60601

  FULL AMENITY CONDO IN HEART OF DOWNTOWN! ONE BED ROOM UNIT WITH OPEN FLOOR PLAN, LOT OF CLOSET SPACE. GREAT FOR SOMEONE WHO WORKS DOWNTOWN OR AS 2ND HOME IN THE CITY. STEPS TO MICHIGAN AVE, THEATER DISTRICT, MILLENNIUM PARK & MORE! PEDWAY CONNECTS TO NUMEROUS BUILDINGS INCLUDING MACY'S, DALEY CENTER, HOTELS, RESTAURANTS, SHOPS & PUBLIC TRANSPORTATION. THE UNIT NEED SOME WORK. THE PRICE REFLECTION

  Joyce Yamei Chen Concentric Realty, Inc

  200 N Dearborn St Unit 1002, Chicago, IL 60601
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  /2

  $7,900

  $4K PRICE DROP

  • Land
  • 0 Sq Ft

  8040 S Exchange Ave, Chicago, IL 60617

  May contact directly with owner at 7737475025 (Broker owned). THIS LISTING WILL ONLY BE UP FOR ABOUT A WEEK. DON'T MISS OUT! Best value in the area. Huge potential. RT-4, 3025 sqft. Walking distance to new huge development. Advocate Health just broke ground on nearby hospital with reports that it will be a $1 billion investment. Every block of proximity to development matters. A little further

  Yohan Hwang Core Realty & Investments Inc.

  8040 S Exchange Ave, Chicago, IL 60617
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  /9

  $59,900

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  8136 S Drexel Ave Unit 2, Chicago, IL 60619

  Attention smart buyers and investors!!!!!! Welcome to your new urban sanctuary or your immediate cash flow investment! Unbeatable value on Chicago's South Side! This ready-to-go 2-bedroom condo in Chatham is perfect for a first-time homebuyer or savvy investor. Featuring a smart layout, this unit is located in a highly efficient, low-upkeep building that makes living easy. Incredible location

  Dreena Jones Keller Williams Preferred Realty

  8136 S Drexel Ave Unit 2, Chicago, IL 60619
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  /29

  $209,900

  • 4 Beds
  • 4 Baths

  11420 S Champlain Ave, Chicago, IL 60628

  Incredible investment opportunity in Historic Pullman! Soid 4 Unit, 2 story brick building located in the sought after Pullman neighborhood. Each unit offers 1 bedroom and 1 bathroom, presenting excellent income potential for investors or owner occupants alike. Property features a full finished basement and a 2 car garage, adding valuable space and utility. This property needs work and is ready

  Michael Olszewski Area Wide Realty

  11420 S Champlain Ave, Chicago, IL 60628
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  /33

  $149,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,181 Sq Ft

  10122 S Luella Ave, Chicago, IL 60617

  Welcome to this charming brick home offering 3 bedrooms, 1 bathroom, and approximately 1,200 square feet of comfortable living space. Brand new flooring adds warmth and character throughout much of the home, while the functional floor plan provides plenty of space for everyday living. A full unfinished basement offers endless possibilities for storage, a workshop, or future expansion. Situated on

  Samantha Swaney GC Realty and Development

  10122 S Luella Ave, Chicago, IL 60617
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  /21

  $349,999

  Pending

  • 7 Beds
  • 2 Baths

  6525 S Peoria St, Chicago, IL 60621

  Excellent investment opportunity! This solid brick 2-unit building offers spacious layouts with approximately 2,596 square feet of living space. Each unit features generous room sizes, making it ideal for owner-occupants or investors looking to generate rental income. Property includes a full basement, detached garage, and a private backyard. Conveniently located near schools, parks, public

  Robert Los HomeSmart Connect LLC

  6525 S Peoria St, Chicago, IL 60621
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  /3

  $80,000

  • 4 Beds
  • 1 Bath

  321 E 116th St, Chicago, IL 60628

  Great investment opportunity with plenty of potential. This multi-level property features a spacious layout, new rear porch & convenient location. New rear porch. Each unit has living room, kitchen & 2 bedrooms. Basement & attic open unfinished. Sold "as-is".

  Carlos Patino RE/MAX Mi Casa

  321 E 116th St, Chicago, IL 60628
• 

  

  /22

  $479,999

  Pending

  • 8 Beds
  • 4 Baths

  9032 S Laflin St, Chicago, IL 60620

  4 Unit Brick building. Each unit is spacious and have nice size bedrooms. Also, a carport for 4 parking spaces available for 4 cars. Two units vacant. Two has rental income. One unit is on a MTM. Building has plenty of storage in basement with laundry. New roof and forced heating. Investment opportunity.

  Kimberly Hicks EXIT Strategy Realty

  9032 S Laflin St, Chicago, IL 60620
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  /34

  $359,000

  • 6 Beds
  • 2 Baths

  4505 S Justine St, Chicago, IL 60609

  Welcome to this beautifully recently remodeled, all-brick 2-flat offering an excellent opportunity for investors or owner-occupants! Both units feature 3 bedrooms and 1 bathroom, with generously sized living rooms, formal dining areas, hardwood flooring, and contemporary kitchens featuring European-style cabinetry, quartz countertops, full glass-tile backsplashes, and newer appliances. The

  Qizhong Guan Century 21 S.G.R., Inc.

  4505 S Justine St, Chicago, IL 60609

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