Investment - Homes for Sale in Chicago, IL

• 

  

  

  /11

  $126,000

  Pending

  • 2 Beds
  • 1 Bath
  • 842 Sq Ft

  742 E 105th St, Chicago, IL 60628

  Cash-Flowing Investment Opportunity in the Pullman Area! Townhouse-style home offering strong investment potential and immediate rental income. This brick property features a functional layout with a spacious Living Room, Dining Room, Kitchen, 2 Bedrooms, 1 Full Bath, plus an additional basement room currently being used as a bedroom. The property is tenant-occupied on a month-to-month lease at

  Jermaine McGee Premier Midwest Realty, INC

  742 E 105th St, Chicago, IL 60628
• 

  

  

  /38

  $449,000

  • 8 Beds
  • 3 Baths

  7049 S Vernon Ave, Chicago, IL 60637

  Discover a distinctive renovated multi-family residence offering two generously scaled units refined with contemporary updates and elevated finishes. Ideal for buyers seeking space, flexibility, and sophisticated design in a multi-unit setting. The First floor home features five bedrooms, two baths, set up with 2 bedrooms on first floor and 3 bedrooms downstair and the duplex layout extending

  Rudy Gandy Premier Agent Network Illinois LLC

  7049 S Vernon Ave, Chicago, IL 60637
• 

  

  /2

  $23,000

  $4K PRICE INCREASE

  • Land
  • 0 Sq Ft

  4904 S Princeton Ave, Chicago, IL 60609

  Exceptional Opportunity for Investors and Home Builders This is a rare chance to purchase a buildable lot in Chicago's Fuller Park neighborhood, just minutes from downtown. In addition to this parcel, the same owners are also offering 3 other nearby lots, each with its own Property Identification Number (PIN) and separate price. These additional lots are not included in the price of the property

  Spasoje Bjelica City Realtor INC.

  4904 S Princeton Ave, Chicago, IL 60609
• 

  

  

  /21

  $1,250,000

  Pending

  • 7 Beds
  • 4 Baths

  1446 W Catalpa Ave, Chicago, IL 60640

  Classic Chicago two-flat in the heart of Andersonville, thoughtfully updated in 2025 to blend modern amenities with timeless vintage charm. An exceptional investment opportunity, this property is ideal as a live-in, owner-occupied home with rental income or as a fully leased, income-producing asset. The second-floor two-bedroom apartment features central A/C, in-unit laundry, and a beautifully

  Philip Skowron Compass

  1446 W Catalpa Ave, Chicago, IL 60640
• 

  

  

  /58

  $399,999

  • 10 Beds
  • 4 Baths

  2243 S Sawyer Ave, Chicago, IL 60623

  Turnkey investment opportunity in the heart of the vibrant South Lawndale neighborhood! This well-maintained and updated 4-unit building is perfect for investors looking to generate strong rental income from day one. Each unit features updated kitchens with granite countertops, offering modern finishes that tenants love. The property has been thoughtfully improved with major updates completed

  Luis Ortiz RE/MAX Partners

  2243 S Sawyer Ave, Chicago, IL 60623
• 

  

  /22

  $849,000

  New Construction Pending

  • 9 Beds
  • 6 Baths

  3119 W Flournoy St, Chicago, IL 60612

  Exceptional investment or owner-occupant opportunity with this coming soon new construction three-unit property featuring modern finishes and thoughtful design throughout. Each spacious unit offers 3 bedrooms and 2 full baths. Step inside to find open-concept layouts with abundant natural light, in-unit laundry, and stainless steel appliances in every kitchen. A rear parking pad provides

  Lawrence Dunning Fulton Grace Realty

  3119 W Flournoy St, Chicago, IL 60612
• 

  

  /78

  $445,000

  • 5 Beds
  • 3 Baths
  • 2,821 Sq Ft

  543 N Leclaire Ave, Chicago, IL 60644

  An exceptional opportunity to own a spacious four-level home offering approximately 2,821 square feet in one of Chicago's fastest-growing neighborhoods. Designed for today's lifestyle, this stunning residence features 5 generously sized bedrooms, 3 full bathrooms, expansive living and entertaining spaces, and quality craftsmanship throughout. The beautifully appointed kitchen showcases white

  Michael Applegate Straight-A Realty, LLC

  543 N Leclaire Ave, Chicago, IL 60644
• 

  

  /34

  $1,175,000

  Pending

  • 7 Beds
  • 5 Baths

  2115 W Wellington Ave, Chicago, IL 60618

  Great investment opportunity in Roscoe Village on an oversized lot! All units updated with newer kitchens and baths, central A/C and washer/dryer in unit. Tenants pay their own electric and gas. All units currently leased, but easy opportunity to become an owner occupant. Second floor front unit is a spacious duplex up that makes a wonderful owner's unit. Total current annual rent income of

  Barbara Allen Metru Real Estate LLC

  2115 W Wellington Ave, Chicago, IL 60618
• 

  

  /27

  $475,000

  $25K PRICE DROP

  • 5 Beds
  • 3 Baths

  2320 S Albany Ave, Chicago, IL 60623

  This stunning two-unit multifamily property boasts spacious and beautiful interiors. It features a new roof, siding, and several interior updates. With a total of 5 bedrooms and 3 full bathrooms, each unit comes with its own laundry space. It's the ideal investment opportunity!

  Andres Olaez Keller Williams ONEChicago

  2320 S Albany Ave, Chicago, IL 60623
• 

  

  /12

  $180,000

  $49K PRICE DROP

  • 8 Beds
  • 3 Baths

  4150 W Carroll Ave, Chicago, IL 60624

  Outstanding opportunity to complete and customize this spacious West Garfield Park multi-unit property. Major improvements have already been started, with several rooms featuring fresh paint, updated windows, and new finishes, while additional renovations remain to unlock the property's full potential. The home offers generous living space, large bedrooms, a full basement for storage or future

  Landon Kelly Real Broker, LLC

  4150 W Carroll Ave, Chicago, IL 60624
• 

  

  /20

  $400,000

  • 9 Beds
  • 5 Baths

  8305 S Throop St, Chicago, IL 60620

  If you know you KNOW, Auburn Gresham is EVOLVING! Owner-Occupant or Investor Opportunity | 4 Unit + 1 more income producing basement unit that has two entrances! Solid brick 4 flat building featuring 9 bedrooms and 5 bathrooms, offering exceptional flexibility and income opportunity. Property is currently tenant-occupied; however, the 1st-floor unit will be delivered vacant at closing, creating

  Dana Jones Century 21 IMPACT

  8305 S Throop St, Chicago, IL 60620
• 

  

  /13

  $525,000

  $24K PRICE DROP

  • 15 Beds
  • 4 Baths

  1311 S Harding Ave, Chicago, IL 60623

  Turnkey investment opportunity in the heart of North Lawndale! This recently remodeled 4-unit brick building sits on a well-kept block and offers strong income potential for both seasoned investors and owner-occupants alike. Each unit features its own separate furnace and hot water tank, providing efficiency, convenience, and reduced operating expenses. The property has been thoughtfully updated,

  Alexander Summers Triton Realty Group LLC

  1311 S Harding Ave, Chicago, IL 60623
• 

  

  /32

  $699,999

  Pending

  • 4 Beds
  • 2 Baths

  2846 N Elston Ave, Chicago, IL 60618

  Located in the heart of Avondale, this well-maintained 2-flat with a non-conforming garden unit offers an ideal blend of investment potential and owner-occupant appeal. Just steps from popular coffee shops, craft breweries, restaurants, and multiple grocery options, the location continues to attract strong tenant demand. The spacious first-floor unit features soaring 10-foot ceilings and an open

  Elias Masud Compass

  2846 N Elston Ave, Chicago, IL 60618
• 

  

  /33

  $229,900

  • 6 Beds
  • 3 Baths

  1 E 114th St, Chicago, IL 60628

  Welcome to your new home! This spacious brick corner-lot property offers plenty of room for a large family and is packed with updates and investment potential. The home features 6 generously sized bedrooms, 3 full bathrooms, and a dedicated office/study. Enjoy a comfortable living room with a fireplace, a beautifully updated kitchen with granite countertops and new stainless steel appliances, and

  Ola Sanni Century 21 S.G.R., Inc.

  1 E 114th St, Chicago, IL 60628
• 

  

  /21

  $134,999

  Pending

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft

  10149 S Wentworth Ave, Chicago, IL 60628

  Great investment opportunity! This 3-bedroom, 2-bath bungalow offers hardwood floors, a spacious upper level, and a primary bedroom with ensuite bath. Features include newer windows, a newer furnace, and a hot water heater installed in April 2026. The kitchen features a center island and stainless steel appliances, and the property includes a fenced backyard. Excellent opportunity for investors,

  Tracy Ammons Ani Real Estate

  10149 S Wentworth Ave, Chicago, IL 60628
• 

  /2

  $300,000

  Pending

  • 4 Beds
  • 2 Baths
  • 906 Sq Ft

  4149 W Fullerton Ave, Chicago, IL 60639

  Welcome to this charming 4 bed 2 bath investors dream or a new homeowners blank canvas. This home boasts two bedrooms large enough for king sized beds on the second floor, and two cozy first floor bedrooms perfect for a guest or inlaw. The full unfinished basement is just waiting to be your rec room. The eat in kitchen and combined living dining room offer ample space for parties and guests. A

  Matthew Johnston Fulton Grace Realty

  4149 W Fullerton Ave, Chicago, IL 60639
• 

  /2

  $630,000

  Pending

  • 10 Beds
  • 2 Baths

  4742 N Kewanee Ave, Chicago, IL 60630

  Welcome to this beautifully renovated 2-flat nestled in the highly sought-after Mayfair neighborhood! This turnkey investment opportunity seamlessly blends modern updates with timeless character, making it ideal for both owner-occupants and savvy investors. Each spacious unit has been thoughtfully remodeled with quality finishes, featuring updated kitchens, stylish bathrooms, refinished flooring,

  Zain Nasir ERA Partners

  4742 N Kewanee Ave, Chicago, IL 60630
• 

  

  /45

  $650,000

  Pending

  • 4,943 Sq Ft

  6058 S Massasoit Ave, Chicago, IL 60638

  6058 S Massasoit Ave is a solid, all-brick 6-unit apartment building located in the highly desirable Midway Clearing/Garfield Ridge area neighborhood. This property offers a reliable investment opportunity with a strong rent roll, generating $5,975 in monthly income and a total of $71,700 annually. The building consists of 3 one bedroom apartments - and 3 two-bedroom apartments. On-site

  Sergio Hernandez Keller Williams Premiere Properties

  6058 S Massasoit Ave, Chicago, IL 60638
• 

  

  /18

  $270,000

  • 3 Beds
  • 1.5 Baths

  3544 W 63rd Place, Chicago, IL 60629

  Welcome to this well maintained Chicago home located in the heart of West Lawn! This property offers spacious living areas, generous bedroom sizes, and a functional layout perfect for owner-occupants or investors alike. Conveniently situated near schools, parks, shopping, restaurants, and public transportation, with easy access to major expressways. Whether you're looking for your next home or a

  Emily Roman Realty of America, LLC

  3544 W 63rd Place, Chicago, IL 60629
• 

  

  /16

  $499,999

  • 5 Beds
  • 4 Baths

  2341 N Merrimac Ave, Chicago, IL 60639

  Classic Chicago bungalow offering the versatility of a legal 2-unit plus a finished basement, providing exceptional flexibility for owner-occupants, multigenerational living, or investors alike. This home blends the timeless appeal of a classic Chicago bungalow with the practical layout of a multi-unit property. Each unit offers comfortable living space filled with natural light, while the

  Corina Flores-Moradi Re/Max Cityview

  2341 N Merrimac Ave, Chicago, IL 60639
• 

  

  /21

  $489,000

  $24K PRICE INCREASE Pending

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  600 N Kingsbury St Unit 906, Chicago, IL 60654

  An exceptional investment opportunity with a CAP rate of 6.49% in the heart of River North, a spacious 2-bedroom, 2-bath home can deliver immediate rental income and the kind of consistent demand investors love with a lease that extends through June 30, 2027. The unit showcases sweeping skyline views through floor-to-ceiling windows and opens onto a generous balcony-an inviting place to pause,

  Erin Booker Engel & Voelkers Chicago North Shore

  600 N Kingsbury St Unit 906, Chicago, IL 60654
• 

  

  /25

  $849,000

  $26K PRICE DROP Pending

  • 4 Beds
  • 3 Baths

  1520 N Campbell Ave, Chicago, IL 60622

  Prime investment opportunity or multi-generational home in Chicago's vibrant West Town/East Humboldt neighborhood. This recently renovated light filled 2-unit building offers 3 bedrooms 2 bathrooms on the main level in addition to laundry room, dining/ living, and pantry, glass slider, and steel deck perfect for parties and entertaining. The ground level unit consists of 1 bed 1 bath ideal for

  Anthony White EXIT Strategy Realty

  1520 N Campbell Ave, Chicago, IL 60622
• 

  

  /29

  $1,600,000

  • 9 Beds
  • 4 Baths

  2838 N Sheffield Ave, Chicago, IL 60657

  Beautifully maintained and thoughtfully updated, this classic Chicago three-flat is located in the heart of Lakeview. Ideal for investors or owner-occupants, the property offers a great "house hacking" setup-live in the spacious owner's duplex-down while generating rental income from the two generously sized upper units. Throughout the building, vintage character is paired with modern

  Eugene Fu @properties Christie's International Real Estate

  2838 N Sheffield Ave, Chicago, IL 60657
• 

  

  /27

  $1,100,000

  • 10 Beds
  • 3 Baths

  1657 N Artesian Ave, Chicago, IL 60647

  Welcome to 1657 N Artesian in Chicago this is a classic two-flat featuring a solid brick coach house at the rear of the property, offering a rare and versatile investment opportunity. Situated on a single PIN, the property is ideal for developers or investors looking to convert the buildings into condominiums or undertake a unique redevelopment project. Schedule your appointment today!!

  Monica Morales Extreme Realty LLC

  1657 N Artesian Ave, Chicago, IL 60647
• 

  

  /15

  $290,000

  Pending

  • 12 Beds
  • 4 Baths

  7321 S Stewart Ave, Chicago, IL 60621

  GREAT INVESTMENT OPPORTUNITY!!! 2 units are vacant and 2 units are rented month 2 month 12 bds, 4 bth, 4908 sqft Year built 1900 Condition per the seller Plumbing & Electrical: Owner states there are no issues with the plumbing or electrical systems. Foundation: Owner confirmed there are no foundation issues. General Painting: At least one apartment needs a full paint job. Drywall Work: One unit

  Airreca Weaver Coldwell Banker Real Estate Group

  7321 S Stewart Ave, Chicago, IL 60621
• 

  

  /14

  $199,000

  • 5 Beds
  • 2 Baths

  11633 S Parnell Ave, Chicago, IL 60628

  Fully occupied 2-flat ready for a new owner. This property generates $3,350/mo in total monthly rents and offers multiple investment strategies: buy-and-hold, value add, or owner occupy / house hack. Both units feature hardwood floors, spacious living/dining areas and functional layouts. A full unfinished basement provides expansion potential, plus a detached 2-car garage. Conveniently located

  Michael Scanlon eXp Realty

  11633 S Parnell Ave, Chicago, IL 60628
• 

  

  /12

  $570,000

  • 11 Beds
  • 5 Baths

  1239 S Avers Ave, Chicago, IL 60623

  Exceptional House Hack Opportunity in North Lawndale - 3 Unit Building | 11 Bedrooms | 5 Bathrooms Incredible opportunity to own a cash-flowing 3-unit property with 11 bedrooms and 5 bathrooms located at 1239 S Avers Ave in Chicago's rapidly developing North Lawndale neighborhood. This oversized multi-unit building offers the perfect setup for a house hacker looking to live in one unit while

  Melchor Domantay Second City Real Estate

  1239 S Avers Ave, Chicago, IL 60623
• 

  

  /22

  $605,000

  $45K PRICE DROP

  • 7 Beds
  • 2 Baths

  4339 S Indiana Ave, Chicago, IL 60653

  Welcome to a spacious vintage home with all the amenities of luxurious city living. Located In up and coming historic Bronzeville, just south of downtown, this gem boasts two generous units with high ceilings and spacious living and dining areas. This exceptional property blends classic Chicago character with all the modern comforts of a home. Whether you seek a strong investment opportunity or a

  Henry Torn ListWithFreedom.com

  4339 S Indiana Ave, Chicago, IL 60653
• 

  

  /23

  $1,200,000

  • 9 Beds
  • 3 Baths

  936 N Fairfield Ave, Chicago, IL 60622

  Prime Turnkey Investment Opportunity! Classic Graystone 3-Flat Steps from Wicker Park & Ukrainian Village & Humboldt Park Rare graystone 3-unit offering 1,100+ sq. ft. per apartment, each with 3 true bedrooms-highly desirable in one of Chicago's strongest rental corridors. Long-term tenants are on month-to-month leases, giving buyers the flexibility to update units, raise rents to current market

  Alexandra Garcia Real People Realty

  936 N Fairfield Ave, Chicago, IL 60622
• 

  

  /3

  $15,000

  • Land
  • 0 Sq Ft

  6507 S Marshfield Ave, Chicago, IL 60636

  Attention builders, developers, and investors! Fantastic opportunity to acquire this 25x123 lot zoned RS-3 in an area experiencing continued residential growth and redevelopment. Perfect opportunity for new construction or long-term investment potential. Conveniently located near schools, parks, public transportation, shopping, and major roadways.Drive by and explore the possibilities this

  Christopher Anthony Keller Williams ONEChicago

  6507 S Marshfield Ave, Chicago, IL 60636
• 

  

  /23

  $525,000

  Pending

  • 9 Beds
  • 3 Baths

  7018 S Dorchester Ave, Chicago, IL 60637

  Take advantage of this outstanding opportunity to own a well-maintained 3-unit investment property in the heart of Chicago's thriving South Side. Ideally located near the Obama Presidential Center and surrounded by significant neighborhood revitalization, this property offers excellent income potential with room for growth. The building features three spacious units, each offering 3 bedrooms and

  Jean Walker Redfin Corporation

  7018 S Dorchester Ave, Chicago, IL 60637
• 

  

  /53

  $1,199,900

  Pending

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

  2868 N Orchard St, Chicago, IL 60657

  Exceptional East Lakeview corner townhome offering three bedrooms, a penthouse level lofted family room, extensive recent upgrades, remarkable outdoor living spaces, and the rare benefit of no monthly HOA assessments. Perfectly situated on a quiet tree-lined street just moments from the lakefront, this meticulously maintained residence blends sophisticated interiors with over-the-top private

  Leigh Marcus @properties Christie's International Real Estate

  2868 N Orchard St, Chicago, IL 60657
• 

  /2

  $659,000

  $90K PRICE INCREASE

  • Land
  • 0 Sq Ft

  2613-2633 N Cicero Ave, Chicago, IL 60641

  On a busy Cicero Aveneue between Diversy and Fullerton, this 9,375 square foot parcel is available for sale. The land could be developed for a wide variety of retail uses. The site has low taxes for the area with substantial frontage on Cicero Avenue with easy access to bustling Six Corners. Great opportunity for a user or developer. The Belmont Cragin community has benefited from steady growth

  Daniel Hyman Millennium Properties RE, Inc.

  2613-2633 N Cicero Ave, Chicago, IL 60641
• 

  

  /28

  $559,900

  Pending

  • 7 Beds
  • 4 Baths

  2924 S Princeton Ave, Chicago, IL 60616

  Prime investment opportunity in Chicago's sought-after south-side corridor. This well-maintained 4-unit building at 2924 S Princeton Ave offers strong cash flow with upside, just minutes away from vibrant neighborhoods, transit, and everyday conveniences. The property comprises four spacious units totaling 7 bedrooms, 4 bathrooms, and a detached 2.5 car garage. Brick exterior, solid mechanicals,

  Bernardo Casas Duarte Realty Company

  2924 S Princeton Ave, Chicago, IL 60616
• 

  

  /44

  $335,000

  Pending

  • 5 Beds
  • 2 Baths

  4912 W Fulton St, Chicago, IL 60644

  Great investment opportunity in the Austin neighborhood! This property needs some TLC and offers strong potential for renovation, rental income, or value-add investment. Buyer and buyer's agent to conduct their own due diligence prior to submitting an offer. Located on Chicago's West Side, the property has convenient access to public transit (CTA Green Line & buses), parks and recreation nearby

  Karolina Bak KOMAR

  4912 W Fulton St, Chicago, IL 60644
• 

  

  /40

  $439,000

  Pending

  • 6 Beds
  • 3 Baths

  3005 S Pulaski Rd, Chicago, IL 60623

  Excellent opportunity to own this updated multi-unit property in a prime location and lots of updates! The building features two, 2-bedroom units, each offering a comfortable layout with bright living areas, eat-in kitchens, and generous room sizes. The garden level offers additional living space with 2 bedrooms. Newer flooring, utilities including a brand new central HVAC system, brand new

  Maggie Antillon Realty of America, LLC

  3005 S Pulaski Rd, Chicago, IL 60623
• 

  

  /14

  $350,000

  $20K PRICE DROP Pending Pre-Foreclosure

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft

  235 W Van Buren St Unit 1615, Chicago, IL 60607

  Modern high-rise living in the heart of the Loop! Spacious 2-bed/2-bath with floor-to-ceiling windows, private corner balcony, and sweeping west-facing views of the river and sunsets. Open kitchen features granite counters and stainless appliances flowing into a bright living area. Both bedrooms are fully enclosed with windows, closets, and solar shades. Primary suite with ample storage. In-unit

  Jennifer Wadhwa Jason Mitchell Real Estate IL

  235 W Van Buren St Unit 1615, Chicago, IL 60607
• 

  

  /40

  $885,000

  • 9 Beds
  • 7 Baths

  1527 E 66th Place, Chicago, IL 60637

  Prime Woodlawn Investment Opportunity! Invest in the growth of Chicago's historic Woodlawn neighborhood with this meticulously maintained, condo-quality 3-unit building. Perfectly positioned just blocks from the Obama Presidential Center, this turn-key property is an exceptional opportunity to owner occupy or invest, offering high-end rental income and significant long-term appreciation

  Wayne Beals Exit Strategy Realty / EMA Management

  1527 E 66th Place, Chicago, IL 60637
• 

  

  /14

  $180,000

  Pending

  • 2 Beds
  • 2 Baths

  Unlisted Address

  Attention rehabbers, contractors, perfect investment opportunity in fabulous appreciating area for investors and or live-in owners looking for solid rental income in high rental demand area. 2 units with separate utilities plus tall unfinished attic. Bring your ideas to this solid brick home and bring it back with value growth potential. Newer windows on both floors 2023. Tear-off roof 2021 and

  Maribel Selva Coldwell Banker Realty

  Unlisted Address
• 

  

  /15

  $245,000

  $24K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  7518 S Union Ave, Chicago, IL 60620

  Welcome home to this spacious and versatile 4-bedroom, 1.5-bath residence offering plenty of room for comfortable living and exceptional investment potential. The main level features a bright and inviting family room, a formal dining room perfect for entertaining, and a functional layout designed to accommodate a variety of lifestyles. The finished basement adds valuable living space and can be

  Abiturab Mithaiwala Heart My Home Chicago Inc

  7518 S Union Ave, Chicago, IL 60620

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