Investment - Homes for Sale in Chicago, IL

• 

  

  

  /36

  $500,000

  • 4 Beds
  • 3 Baths

  2948 N Narragansett Ave, Chicago, IL 60634

  **Listing reactivated due to previous buyer's failure to perform; the inspection and appraisal were both completed successfully, with no related issues reported.** Outstanding owner-occupant or investment opportunity in Chicago's Montclare neighborhood! Fully updated in 2021, this well-maintained two-unit property offers 4 bedrooms, 3 full bathrooms and approximately 2,837 square feet of total

  

  Cecil Sabu

  ALLURE Real Estate

  2948 N Narragansett Ave, Chicago, IL 60634
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• 

  

  

  /15

  $165,555

  • 2 Beds
  • 2 Baths
  • 1,322 Sq Ft

  1469 E 69th St Unit 2, Chicago, IL 60637

  Welcome to 1469 E 69th Street-a move-in-ready 2-bedroom, 2-bath condo offering an affordable entry point into one of Chicago's most exciting areas. Priced to sell-with a low $175 monthly HOA, this property makes sense whether you're looking for a place to call home or your next investment. Enjoy comfortable living today while leaving plenty of opportunity to build equity through future cosmetic

  

  Melanie Miller

  Keller Williams ONEChicago

  1469 E 69th St Unit 2, Chicago, IL 60637
• 

  

  /2

  $17,000

  • Land
  • 0 Sq Ft

  11818 S Lafayette Ave, Chicago, IL 60628

  Excellent opportunity to own a vacant residential lot at 11818 S Lafayette Ave in Chicago's West Pullman neighborhood. This attractive, level parcel offers a spacious grassy setting surrounded by mature trees and established residential properties. Whether you're a builder, investor, or future homeowner, this is a great chance to secure land and bring your vision to life. The property offers

  

  Jason Rosenberg

  Infiniti Properties, Inc.

  11818 S Lafayette Ave, Chicago, IL 60628
• 

  

  

  /25

  $659,000

  Pending

  • 10 Beds
  • 6 Baths

  2205 N Melvina Ave, Chicago, IL 60639

  Fantastic investment opportunity! Well-maintained multi-unit property featuring a 3-unit building plus a coach house with an additional apartment. The main building offers two 2-bedroom units, one with 1 bath and the other with 2 baths and a rear porch area, plus a spacious 3-bedroom, 1-bath unit. The coach house features 3 bedrooms and 1 bath. Each unit offers a living room and dining room,

  

  Maria Miller

  Better Homes & Gardens Real Estate

  2205 N Melvina Ave, Chicago, IL 60639
• 

  

  

  /44

  $650,000

  Pending

  • 8 Beds
  • 3 Baths

  852 N Springfield Ave, Chicago, IL 60651

  Incredible investment opportunity or perfect owner-occupant setup in Chicago's booming Humboldt Park! This gorgeous brick two-flat seamlessly blends classic vintage character with modern convenience. Both principal units are completely move-in ready and feature original, gleaming hardwood floors, timeless woodwork, and abundant natural charm throughout. The property boasts massive added value

  

  Gina Joshi

  Prestige Realty Group

  852 N Springfield Ave, Chicago, IL 60651
• 

  

  /17

  $219,000

  • 5 Beds
  • 1 Bath
  • 1,039 Sq Ft

  5134 S Wolcott Ave, Chicago, IL 60609

  Rare 5-bedroom single-family home offering plenty of space for a growing family or a great investment opportunity. Recent updates include a newer roof, ceramic tile flooring, fresh paint, and a new security screen door leading to the fully fenced backyard. The outdoor space is ideal for entertaining, gatherings, pets, or play. With solid updates already in place, this home is ready for your

  

  Brandice Hampton

  Baird & Warner

  5134 S Wolcott Ave, Chicago, IL 60609
• 

  

  /15

  $149,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  6315 S Troy St, Chicago, IL 60629

  **Great Investment Opportunity - Sold As-Is! ** Unlock the potential of this corner property situated on an oversized lot with alley access. Whether you're an investor, rehabber, or buyer looking to create your dream home, this property offers endless possibilities. The home features **3 bedrooms and 2 full bathrooms**, along with an abundance of outdoor space including a **front yard, side yard,

  

  Edgar R. Guerrero

  REMAX Legends

  6315 S Troy St, Chicago, IL 60629
• 

  

  /4

  $549,000

  4355 W Le Moyne St, Chicago, IL 60651

  Exceptional investment opportunity in the heart of Humboldt Park! This solid 5-unit building at 4355 W Le Moyne St is a rare find for investors, developers, or savvy buyers looking to add value. The property is currently fully vacant, offering a blank slate to design, renovate, and maximize rental income or pursue a condo conversion. The building requires renovation, but its strong bones and

  

  Israel Valadez

  Realty of America, LLC

  4355 W Le Moyne St, Chicago, IL 60651
• 

  /2

  $295,000

  Pending

  • 7 Beds
  • 2 Baths

  427 N Lawndale Ave, Chicago, IL 60624

  Discover an outstanding investment or owner-occupant opportunity with this beautifully updated brick two-flat nestled on a quiet, tree-lined dead-end street in the heart of Humboldt Park. Perfectly positioned just steps from the Garfield Park Conservatory, this well-maintained property combines strong rental potential with an unbeatable location. Each spacious unit offers generous living space,

  

  Rafay Qamar

  Real Broker LLC

  427 N Lawndale Ave, Chicago, IL 60624
• 

  

  /18

  $1,299,000

  • 4 Beds
  • 5 Baths

  2127 N Winchester Ave, Chicago, IL 60614

  Exceptional investment opportunity in Chicago's Bucktown neighborhood. This fully rented three-unit walkup offers strong income potential and modern finishes throughout, making it an ideal addition to any investor's portfolio. The property consists of two 1-bedroom, 1-bathroom units and a spacious 2-bedroom, 2.5-bathroom duplex owner's unit. All three apartments feature stone countertops,

  

  Erik Schwab

  Corcoran Urban Real Estate

  2127 N Winchester Ave, Chicago, IL 60614
• 

  

  /36

  $429,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths

  3504 S Maplewood Ave, Chicago, IL 60632

  This charming two-unit building at 3504 S. Maplewood St. offers an excellent investment or owner-occupied opportunity, featuring two spacious units each with two bedrooms and one bathroom. Both units have been fully updated with new kitchens, fresh paint, and new appliances, providing modern comfort and move-in readiness. The property also includes a two-car garage and a large backyard, perfect

  

  Evan Peng

  Landmark Property Group Realty, LLC

  3504 S Maplewood Ave, Chicago, IL 60632
• 

  

  /12

  $99,000

  Pending

  • 4 Beds
  • 2 Baths

  9737 S Prairie Ave, Chicago, IL 60628

  Attention Buy-and-Hold Investors-Your Next Project Starts Here! Some properties are looking for a fresh coat of paint, this one is looking for a fresh start. Welcome to 9737 S Prairie Ave, a classic brick 2-flat offering the kind of opportunity that experienced investors are always searching for. Each unit features 2 bedrooms and 1 full bath, providing a functional layout ready to be completely

  

  Tamika Marks

  Trademarks & Associates

  9737 S Prairie Ave, Chicago, IL 60628
• 

  

  /11

  $410,000

  • 6 Beds
  • 3 Baths

  8010 S Marshfield Ave, Chicago, IL 60620

  Absolutely turnkey investment or owner-occupied solid brick 3 flat /2 BEDROOMS EACH UNIT with unfinished basement. This property presents an excellent chance to invest in a well-maintained, move in ready multi-unit!! Huge apartments, hardwood floors throughout, living room, dining room, with decorative fireplace, enclosed back porch for extra storage with three car brick garage. The property is

  

  Brandice Hampton

  Baird & Warner

  8010 S Marshfield Ave, Chicago, IL 60620
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  /24

  $365,000

  $15K PRICE INCREASE

  • 3 Beds
  • 2 Baths

  10560 S Lafayette Ave, Chicago, IL 60628

  Don't miss this incredible opportunity to own a pristine, fully renovated 2-flat located in the heart of Chicago's South Side. Perfect for both investors and owner-occupants, this meticulously maintained property blends modern finishes with functional design, offering strong rental potential and long-term value. Each spacious unit boasts an open-concept living and dining area, ideal for

  

  Melanie Miller

  Keller Williams ONEChicago

  10560 S Lafayette Ave, Chicago, IL 60628
• 

  

  /10

  $299,900

  • 8 Beds
  • 4 Baths

  4504 S Paulina St, Chicago, IL 60609

  STRONG POSITIVE CASH FLOW IN THE HEART OF BACK OF THE YARDS Welcome to 4504 S Paulina St, a solid and well-maintained legal 3-unit building offering an excellent investment opportunity with positive cash flow. The property features three separate apartment units: First Floor Front Unit: Spacious apartment First Floor Rear Unit: Separate apartment Second Floor: Full-floor unit extending from front

  

  Jose Cortez

  Golden Enterprise Realty Inc

  4504 S Paulina St, Chicago, IL 60609
• 

  

  /22

  $195,000

  Pending

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

  5353 S Princeton Ave, Chicago, IL 60609

  Welcome to 5353 S Princeton Ave: this home offers comfort, character, and room to make it your own. Whether you're a first-time homebuyer, downsizing, or looking for your next investment, this property presents an excellent opportunity. Inside, you'll find a functional layout with comfortable living spaces, generous natural light, and an inviting feel. The lower level provides additional flexible

  

  Vikky Kaufman

  Coldwell Banker Realty

  5353 S Princeton Ave, Chicago, IL 60609
• 

  

  /30

  $349,000

  • 5 Beds
  • 2 Baths

  6420 S Evans Ave, Chicago, IL 60637

  Move-in ready 2-Flat in the heart of Woodlawn close to the new Obama Library. Live in one unit and rent out the other or use as an investment property. Both units ready for move-in. Lots of vintage charm still remains along with modern renovations. Fenced and gated front. Convenient street parking. This property offers a total of 5 bedrooms and 2 bathrooms. 3 bedrooms plus 1 bath up and 2

  

  Laraine Hanson

  Laraine Hanson

  6420 S Evans Ave, Chicago, IL 60637
• 

  

  /7

  $49,900

  • 4 Beds
  • 2 Baths
  • 1,424 Sq Ft

  7048 S Perry Ave, Chicago, IL 60621

  Experienced investors. Bring your vision to this two-story frame residence offers four bedrooms, two bathrooms. Convenient access to major transportation routes adds to the investment potential. Bring your contractor, complete your due diligence and explore the possibilities offered by this sizable lot. Drive-by access only at this time. Property sold strictly As-Is, Where-Is. Buyer responsible

  

  Reginald Patterson

  eXp Realty

  7048 S Perry Ave, Chicago, IL 60621
• 

  

  /12

  $849,000

  Pending

  • 14,841 Sq Ft

  5410 S Indiana Ave, Chicago, IL 60615

  Nestled in the heart of Chicago's rapidly growing Washington Park neighborhood, this fully occupied, six-unit building offers a blend of stable cash flow and exceptional future potential. Located near the University of Chicago and the expansive Washington Park, this property is positioned to benefit from the area's ongoing development, including the future Obama Presidential Center. With property

  

  Paul Frischer

  Berkshire Hathaway HomeServices Chicago

  5410 S Indiana Ave, Chicago, IL 60615
• 

  

  /43

  $385,000

  $15K PRICE DROP

  • 7 Beds
  • 3 Baths

  5219 S Peoria St, Chicago, IL 60609

  Great opportunity in Chicago's Back of the Yards neighborhood! This 2-unit property offers flexibility for both investors and owner-occupants. The first-floor unit features 3 bedrooms and 1 full bath and is currently tenant occupied, providing immediate rental income. The vacant second-floor unit also offers 3 bedrooms and 1 full bath, making it an excellent option to move in while collecting

  

  Elizabeth Goodchild

  Realty of America

  5219 S Peoria St, Chicago, IL 60609
• 

  

  /51

  $459,000

  Pending

  • 8 Beds
  • 3 Baths

  1542 S Drake Ave, Chicago, IL 60623

  Great opportunity to own a 3-unit property with investment or owner-occupant potential. The property offers flexibility for investors or buyers looking to live in one unit while generating rental income from the additional units. Located in a neighborhood with continued growth and potential. Sold As-Is where is.

  

  Brandice Hampton

  Baird & Warner

  1542 S Drake Ave, Chicago, IL 60623
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  /6

  $375,000

  $25K PRICE DROP

  • 7 Beds
  • 3 Baths

  8039 S Marquette Ave, Chicago, IL 60617

  Great investment opportunity at 8039 S Marquette! This solid 3-unit building offers strong income potential with each unit featuring its own separate heating system-an attractive benefit for both owners and tenants. The property includes three spacious units with functional layouts and ample natural light. While some updating is needed, this presents the perfect opportunity to add value and

  

  Tammy Jackson

  KM Realty Group, LLC

  8039 S Marquette Ave, Chicago, IL 60617
• 

  

  /13

  $399,999

  • 7 Beds
  • 2 Baths

  11025 S King Dr, Chicago, IL 60628

  Well-maintained 2-flat on historic King Drive offering the perfect opportunity to house hack or add a turnkey property to your investment portfolio. Unit 1 features 3 bedrooms, while Unit 2 offers 4 spacious bedrooms. With one unit becoming vacant soon, an owner-occupant can move in. The property features hardwood floors, ceramic-tiled kitchens and baths, fireplaces, individual heat and central

  

  Melanie Miller

  Keller Williams ONEChicago

  11025 S King Dr, Chicago, IL 60628
• 

  

  /25

  $349,900

  $10K PRICE DROP Pending

  • 4 Beds
  • 2 Baths

  8213 S Indiana Ave, Chicago, IL 60619

  A PRICE IMPROVEMENT JUST MADE THIS BRICK BEAUTY EVEN MORE ATTRACTIVE! New price and a renewed opportunity! Sometimes the right property circles back around-and this classic brick 2-unit in Chatham is making its encore appearance with even more reason to take another look. If you missed it before, this may be the opportunity you've been waiting for-but don't count on a third chance. Whether you're

  

  Tamika Marks

  Trademarks & Associates

  8213 S Indiana Ave, Chicago, IL 60619
• 

  /2

  $600,000

  • Land
  • 40,510 Sq Ft
  • $645,161 per Acre

  7016 S East End Ave, Chicago, IL 60649

  Exceptional development opportunity in the heart of South Shore. This expansive 40,453 SF parcel (250' x 163') is zoned RT-4 and offers outstanding potential for a luxury single-family residence, duplex development, or multi-unit residential project. Surrounded by mature trees and positioned on a beautiful residential block, the site is ideally located near the Obama Presidential Center, Lake

  

  Richard Lomax

  Fulton Grace Realty

  7016 S East End Ave, Chicago, IL 60649
• 

  

  /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
• 

  

  /40

  $799,000

  • 5 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  4104 N Richmond St, Chicago, IL 60618

  A 1910 Classic Reimagined with Scandinavian Style - East Irving Park **MOTIVATED SELLER RELOCATING.** Less than .2 miles from Horner Park and the Chicago River, this home pairs the character of a 1910 build with clean, Swedish-inspired updates. Vintage hardwood floors, light-filled rooms, and a pared-back aesthetic throughout three finished levels. There are plenty of flex options with this

  

  Elizabeth Goodchild

  Realty of America

  4104 N Richmond St, Chicago, IL 60618
• 

  

  /38

  $265,000

  • 6 Beds
  • 2 Baths

  6637 S Rhodes Ave, Chicago, IL 60637

  Woodlawn is a vibrant community with historical roots near Lake Michigan and the new Obama Center, featuring numerous new developments. This neighborhood is ideal for both new investments and your future home. Each unit includes 3 bedrooms, a living room, a dining room, and an eat-in kitchen. The enclosed porches provide additional storage space, and each unit is equipped with hookups for washers

  

  Otis Lazich

  Capital Investment Realty Group Inc

  6637 S Rhodes Ave, Chicago, IL 60637
• 

  

  /27

  $269,000

  $11K PRICE DROP

  • 6 Beds
  • 3 Baths

  7611 S Green St, Chicago, IL 60620

  Opportunity knocks in the heart of Auburn Gresham! Whether you're an investor looking to expand your portfolio or an owner-occupant ready to build long-term wealth, this solid brick 2-flat offers exceptional value at under $300,000. The spacious first-floor unit duplexes into the basement and features 3 bedrooms and 1 full bathrooms, and 1/2 bathroom providing the feel and functionality of a

  

  Melanie Miller

  Keller Williams ONEChicago

  7611 S Green St, Chicago, IL 60620
• 

  

  /34

  $550,000

  Pending

  • 6 Beds
  • 4 Baths

  6144 W School St, Chicago, IL 60634

  Multiple offers received, highest and best due by Sunday 10pm, seller to review the offers Monday morning and make a decision. Exceptional value and an outstanding investment opportunity! This well-maintained, solid 2-unit building with a finished in-law apartment offers generous living space, numerous major updates, and excellent income potential. The first-floor unit features approximately

  

  Kinga Korpacz

  Exit Realty Redefined

  6144 W School St, Chicago, IL 60634
• 

  

  /23

  $477,500

  $8K PRICE DROP

  • 9 Beds
  • 3 Baths

  6728 S Langley Ave, Chicago, IL 60637

  6728 S Langley Ave offers a rare blend of historic Chicago architecture and modern lifestyle potential. This stately three unit masonry residence stands with quiet confidence on a treelined West Woodlawn block. Inside, nearly 4,000 square feet of living space unfold across sun filled rooms, tall ceilings, and flexible layouts that invite both comfort and creativity. Each unit is thoughtfully

  

  Daisy Neal

  Daisy Neal

  6728 S Langley Ave, Chicago, IL 60637
• 

  

  /3

  $989,900

  New Construction

  • 9 Beds
  • 6 Baths

  3804 W Ohio St, Chicago, IL 60624

  COMING SOON - MID-SUMMER 2026 to West Humboldt Park! A fresh new chapter of modern Chicago living is arriving with this stunning, newly built 3-flat designed for comfort, style, and everyday ease. Each beautifully crafted residence offers 3 spacious bedrooms and 2 full baths, including a private primary suite designed to feel like your own personal retreat. Step inside and experience thoughtfully

  

  Edgar R. Guerrero

  REMAX Legends

  3804 W Ohio St, Chicago, IL 60624
• 

  

  /31

  $599,900

  • 9 Beds
  • 3 Baths

  2050 N Kenneth Ave, Chicago, IL 60639

  Incredible investment opportunity in Hermosa! Situated on an extra-wide lot, this legal 3-flat offers exceptional income potential with spacious units, recent renovations, and ample parking. The building features a 2-bedroom, 1-bath first-floor unit, a 3-bedroom, 1-bath second-floor unit, and a 4-bedroom, 1-bath third-floor unit. An additional finished attic with access from Unit 3 provides

  Matt Laricy Americorp, Ltd

  2050 N Kenneth Ave, Chicago, IL 60639
• 

  

  /38

  $589,000

  Pending

  • 5 Beds
  • 3 Baths

  6024 N Rockwell St, Chicago, IL 60659

  Excellent Investment or Owner-Occupant Opportunity in Chicago! This Well-Maintained Two-flat offers Two Spacious Residences plus a versatile In-law Garden Unit. The Main-Level Unit features a Large Living Room and Adjoining Family Room, Separate Dining Room, Updated Kitchen with Granite Counters, Tiled Backsplash and Stainless-Steel Appliances, Two Bedrooms, One Full Bathroom and an Entry Area

  Dominic Irpino IRPINO Real Estate, Inc.

  6024 N Rockwell St, Chicago, IL 60659
• 

  

  /36

  $520,000

  • 4 Beds
  • 2 Baths
  • 1,078 Sq Ft

  2945 N California Ave, Chicago, IL 60618

  This is your rare opportunity to own a distinctive 4-bedroom, 2-bath single-family home that's full of character, space, and endless potential. Location!! Don't overlook this hidden gem - Whether you're looking for a place to make your own or an investment with upside, this property offers the perfect canvas. Inside, you'll find a spacious and versatile floor plan filled with natural light,

  Joshua Irizarry Fulton Grace Realty

  2945 N California Ave, Chicago, IL 60618
• 

  

  /37

  $200,000

  Pending

  • 1 Bed
  • 1 Bath
  • 849 Sq Ft

  440 N Wabash Ave Unit 1008, Chicago, IL 60611

  *Multiple offers received*NEW PRICE! Attention Investors and Owner-Occupied Buyers! Welcome to Plaza 440, located at 440 N. Wabash Avenue in the heart of River North. This bright corner 1-bedroom condo, Unit 1008, features an abundance of north- and east-facing windows and is within walking distance of everything Chicago has to offer, including fine dining, grocery stores, shopping, coffee shops,

  Chih-Hao Yang Fulton Grace Realty

  440 N Wabash Ave Unit 1008, Chicago, IL 60611
• 

  

  /18

  $364,900

  Pending

  • 2 Beds
  • 2 Baths

  1430 N Maplewood Ave Unit 201, Chicago, IL 60622

  Welcome home to this sun-splashed, meticulously maintained gem in the heart of the Ukrainian Village. A residence that perfectly balances modern updates with the classic charm of its leafy surroundings. Step inside to a freshly painted interior that feels bright and airy from the moment you enter. The kitchen is ready for your next culinary adventure, featuring granite countertops and stainless

  Charles Lochotzki Compass

  1430 N Maplewood Ave Unit 201, Chicago, IL 60622
• 

  

  /22

  $750,000

  $50K PRICE DROP Pending

  • 5 Beds
  • 3 Baths

  Unlisted Address

  We cordially invite you to experience the entirety of this traditional brick North Center multi-unit building in 3D/virtual reality before seeing it in real life! Welcome home to this fantastic investment opportunity, located one block from Welles Park and just two blocks from Horner Park. Whether you're looking for a dog park, tennis courts, easy CTA bus/train transportation, grocery stores

  Maximilian Ortega Artizen Realty LLC

  Unlisted Address
• 

  

  /35

  $725,000

  $35K PRICE DROP Pending

  • 4 Beds
  • 3 Baths

  3445 N Monticello Ave, Chicago, IL 60618

  **Multiple offers received. Highest and best offer due by 5pm on Sunday, Sept. 13th****Hot investment opportunity in Avondale! Beautifully maintained and spacious 2-flat offering a fantastic opportunity for investors or owner-occupants looking to generate rental income. Both units feature the same desirable floor plan with expansive living and dining rooms, large kitchens with walk-in pantries,

  Sylwia Chliborob-Pawlak Redfin Corporation

  3445 N Monticello Ave, Chicago, IL 60618
• 

  

  /15

  $165,000

  Pending

  • 1 Bed
  • 1 Bath
  • 726 Sq Ft

  1937 W Pratt Blvd Unit 2N, Chicago, IL 60626

  Charming 1-bedroom, 1-bathroom unit that's truly move-in ready! Beautiful Brazilian cherry hardwood floors run throughout the entire home, and a parking space adds incredible value in this area. The unit has been freshly painted and features new appliances. Enjoy morning walks with your dog at Warren Park just across the street, or relax with your summer coffee on the spacious back deck. Whether

  Matt Laricy Americorp, Ltd

  1937 W Pratt Blvd Unit 2N, Chicago, IL 60626

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