Investment - Homes for Sale in Chicago, IL

• 

  

  

  /24

  $710,000

  Pending

  • 11 Beds
  • 6 Baths

  4326 S Calumet Ave, Chicago, IL 60653

  Stunning, fully gut-rehabbed 3-unit building in Bronzeville offering the perfect blend of modern updates and timeless appeal. Situated on a quiet cul-de-sac next to a beautifully maintained park, this property provides a peaceful setting just steps from Bronzeville's growing shopping and dining scene. Each spacious unit features a stylish kitchen with shaker cabinetry, granite countertops, two

  Alexandre Stoykov Compass

  4326 S Calumet Ave, Chicago, IL 60653
• 

  

  

  /20

  $319,000

  • 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
• 

  

  

  /9

  $134,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  6206 N Francisco Ave Unit 2B, Chicago, IL 60659

  Charming 1-bedroom, 1-bath condo in the highly sought-after West Ridge neighborhood! Featuring granite countertops, stainless steel appliances, new electricals, and brand-new windows. Whether you're looking to move right in or add a solid investment to your portfolio, this property is an excellent choice. Enjoy convenient on-site amenities including coin laundry along with a spacious,

  Maggie Perez HomeSmart Connect LLC

  6206 N Francisco Ave Unit 2B, Chicago, IL 60659
• 

  

  

  /14

  $99,750

  • 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
• 

  

  

  /21

  $125,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,450 Sq Ft

  6536 S Rhodes Ave, Chicago, IL 60637

  Excellent Investment or Owner-Occupant Opportunity in Woodlawn! Well-priced 2 bed / 1.5 bath classic Chicago Bungalow on a 3,660 sq ft lot. This home features a timeless stone facade, original details, and solid structure-perfect for renovation. Unfinished attic with stair access offers potential for a large primary suite. Full unfinished basement with half bath adds opportunity to expand living

  Denise Foote Baird & Warner

  6536 S Rhodes Ave, Chicago, IL 60637
• 

  

  /22

  $775,000

  • 5 Beds
  • 2 Baths

  1831 N California Ave, Chicago, IL 60647

  Experience the best of Logan Square with this turnkey two-unit gem, perfectly positioned just a houses from the 606 Trail entry. Whether you're looking for a savvy live-in investment or a high-performing addition to your portfolio, this duplex delivers on every front. Both the 3BR/1BA and 2BR/1BA units have been freshly reimagined with crisp paint, brand-new cabinetry, and sleek new appliances.

  Richard Kasper Compass

  1831 N California Ave, Chicago, IL 60647
• 

  

  /13

  $105,000

  $15K PRICE DROP

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

  8112 S Escanaba Ave, Chicago, IL 60617

  Smart Investment or Ideal Starter Home! Currently Rented and Cashflowing 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
• 

  

  /48

  $710,000

  • 11 Beds
  • 5 Baths

  3651 S Wood St, Chicago, IL 60609

  One-of-a-kind, massive all-brick 3-flat-this is the kind of building that rarely hits the market, especially in such impeccable condition. From the moment you see it, you can tell it's been exceptionally well maintained and thoughtfully upgraded, making it a true standout for both savvy investors and owner-occupants ready to build long-term wealth. This oversized property offers all new windows,

  Claudia Hernandez RE/MAX Mi Casa

  3651 S Wood St, Chicago, IL 60609
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  /6

  $210,000

  $12K PRICE DROP

  • 7 Beds
  • 5 Baths

  864 E 87th Place, Chicago, IL 60619

  ** Prime 2-Unit Investment Opportunity - Oversized Lot! ** Welcome to 864 E 87th Place - a fantastic income-generating property situated on an **oversized lot** offering both space and strong rental potential! This 2-unit building with a duplexed second floor is ideal for investors or owner-occupants seeking to maximize returns. **Property Highlights:** * **Unit 1 (1st Floor):** 3 bedrooms, 2

  Terina Fountain Coldwell Banker Realty

  864 E 87th Place, Chicago, IL 60619
• 

  

  /12

  $110,000

  Pending

  • 2 Beds
  • 1 Bath
  • 836 Sq Ft

  1629 S Karlov Ave, Chicago, IL 60623

  GREAT INVESTMENT OPPORTUNITY- SOLID BONES, SPACIOUS 2 BEDROOM 1 BATH, FULL BASEMENT. JUST WAITING FOR YOUR TOUCHES. DO NOT MISS THIS ONE! AS-IS

  Tami Sparks Better Homes & Gardens Real Estate

  1629 S Karlov Ave, Chicago, IL 60623
• 

  

  /8

  $140,000

  Pending

  • 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
• 

  /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
• 

  

  /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
• 

  

  /24

  $479,900

  Pending

  • 4 Beds
  • 2 Baths

  10542 S Artesian Ave, Chicago, IL 60655

  BEAUTIFUL INVESTMENT PROPERTY - IMPECCABLY MAINTAINED - BRICK 2-FLAT IN WEST BEVERLY. SPACIOUS UNITS - BOTH 2 BEDROOM/1 BATH WITH FORMAL DINING ROOMS, HARDWOOD FLOORS, AND CENTRAL AC. ELECTRIC AND GAS SEPARATELY METERED AND PAID BY TENANTS. RECENT UPDATES INCLUDE ROOF (2016) FURNACES (2016) AC CONDENSERS (2016) WINDOWS (2017) HOT-WATER TANK (2024). STEPS FROM RESTAURANTS - BARS - SHOPPING - AND

  Robert Fleckenstein First In Realty, Inc.

  10542 S Artesian Ave, Chicago, IL 60655
• 

  /2

  $925,000

  Pending

  3101 N Natoma Ave, Chicago, IL 60634

  Great investment opportunity awaits. Rarely available building in great condition and location. Surrounded by single family homes. Roof 2014, deck/patio 2021, updated copper plumbing and electric wires, fully occupied with strong rental history. Large apartments include 5 units/4 rooms-1 bedroom and 2 large studios are with separate central heat and AC (studio tenants pay all utilities). 3 car

  Sarah Leonard Legacy Properties, A Sarah Leonard Company, LLC

  3101 N Natoma Ave, Chicago, IL 60634
• 

  

  /16

  $215,000

  Pending

  • 5 Beds
  • 2 Baths

  14010 S Green Bay Ave, Chicago, IL 60633

  Welcome to 14010 S Greenbay Ave, a solid and income-producing 2-unit property offering flexibility, strong rental potential, and long-term upside-perfect for both savvy investors and owner-occupants looking to offset their mortgage. Each unit features a spacious and functional layout with generously sized living areas, ample natural light, and well-proportioned bedrooms. The property is designed

  Michael Woloszczuk Avenue Properties Chicago

  14010 S Green Bay Ave, Chicago, IL 60633
• 

  

  /29

  $325,000

  $20K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 803 Sq Ft

  1455 N Sandburg Terrace Unit 504B, Chicago, IL 60610

  Welcome to your perfect city condo at 1455 N Sandburg Terrace #504. A beautifully maintained 2-bed, 1-bath home in the heart of Old Town. This exceptional property features a bright, east facing layout with sweeping city views! You'll also find an updated kitchen with stainless steel appliances, generous closet space throughout, an updated bathroom with walk in shower, and an oversized primary

  Jacqueline Duckett Compass

  1455 N Sandburg Terrace Unit 504B, Chicago, IL 60610
• 

  

  /27

  $400,000

  Pending

  • 8 Beds
  • 4 Baths

  2233 S Trumbull Ave, Chicago, IL 60623

  **Prime 4-unit apartment investment in Little Village** This solid 2-story building in Little Village is a powerhouse for any real estate portfolio. Unlike many properties in the area, this building features 4 full apartment units all located on the 1st and 2nd floors, offering premium above-grade living for every tenant. Unit highlights: Uniform layouts: 4 units feature a consistent 2-bedroom,

  Patricia Arboleda Century 21 S.G.R., Inc.

  2233 S Trumbull Ave, Chicago, IL 60623
• 

  

  /92

  $719,000

  Pending

  • 8 Beds
  • 4 Baths

  5433 W Melrose St, Chicago, IL 60641

  BELMONT CRAGIN / PORTAGE PARK! Legal 2-flat with a nonconforming garden apartment and a 2-car detached garage. Excellent investment opportunity in the desirable Belmont Cragin/Portage Park neighborhood. This attractive 21/2-story brick building also offers the potential for one additional outdoor parking space. The property features approximately 2,800 square feet of above-grade living area, with

  Victor Lopez Coldwell Banker Realty

  5433 W Melrose St, Chicago, IL 60641
• 

  

  /50

  $700,000

  • 6 Beds
  • 3 Baths

  6066 N Albany Ave, Chicago, IL 60659

  Rare opportunity to own a beautifully updated solid brick 3-flat in the highly sought-after West Ridge neighborhood. This well-maintained income-producing property has been extensively renovated and offers the perfect combination of strong cash flow potential and long-term appreciation. Each unit is equipped with its own separate central HVAC system, providing comfort and convenience for tenants

  Long Nguyen Real People Realty

  6066 N Albany Ave, Chicago, IL 60659
• 

  

  /11

  $2,415,000

  4150 S Western Ave, Chicago, IL 60609

  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 neighborhoods. Each unit has separate PIN number! The first-floor commercial spaces are not included in the sale but may be acquired as a package

  Jim Mantas The Leading Realtors Corp.

  4150 S Western Ave, Chicago, IL 60609
• 

  

  /42

  $1,350,000

  Pending Pre-Foreclosure

  • 13 Beds
  • 8 Baths

  4541 S Forrestville Ave, Chicago, IL 60653

  RARE investment opportunity in the heart of Bronzeville - a beautifully restored 1903 historic mansion converted into four oversized luxury apartments on a rare double-wide lot. This architect-designed 2025 renovation blends timeless vintage character with modern functionality, preserving original stained and leaded glass, intricate woodwork, hardwood floors, pocket doors, fireplaces, built-ins,

  Michael Scanlon eXp Realty

  4541 S Forrestville Ave, Chicago, IL 60653
• 

  

  /36

  $520,000

  • 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
• 

  /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
• 

  

  /24

  $595,000

  • 3,952 Sq Ft

  8624 S Maryland Ave, Chicago, IL 60619

  Exceptional investment opportunity! This well-maintained 6 unit multi-family property offers a total of 10 bedrooms and 6 bathrooms, making it ideal for both long term and short term rental strategies. Each unit features its own kitchen, living room, and dining area, offering comfortable, fully independent living spaces for tenants or guests. The property is equipped with a 24 hour security

  Harry Ventimiglia Keller Williams Preferred Rlty

  8624 S Maryland Ave, Chicago, IL 60619
• 

  

  /27

  $239,000

  $10K PRICE DROP

  • 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
• 

  /2

  $25,000

  $20K PRICE DROP

  • Land
  • 0 Sq Ft

  8415 S Mackinaw Ave, Chicago, IL 60617

  This lot is ready for you to build your own investment for your future. It comes quicker than you may think. Start now!

  Catherine O'Shea O'Shea Realty, LLC

  8415 S Mackinaw Ave, 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
• 

  

  /18

  $123,000

  • Studio
  • 1 Bath
  • 600 Sq Ft

  6700 S South Shore Dr Unit 18K, Chicago, IL 60649

  Prime 18th-Floor Lakefront Studio with Alcove & Included Garage Parking - Unbeatable Views! Experience true Chicago lakefront living from the 18th floor of the iconic 6700 S South Shore Drive. This bright, updated studio delivers jaw-dropping panoramic Lake Michigan and skyline views through expansive floor-to-ceiling windows that fill the space with natural light and ever-changing scenery. The

  Elyahu Herszberg Kale Realty

  6700 S South Shore Dr Unit 18K, Chicago, IL 60649
• 

  

  /10

  $100,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 714 Sq Ft

  6415 S Eberhart Ave, Chicago, IL 60637

  Excellent investment opportunity in the rapidly appreciating Woodlawn neighborhood. This 3-bedroom frame home is currently occupied with market-rate tenants paying $1,000 per month, Easy show making this a straightforward transition for an investor. The property is priced well under market value, offering substantial upside for a buyer willing to apply a little administrative and property

  Damaris Santiago Manage Chicago, Inc.

  6415 S Eberhart Ave, Chicago, IL 60637
• 

  /2

  $180,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths

  4937 S Hoyne Ave, Chicago, IL 60609

  Great investment opportunity! Check out this 2-unit building located at 4937 S Hoyne Ave in Chicago. The property is in need of TLC and repairs and is being sold strictly as-is. Each unit offers a functional layout with a living room, 2 bedrooms, a full bathroom, and a kitchen. The property also features a yard and a 2-car garage.

  Luis Ortiz RE/MAX Partners

  4937 S Hoyne Ave, Chicago, IL 60609
• 

  

  /35

  $350,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  1255 S State St Unit 1302, Chicago, IL 60605

  1255 S State St #1302 | South Loop Skyline Living This is the one you've been waiting for. Positioned in the highly coveted "02" tier, this rarely available 2-bedroom, 2-bathroom split floor plan offers the perfect blend of sophisticated city living and a front-row seat to Chicago's evolving landscape. The Interior Experience Step into a bright, open-concept space defined by panoramic northwest

  Paula Calzolari Berkshire Hathaway HomeServices Starck Real Estate

  1255 S State St Unit 1302, Chicago, IL 60605
• 

  

  /41

  $1,225,000

  Pending

  • 3 Beds
  • 3.5 Baths

  610 N Damen Ave, Chicago, IL 60622

  Welcome to 610 N Damen, a beautifully updated 3-bedroom, 3.1-bath single-family home offering exceptional indoor-outdoor living in the heart of Ukrainian Village. Thoughtfully reimagined since its last sale, this home showcases extensive upgrades, including a complete exterior transformation with Magnolia Collection Hardie siding, new Pella windows, privacy fencing, and professional landscaping.

  Lauren Mitrick Wood Compass

  610 N Damen Ave, Chicago, IL 60622
• 

  

  /10

  $70,000

  Open Sat 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  7337 S South Shore Dr Unit 326, Chicago, IL 60649

  Welcome to this beautifully updated 1-bedroom, 1-bathroom condo in the desirable Lake Terrace waterfront building, located in Chicago's historic South Shore neighborhood. Enjoy an exceptional combination of comfort, convenience, and value with an impressive array of building amenities, including 24-hour security and door service, multiple elevators, private storage, a fitness center, onsite

  Precious Credit Coldwell Banker Realty

  7337 S South Shore Dr Unit 326, Chicago, IL 60649
• 

  

  /12

  $1,550,000

  Pending

  • 6,204 Sq Ft

  1344 W 19th St, Chicago, IL 60608

  This well-maintained 7-unit brick apartment building presents an excellent investment opportunity in Chicago's Pilsen neighborhood. The property features a desirable and diversified unit mix consisting of one (1) 3 Bed / 2 Bath unit, two (2) 2 Bed / 1 Bath units, and four (4) 1 Bed / 1 Bath units, appealing to a broad tenant base ranging from young professionals to small families. The units have

  Angelo Labriola Sperry Van Ness

  1344 W 19th St, Chicago, IL 60608
• 

  

  /20

  $219,900

  $10K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft

  6651 S Maryland Ave Unit 1E, Chicago, IL 60637

  Welcome home to this awesome 2-bedroom, 2-bath duplex-up condo in the heart of Woodlawn. This home features hardwood floors throughout the main level, an open layout, and exposed brick that adds character and warmth. The primary suite includes an ensuite bathroom, offering comfort and privacy. Kitchen features stainless steel refrigerator and other appliances will be upgraded to stainless steel

  Sheree Bradley Kale Realty

  6651 S Maryland Ave Unit 1E, Chicago, IL 60637
• 

  /2

  $8,000

  Pending

  • Land
  • 0 Sq Ft

  5958 S Ada St, Chicago, IL 60636

  Development Opportunity in West Englewood! This 30.6x124.5 corner lot is zoned RS-3, allowing for a single family or 2 flat property. 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

  Ronald Ohr Avenue 1 Realty Group

  5958 S Ada St, Chicago, IL 60636
• 

  

  /26

  $300,000

  $25K PRICE DROP Pending

  • 1 Bed
  • 1 Bath
  • 860 Sq Ft

  200 N Dearborn St Unit 4407, Chicago, IL 60601

  Sky-High Sophistication on the 44th Floor. Discover a rare opportunity to own one of the most desirable corner residences in the heart of downtown Chicago. Soaring high above the city on the 44th floor, this spacious 1-bedroom, 1-bath home offers an exceptional combination of luxury, light, and breathtaking views. Step inside to an open-concept living and dining area framed by floor-to-ceiling

  Alexander Tzallas RE/MAX 10 Lincoln Park

  200 N Dearborn St Unit 4407, Chicago, IL 60601
• 

  

  /17

  $959,000

  $30K PRICE DROP Pending

  • 6,716 Sq Ft

  5007 W Diversey Ave, Chicago, IL 60639

  Price Reduced - Turnkey 6-Unit Investment Opportunity Turnkey 6-unit investment opportunity in the highly desirable Belmont Cragin neighborhood. This well-maintained 1970s yellow brick building features a strong unit mix of five 2-bedroom, 1-bath units and one 1-bedroom, 1-bath unit, all above grade with spacious layouts and eat-in kitchens. Many units have been updated over time, reflecting

  Randy Ghanayem Coldwell Banker Real Estate Group

  5007 W Diversey Ave, Chicago, IL 60639
• 

  

  /46

  $550,000

  Pending

  • 6 Beds
  • 2 Baths

  4862 W Cortland St, Chicago, IL 60639

  Exceptional investment opportunity in the heart of Chicago's desirable Cragin neighborhood! This spacious multi-family property offers approximately 2,540 sq ft of living space on a generous 6,300 sq ft lot, making it ideal for both investors and owner-occupants. Featuring 6 bedrooms and 2 bathrooms, this classic building provides ample space for rental income, multi-generational living, or a

  Alfredo Gonzalez Compass

  4862 W Cortland St, Chicago, IL 60639

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