Investment - Homes for Sale in Chicago, IL

• 

  

  

  /34

  $99,000

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  7141 S Woodlawn Ave, Chicago, IL 60619

  ***Investor Special - Prime South Shore Opportunity!*** Calling all investors, rehabbers, and visionaries! This 3-bed/1-bath brick single-family home with 2 floors, plus a basement, is a full-renovation project with outstanding upside in the rapidly growing South Shore neighborhood. Located just minutes from the University of Chicago campus, the Obama Presidential Library, Lake Michigan, Metra,

  Luminita Ispas Century 21 S.G.R., Inc.

  7141 S Woodlawn Ave, Chicago, IL 60619
• 

  

  

  /24

  $150,000

  • 2 Beds
  • 1 Bath

  9615 S Bensley Ave, Chicago, IL 60617

  Beautiful opportunity in a cozy corner of the South Deering Neighborhood and steps away from Bradley Park and 97th Street. This two story home sits on a well kept street with a driveway to its east on an oversized lot complimenting a 1.5 car, detached garage with ample space. The home has two, Upstairs Bedrooms allowing plenty of space on the main level and unfinished basement. With tall ceiling

  Luca Cannarile Compass

  9615 S Bensley Ave, Chicago, IL 60617
• 

  

  

  /18

  $295,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,233 Sq Ft

  6231 S Woodlawn Ave Unit 3N, Chicago, IL 60637

  Welcome to the heart of New Woodlawn! This spacious 3-bedroom, 2-bath condominium offers the perfect blend of comfort, style, and location in one of Chicago's most dynamic neighborhoods. Enjoy convenient access to the newly opened Obama Presidential Center, the University of Chicago, and the Woodlawn Central development just steps away. You'll also be surrounded by new residential developments

  Carlas Gilbert Prince Realty Group LLC

  6231 S Woodlawn Ave Unit 3N, Chicago, IL 60637
• 

  

  

  /39

  $1,500,000

  Pending

  • 10 Beds
  • 5 Baths

  3709 N Bosworth Ave, Chicago, IL 60613

  Situated on a premier, tree-lined street in the highly coveted Blaine School District. Exceptionally rare Lakeview multi-family investment asset presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage. Brick 2 flat with a non-conforming basement apartment and a 2-unit coach house in the rear.

  Matthew Mika Compass

  3709 N Bosworth Ave, Chicago, IL 60613
• 

  

  

  /21

  $494,900

  Pending

  • 9 Beds
  • 3 Baths

  4513 W West End Ave, Chicago, IL 60624

  Exceptional investment opportunity in the heart of Garfield Park! This oversized brick two-flat was completely gut renovated with permits in 2022, offering modern finishes, updated systems, and excellent income-producing potential. The property features three separate living spaces, each with its own gas and electric service. The first-floor unit offers 3 spacious bedrooms and 1 full bathroom.

  Sherita Owens Keller Williams ONEChicago

  4513 W West End Ave, Chicago, IL 60624
• 

  

  /24

  $274,900

  Pending

  • 5 Beds
  • 4 Baths

  5315 W Crystal St, Chicago, IL 60651

  5315 W Crystal St offers a strong value-add opportunity for an investor looking for a spacious brick multi-unit property with plenty of potential. This solid 2-flat features two large units, each consisting of 2 bedrooms, 1 full bathroom, generous living space, and additional sunroom areas located off the bedrooms. These sunrooms provide flexible extra space that could potentially be used as home

  Caden Wakim GenStone Realty

  5315 W Crystal St, Chicago, IL 60651
• 

  /2

  $574,900

  Pending

  • 10 Beds
  • 5 Baths

  2539 S Sawyer Ave, Chicago, IL 60623

  Incredible 4 unit investment opportunity in prime BUSTLING LITTLE VILLAGE- exceptionally well maintained condition- 3 unit building in front, along with a coach house unit in rear, including on-site laundry hookup for coin laundry opportunity in rear bldg. Both buildings have plenty of space in the clean, UNFINISHED Attics for potential ideas or projects. Each unit has their own water heater and

  Abraham Aguilera You Properties LLC

  2539 S Sawyer Ave, Chicago, IL 60623
• 

  /2

  $50,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,118 Sq Ft

  10724 S Langley Ave, Chicago, IL 60628

  Historic Row House Located In The Heart Of Beautiful Historic Pullman Neighborhood. This Property Consists Of Main Floor Living, Bedrooms, Bathrooms, And Full Basement. Ideal For Investors Or First Time Home Buyers Looking To Purchase In The Newly Revitalization Area. Property Sold AS-IS. Great Investment Opportunity!

  Renzie Gipson Coldwell Banker Realty

  10724 S Langley Ave, Chicago, IL 60628
• 

  

  /11

  $289,000

  $64K PRICE INCREASE

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft

  3338 N Oriole Ave, Chicago, IL 60634

  Welcome home to this beautifully laid-out ranch. The thoughtfully arranged interior offers an efficient and well-designed floor plan that maximizes every square foot. The inviting living room is accented by a fireplace, the separate dining room is perfect for those gatherings and entertaining, the functional kitchen has a galley style setting that comes in handy for all of your prepping and

  Sonia Zavala Chicagoland Brokers Inc.

  3338 N Oriole Ave, Chicago, IL 60634
• 

  

  /22

  $300,000

  Pending

  • 6 Beds
  • 2 Baths

  7037 S Washtenaw Ave, Chicago, IL 60629

  This classic Chicago-style two-flat offers a rare blend of vintage character and incredible versatility in the heart of the Marquette Park neighborhood. This brick beauty is a standout opportunity whether you are looking for a solid investment property or a spacious multi-generational living arrangement. Each of the two generous units features a functional three-bedroom, one-bathroom layout,

  Cirenio Jimenez Compass

  7037 S Washtenaw Ave, Chicago, IL 60629
• 

  

  /17

  $1,375,000

  Pending

  • 6,864 Sq Ft

  8649 W Foster Ave, Chicago, IL 60656

  Armchair investment. Extra clean & well-maintained brick building. All 6 units are 2-bedroom, 1.5-bath. The association is responsible for landscaping, parking, snow removal, and water. Most apartments are nicely updated and in great condition. Full basement has a laundry room with 2 washers & 2 dryers, a storage cage for each unit, and a large room that can be used for storage for extra income.

  Val Popovic Enterprise Realty Brokers Inc

  8649 W Foster Ave, Chicago, IL 60656
• 

  

  /12

  $599,000

  • Land
  • 16,988 Sq Ft
  • $1,535,897 per Acre

  4401 S Wabash Ave, Chicago, IL 60653

  Development opportunity in the heart of Bronzeville/Grand Boulevard in one of Chicago's most active and rapidly developing neighborhoods. Offering two contiguous vacant parcels totaling more than 17,200 SF on RT-4 Zoning. 4401-4409 S. Wabash Avenue is positioned within a strong growth corridor experiencing significant new residential and mixed-use development, this site presents an exceptional

  Kyle Capone Coldwell Banker Realty

  4401 S Wabash Ave, Chicago, IL 60653
• 

  

  /42

  $875,000

  • 6 Beds
  • 5 Baths

  3816 W Montrose Ave, Chicago, IL 60618

  This 3-unit property is fully rented and a great income-producing investment opportunity or perfect for a Live/Work owner! Lots of recent updates: the roof was replaced 2 years ago, the front windows of the 2-bedroom were replaced in 2025, and both the 2-bed and the coach house have new electrical. The 1600 Sq. Ft. storefront is currently operating as a catering/restaurant business and is on a

  Lora Vasileva Cedar Realty

  3816 W Montrose Ave, Chicago, IL 60618
• 

  

  /4

  $30,000

  • Land
  • 0 Sq Ft

  1212 N La Salle Dr Unit 344, Chicago, IL 60610

  MUST BE A UNIT OWNER AT 1212 N LASALLE TO PURCHASE. Prime Gold Coast/ Old Town location. This is an extra large and wide self parking spot that can accommodate a large SUV! On preferred level 3 which is indoors. This spot currently rents at $250/month. Garage is camera monitored 24/7. Easy self park access with fob. Ideal neighborhood. A great investment!

  Debra Flynn Baird & Warner

  1212 N La Salle Dr Unit 344, Chicago, IL 60610
• 

  

  /47

  $449,000

  • 6 Beds
  • 3 Baths

  7026 S Eberhart Ave, Chicago, IL 60637

  Beautifully updated two-unit building in Chicago's desirable Woodlawn neighborhood, offering an excellent opportunity for both investors and owner-occupants. This well-maintained property features spacious units, modern updates, and flexible living arrangements. The duplexed-down main-level unit offers 4 large bedrooms and 2 full baths, while the upper-level unit features 3 bedrooms and an

  Joan Couris Keller Williams Thrive

  7026 S Eberhart Ave, Chicago, IL 60637
• 

  

  /15

  $550,000

  • 4 Beds
  • 2 Baths

  1630 W Melrose St, Chicago, IL 60657

  Rare redevelopment or investment opportunity in the heart of Lakeview. Solid brick 2-flat featuring two 2-bedroom, 1-bath apartments with long-term tenants currently on month-to-month leases. Rents are below market, offering immediate upside potential for investors or future redevelopment. Property is zoned B1-3 and is being offered exclusively as part of a package sale with the adjacent property

  Robert Munds Jameson Sotheby's Intl Realty

  1630 W Melrose St, Chicago, IL 60657
• 

  

  /18

  $127,000

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  12910 S Green St, Chicago, IL 60643

  Great starter brick ranch home or investment property in the West Pullman area with detached 2 car garage. It is currently tenant occupied who is month to month. Home features hardwood floors throughout, an updated ceramic kitchen with stainless steel appliances, 1 full ceramic bath with two bedrooms. The roof was done within the last year, forced central heat, but no central air (an air

  Bahram Irani Baird & Warner

  12910 S Green St, Chicago, IL 60643
• 

  

  /12

  $849,900

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths

  1811 W Grand Ave, Chicago, IL 60622

  Located in the sought-after neighborhood of West Town and on a prime stretch of Grand Ave, this well-positioned 2-unit offers an excellent investment opportunity. The property combines timeless all brick construction with a desirable location and strong rental income potential. This property provides the opportunity for attractive cash flow, making it an ideal addition to an investor's portfolio

  Eleftheria Latka Delta Realty, Corp.

  1811 W Grand Ave, Chicago, IL 60622
• 

  /2

  $339,900

  • 7 Beds
  • 3 Baths

  7006 S Normal Blvd, Chicago, IL 60621

  Unlock the potential at 7006 S Normal Ave! This spacious multi-unit property presents an excellent opportunity for owner-occupants seeking the benefits of rental income or investors looking for their next value-add property. Featuring 7 total bedrooms and 3 full bathrooms, this property offers generous living space and plenty of potential. The kitchens and bathrooms were updated in 2025, and

  Lutalo McGee Ani Real Estate

  7006 S Normal Blvd, Chicago, IL 60621
• 

  

  /12

  $1,199,000

  • 3,960 Sq Ft

  460 W 28th Place, Chicago, IL 60616

  This well-maintained brick 6-unit building presents a compelling investment opportunity featuring a desirable unit mix of two (2) 2-bedroom / 2-bath apartments, two (2) 2 Bedroom/1 -Bath Units and two (2) 1-bedroom / 1-bath units. The property offers apartment-quality updates throughout, including modern kitchens and baths, stainless steel appliances, and contemporary range hoods that appeal to

  Angelo Labriola Sperry Van Ness

  460 W 28th Place, Chicago, IL 60616
• 

  

  /27

  $440,000

  Pending

  • 8 Beds
  • 4 Baths

  6923 S Sangamon St, Chicago, IL 60621

  Excellent investment opportunity! Well-maintained 4-unit building featuring four 2-bedroom, 1-bath units on a quiet residential block. Three units are currently occupied, including two Section 8 tenants and one market-rate tenant, providing immediate cash flow. One vacant unit offers the perfect opportunity for an owner-occupant or additional rental income. The occupied units include a stove and

  Frank Montro Keller Williams Preferred Rlty

  6923 S Sangamon St, Chicago, IL 60621
• 

  /2

  $21,500

  Pending Pre-Foreclosure

  • Land
  • 0 Sq Ft

  4004 W Grenshaw St, Chicago, IL 60624

  Don't miss out on the opportunity to own this prime piece of real estate, Zoned RT-4, located at 4004 West Grenshaw Street in Chicago, IL. This property is a vacant land/lot waiting for you to build your dream home or multi-unit investment property. With a lot size of 3,125 sq.ft., the possibilities are endless for what you can create on this spacious canvas. Don't wait to make your mark on this

  Jorge Romero Realty One Group Inc.

  4004 W Grenshaw St, Chicago, IL 60624
• 

  /2

  $230,000

  • 9 Beds
  • 3 Baths

  11932 S Eggleston Ave, Chicago, IL 60628

  Investor opportunity in a rapidly evolving Chicago market. This well-maintained 3-unit building, fully occupied, offers immediate income potential with long-term upside. Tenants in place provide stable cash flow, making this an ideal addition to any portfolio or a strong entry into multifamily investing. Please note: drive-by only at this time-do not disturb occupants. Located in an area

  Pamela Brown Baird & Warner

  11932 S Eggleston Ave, Chicago, IL 60628
• 

  

  /53

  $2,500,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 4,500 Sq Ft

  2424 N Burling St, Chicago, IL 60614

  Incredible opportunity for a 5 bedroom/4.5 bath home on picturesque Burling street. Home features hardwood flooring throughout, high ceilings, a newly renovated open concept kitchen/family room with custom cabinetry, Sub Zero and Wolf appliances, fridge drawers and large island. Family room leads to deck and additional garage rooftop deck for seamless entertaining. The sweeping open staircase

  Caroline Chambers Jameson Sotheby's Intl Realty

  2424 N Burling St, Chicago, IL 60614
• 

  

  /10

  $199,900

  $29K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  11916 S Stewart Ave, Chicago, IL 60628

  Stunning oversized home offering the perfect combination of space, comfort, and endless possibilities! This beautifully maintained property features 5 spacious bedrooms, 2 full bathrooms, and a fully finished basement designed for comfortable living and entertaining. Bright and inviting throughout, this home offers generous room sizes, abundant natural light, and a warm layout that instantly

  Eva Diaz ExaRealty LLC

  11916 S Stewart Ave, Chicago, IL 60628
• 

  

  /25

  $3,600,000

  • 18,216 Sq Ft

  1217 S Independence Blvd, Chicago, IL 60623

  Excellent investment opportunity to acquire a 36-unit multifamily property at 1217 S Independence Blvd as part of a 51-unit portfolio package with the companion 15-unit Flournoy property. Properties are being offered together as a package and are not intended to be sold separately. Independence is listed at $3,600,000 and Flournoy at $1,500,000, for a combined portfolio price of $5,100,000. The

  Brittany Hampton Exit Infinity Realty

  1217 S Independence Blvd, Chicago, IL 60623
• 

  

  /34

  $279,890

  • 6 Beds
  • 3 Baths
  • 3,928 Sq Ft

  2333 S Whipple St, Chicago, IL 60623

  Attention investors and savvy homeowners! This spacious 6-bedroom single-family home, located just north of Little Village, offers incredible potential and multiple flexible living areas. The main level features a generously sized living room, kitchen, three bedrooms, and a full bathroom. The finished attic offers a studio-style layout with a wet bar and bathroom, making it ideal for related

  Jose Aguilar Realty of America, LLC

  2333 S Whipple St, Chicago, IL 60623
• 

  

  /18

  $365,000

  • 6 Beds
  • 2 Baths

  530 N Lawler Ave, Chicago, IL 60644

  Don't miss this exceptional opportunity to own a versatile two-unit property with endless potential. Live in one unit while generating rental income from the other, or add this solid investment to your portfolio. The unfinished basement offers a blank canvas for your creative vision and the brand new garage adds even more value. Whether you're an owner-occupant or an investor, this property is

  Marcos Gonzalez eXp Realty

  530 N Lawler Ave, Chicago, IL 60644
• 

  

  /23

  $275,000

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths

  7707 S Peoria St, Chicago, IL 60620

  Exceptional investment opportunity in Chicago's Auburn Gresham neighborhood! This well-maintained brick two-unit building offers strong cash-flow potential with two long-term tenants currently in place on month-to-month leases, providing flexibility for investors and owner-occupants alike. The first-floor unit includes direct access to the basement, offering potential for a duplex-down

  Adrian Perez Avenue Properties Chicago

  7707 S Peoria St, Chicago, IL 60620
• 

  

  /29

  $390,000

  • 6 Beds
  • 2 Baths

  224 N Lockwood Ave, Chicago, IL 60644

  Excellent opportunity for owner occupied or investment! This well-maintained 2-flat building features currently occupied units, (no leases) where each unit offers spacious layouts and separate utilities. Make use of the additional space in the attic for expansion and the basement. Newer features/items: roofing, siding, fencing and windows (2022); Hot water tanks (2023) and furnaces. Ideal for

  Terry Umecker RE/MAX 10 in the Park

  224 N Lockwood Ave, Chicago, IL 60644
• 

  

  /3

  $695,000

  New Construction

  • 9 Beds
  • 6 Baths

  Chicago, IL 60620

  Simeon Manor Contemporary New Construction in West Chatham Owner-Occupant Buyers Only for one of four 3-unit residential buildings offering three spacious units, each featuring 3 bedrooms and 2 full bathrooms with open-concept layouts. Designed for modern living, each unit includes private outdoor deck space and high-quality finishes throughout. Kitchens feature stainless steel appliances,

  Lydel Blade Village Realty, Inc.

  Chicago, IL 60620
• 

  

  /8

  $380,000

  8807 S Cottage Grove Ave, Chicago, IL 60619

  INVESTOR OPPORTUNITY - 10-UNIT MULTIFAMILY | 88XX S. COTTAGE GROVE AVE., CHICAGO, IL Value-Add Multifamily Opportunity | 6 One-Bedrooms + 4 Two-Bedrooms Opportunity is knocking for investors looking to acquire a 10-unit multifamily property on Chicago's South Side. The building features an open-air, apartment-style layout consisting of six 1-bedroom/1-bath units and four 2-bedroom/1-bath units,

  Kurt Hudson ABS Property Consulting

  8807 S Cottage Grove Ave, Chicago, IL 60619
• 

  

  /44

  $819,900

  $20K PRICE DROP Pending

  • 6 Beds
  • 5 Baths

  5632 N Rockwell St, Chicago, IL 60659

  Exceptional investment and owner-occupant opportunity in the highly desirable Arcadia Terrace neighborhood! Situated on a quiet, tree- lined street, this meticulously maintained 2-flat, just steps from vibrant Lincoln Avenue, residents enjoy easy access to popular restaurants, cafes, shopping, and CTA transportation. This oversized building features two spacious units, making it an ideal

  Kevin Le Le Forever Realty, LLC

  5632 N Rockwell St, Chicago, IL 60659
• 

  

  /34

  $230,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,385 Sq Ft

  3809 W 86th St, Chicago, IL 60652

  Space, potential, and opportunity all come together in this home! Offering far more room than meets the eye, this home features a flexible floor plan with multiple living areas, a spacious kitchen, four bedrooms, two full bathrooms, and a full basement. The property does need repairs and updating, making it an excellent opportunity for a buyer with vision to bring out its full potential. Whether

  Toure Smith Red Pro Realty LLC

  3809 W 86th St, Chicago, IL 60652
• 

  

  /17

  $599,000

  • 8 Beds
  • 4 Baths

  118 N Menard Ave, Chicago, IL 60644

  Solid 4-Unit in Prime Austin Location! Each unit offers 2 bedrooms, 1 bathroom, hardwood floors, and a private basement-ideal for storage and laundry. Separate heating and water heaters for each unit. Tenants pay all utilities. Extra land in front allows for potential future parking expansion. Live in one unit and rent out the others-perfect for owner-occupants or investors. Strong rental market

  Shaheen Pervaiz Exit Strategy Realty

  118 N Menard Ave, Chicago, IL 60644
• 

  

  /23

  $199,000

  • 6 Beds
  • 2 Baths

  8012 S Elizabeth St, Chicago, IL 60620

  Opportunity awaits with this vacant brick 2-unit in Chicago's Historic Auburn Gresham neighborhood! Already taken down to the studs, this property is ready for its next chapter, allowing you to skip the demolition and begin bringing your vision to life. Major exterior improvements have already been completed, including a new roof and tuckpointing, providing a solid foundation for your renovation

  John Warren Forte Properties, Inc.

  8012 S Elizabeth St, Chicago, IL 60620
• 

  

  /26

  $45,000

  Pending

  • 4 Beds
  • 1.5 Baths
  • 1,475 Sq Ft

  6831 S Emerald Ave, Chicago, IL 60621

  INVESTMENT OPPORTUNITY, NEEDS FULL REHAB, INVESTORS BRING YOUR IDEA'S!!! 4 BEDROOM, 1.1 BATH WITH HARDWOOD FLOORS, GREAT LAYOUT, FULL UNFINISHED BASEMENT, NICE BACKYARD & 2 CAR GARAGE, PROPERTY SOLD "AS IS"

  Steve Olszewski Berkshire Hathaway HomeServices Starck Real Estate

  6831 S Emerald Ave, Chicago, IL 60621
• 

  /2

  $100,000

  • Land
  • 0 Sq Ft

  6625 S Ellis Ave, Chicago, IL 60637

  Attention Developers | 6625 S Ellis Ave | 25x125 Lot | RT-4 Zoning | Woodlawn Proper Positioned in Woodlawn proper, this 25x125 RT-4 parcel offers a compelling construction opportunity in one of Chicago's most strategically evolving neighborhoods. With multi-unit zoning already in place, the site is ideal for contemporary multi-family housing, modern townhomes, or a design-forward rental asset

  Jennifer Bell Fulton Grace Realty

  6625 S Ellis Ave, Chicago, IL 60637
• 

  

  /55

  $455,000

  • 8 Beds
  • 3 Baths

  1419 S Kedvale Ave, Chicago, IL 60623

  Outstanding investment opportunity! This legal 3-unit building offers 8 total bedrooms and 3 full bathrooms, making it an excellent addition to any investment portfolio or the perfect opportunity for an owner-occupant. Live in one unit while generating rental income from the others, or maximize your returns by leasing all three units. Featuring functional floor plans, excellent income potential,

  Rocio Rodriguez Solaris Enterprises Inc

  1419 S Kedvale Ave, Chicago, IL 60623
• 

  

  /21

  $159,900

  $18K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  6938 S Dorchester Ave Unit 2, Chicago, IL 60637

  Welcome home to this spacious 2-bedroom, 2-bath condo in the heart of South Shore! Offering approximately 1,350 square feet of living space, this second-floor residence features hardwood floors, a cozy gas fireplace, and an open-concept layout that's perfect for both everyday living and entertaining. The kitchen is equipped with granite countertops, stainless steel appliances, and plenty of

  Emiko Pope Keller Williams Preferred Realty

  6938 S Dorchester Ave Unit 2, Chicago, IL 60637

Showing Results 121 - 160, Page 4 of 18