Investment - Homes for Sale in Chicago, IL

• 

  

  

  /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
• 

  

  

  /22

  $599,000

  Pending

  • 7 Beds
  • 3 Baths

  6525 W Belmont Ave, Chicago, IL 60634

  A must-see solid brick muli-unit building on a corner lot! Also includes a rare three-car garage with storage above. This is a great opportunity to live in one unit and rent the rest of the building. No leases currently are in place rents are projected. All units are separately metered. Located in prime rental market, this investment has an abundance of classic charm. First and second floor units

  Lucas Winter First In Realty, Inc.

  6525 W Belmont Ave, Chicago, IL 60634
• 

  

  

  /53

  $850,000

  Pending

  • 7 Beds
  • 5 Baths

  3806 W Armitage Ave, Chicago, IL 60647

  Attention owner-occupants or investors. Duplex up will be available June 2026. This exceptional two-unit property in the heart of Logan Square represents a Perfect owner-occupancy with rental or premier investment opportunity with both units currently leased and producing income. Entirely rehabbed from the studs in 2019, the residence showcases high-end craftsmanship and gleaming hardwood

  Stephanie Miller Redfin Corporation

  3806 W Armitage Ave, Chicago, IL 60647
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  /37

  $950,000

  • 9 Beds
  • 5 Baths

  2622 N Central Park Ave, Chicago, IL 60647

  Fully Renovated Logan Square 2-Flat - Exceptional Investment or Owner-Occupant Opportunity. Be the first to see this beautifully renovated 2-flat in the heart of Logan Square, offering incredible flexibility for investors and owner-occupants alike. The second-floor unit is a spacious duplex-up featuring 4 bedrooms and 2 full bathrooms, completely updated with new stainless steel appliances,

  Steve Dombar Redfin Corporation

  2622 N Central Park Ave, Chicago, IL 60647
• 

  

  /36

  $444,000

  $9K PRICE INCREASE Pending

  • 5 Beds
  • 4 Baths

  5011 S Kilbourn Ave, Chicago, IL 60632

  Exceptional investment opportunity in the heart of Chicago! This well-maintained all-brick two-unit building offers an ideal combination of owner-occupant potential and strong rental income. Rehabilitated in 2024, the property features two spacious units with a total of five bedrooms and four full bathrooms, providing versatile living arrangements for a variety of buyers. The recently remodeled

  Kimberly Brown-Lewis Redfin Corporation

  5011 S Kilbourn Ave, Chicago, IL 60632
• 

  

  /43

  $960,000

  $25K PRICE DROP

  • 6 Beds
  • 4 Baths

  2432 N Campbell Ave, Chicago, IL 60647

  Rare Logan Square Investment Opportunity with Coach House! Located on a charming, tree-lined block in the heart of Logan Square, 2432 N. Campbell Ave offers a unique opportunity to own a multifamily property with tremendous potential. The property features a well-maintained frame two flat accompanied by a tri-level coach house, creating a flexible setup for investors, owner-occupants, or buyers

  Brianna Schmidt Second City Real Estate

  2432 N Campbell Ave, Chicago, IL 60647
• 

  

  /35

  $339,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  135 N Lotus Ave, Chicago, IL 60644

  NEW TO MARKET! Welcome to 135 N Lotus Ave, a spacious brick single-family home offering a great combination of size, functionality, and potential in Chicago's Austin neighborhood. This 3-bedroom, 2-bath home features approximately 1,200 square feet of living space, providing plenty of room for comfortable everyday living. The home sits on a generous 25 x 125 lot and offers a full finished

  Maria Gutierrez Golden City Realty, Inc.

  135 N Lotus Ave, Chicago, IL 60644
• 

  

  /44

  $1,300,000

  • 10 Beds
  • 5 Baths

  4749 N Dover St, Chicago, IL 60640

  Rarely available and meticulously maintained, this turn-key Sheridan Park gem offers an unmatched investment opportunity for savvy buyers and portfolio collectors alike. This premier estate showcases an exceptional pride of ownership, featuring a classic, solid brick 2-flat, a fully finished walk-out garden unit, and a spectacular, detached multi-level brick coach house. Generating four distinct

  Veronica Rodriguez Redfin Corporation

  4749 N Dover St, Chicago, IL 60640
• 

  

  /44

  $599,000

  $25K PRICE DROP

  • 5 Beds
  • 3 Baths

  5105 W School St, Chicago, IL 60641

  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, Separate Dining Room, Eat-in Kitchen, Primary Bedroom, Secondary Bedroom with Adjoining Sitting Room / Office, One Full Bathroom and an Entry Area with Stairs that lead to the One Bedroom,

  Dominic Irpino IRPINO Real Estate, Inc.

  5105 W School St, Chicago, IL 60641
• 

  

  /18

  $269,900

  • 1 Bed
  • 1 Bath
  • 1,080 Sq Ft

  260 E Chestnut St Unit 2505, Chicago, IL 60611

  Move right into this beautifully maintained one bedroom in an unbeatable location. This home offers a clean, functional layout with great natural light and a comfortable living space that's easy to make your own. Truly move in ready, making it a perfect option for a primary residence, in town, or investment. Located just steps from everything Streeterville has to offer, you're surrounded by top

  Jacob Reiner Redfin Corporation

  260 E Chestnut St Unit 2505, Chicago, IL 60611
• 

  

  /33

  $499,900

  • 6 Beds
  • 3 Baths

  2019 N Leclaire Ave, Chicago, IL 60639

  Great opportunity for investment or owner occupancy - This two flat with a basement in-law unit features two spacious two bedroom, one bath units. The first and second floor units have identical layouts with a light filled living room featuring a brick fireplace that flows in to the separate dining room, spacious kitchen, two bedrooms, and full bathroom. The finished basement offers a living

  Marina Collazo Redfin Corporation

  2019 N Leclaire Ave, Chicago, IL 60639
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  /49

  $1,100,000

  • 5 Beds
  • 4 Baths

  1219 N Damen Ave, Chicago, IL 60622

  Rarely available all-brick 2-unit building in an unbeatable Wicker Park location, just steps from Colectivo Coffee! Situated on a 24' x 120' lot, this property offers more than 1,300 SF per floor, good bones, vintage curb appeal, generous ceiling heights, excellent outdoor space, and a highly desirable layout. Zoned RT-4 and not located in a landmark district. The tenant occupied top-floor

  Nicholaos Voutsinas Redfin Corporation

  1219 N Damen Ave, Chicago, IL 60622
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  /42

  $250,222

  • 5 Beds
  • 3 Baths

  7949 S Marquette Ave, Chicago, IL 60617

  INVESTORS, THIS ONE DESERVES YOUR ATTENTION! Brick 3-unit building offering multiple income streams under one roof. The garden unit features 1 bedroom and 1 bath, while the two additional units each offer 2 bedrooms and 1 bath. All units have been recently updated and feature attractive wood flooring. Whether you're looking to expand your rental portfolio, generate additional rental income, or

  Jaime Birks Realty of America

  7949 S Marquette Ave, Chicago, IL 60617
• 

  

  /29

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  1626 W Greenleaf Ave Unit 1E, Chicago, IL 60626

  Welcome to 1626 W Greenleaf Ave, Unit 1E - a fantastic opportunity to own a spacious 3-bedroom, 1.1-bath home in a desirable and convenient location. This well-positioned property offers a comfortable floor plan with generously sized living spaces and three bedrooms, providing plenty of room for everyday living, guests, a home office, or additional flexibility. Enjoy the convenience of being

  Maria Gutierrez Golden City Realty, Inc.

  1626 W Greenleaf Ave Unit 1E, Chicago, IL 60626
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  /27

  $450,000

  Pending

  • 5 Beds
  • 2 Baths

  2835 W Wellington Ave Unit 2, Chicago, IL 60618

  Welcome to 2835 W Wellington, a stunning top-floor duplex up with a spacious, light-filled 5-bedroom, 2-bath condo. This square footage and flexibility are incredibly rare to find. Previously operated as a successful Air BnB, the unit has been designed for comfortable living at every turn, and furniture is available for purchase, making this a truly turnkey investment opportunity. The heart of

  Kenneth Sabino Baird & Warner

  2835 W Wellington Ave Unit 2, Chicago, IL 60618
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  /30

  $245,000

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

  738 S Kedzie Ave Unit 2, Chicago, IL 60612

  Welcome to 738 S Kedzie Ave, Unit 2! This beautiful 3-bedroom, 2-full-bath duplex-up condo offers spacious living, modern comfort, and a layout designed for both everyday living and entertaining. Enjoy generous living spaces across two levels, well-sized bedrooms, two full baths, and the added convenience of garage parking. One of the home's standout features is rooftop access-perfect for

  Tameka McClellon Tameka McClellon

  738 S Kedzie Ave Unit 2, Chicago, IL 60612
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  /14

  $625,000

  Pending

  • 8 Beds
  • 2 Baths

  823 S Carpenter St, Chicago, IL 60607

  Brookline Real Estate is pleased to present 823 S. Carpenter Street, a fully leased two-unit investment property in Chicago's Little Italy/University Village neighborhood. The property contains two four-bedroom, one-bath apartments and totals approximately 2,656 square feet. Located within the UIC campus and near the Illinois Medical District, Taylor Street, public transportation and downtown

  William Lundy Brookline Real Estate LLC

  823 S Carpenter St, Chicago, IL 60607
• 

  

  /16

  $79,900

  Pending

  • 5 Beds
  • 2 Baths
  • 882 Sq Ft

  8332 S Kerfoot Ave, Chicago, IL 60620

  Exceptional Investment Opportunity in Auburn Gresham Priced at just $79,900-approximately $91 per square foot-this 5-bedroom, 2-bathroom home at 8332 S. Kerfoot Avenue offers outstanding value and exciting possibilities in Chicago's Auburn Gresham neighborhood. Offered in as-is condition, the property provides a fantastic opportunity for investors or buyers ready to renovate and bring their

  Jessica Macey Real Broker LLC

  8332 S Kerfoot Ave, Chicago, IL 60620
• 

  

  /23

  $1,400,000

  Pending

  5444 W Huron St, Chicago, IL 60644

  Are you in the market for a turn key arm chair investment....look no further. This is a solid brick 12-Unit in the heart of North Austin, that is vastly appreciating, while generating 174,000 per year with room for rent increases. Common areas and units are in great condition, consisting of 3-2br and 9-1br units with hardwood flooring, separate living/dining room, separate furnaces. Most unit are

  Aziz Abdelmajeid Inter Properties Inc

  5444 W Huron St, Chicago, IL 60644
• 

  

  /29

  $1,079,999

  $65K PRICE DROP

  • 7 Beds
  • 3 Baths

  2014 N Whipple St, Chicago, IL 60647

  Prime multi-unit investment opportunity offering both immediate cash flow and long-term stability. This well-maintained property is fully rented, including several long-term tenants, providing consistent income from day one. The two units have been recently renovated with modern finishes, while the upper levels remain occupied and performing. Located in the highly sought-after Logan Square

  Daniel Walus OnPath Realty Inc.

  2014 N Whipple St, Chicago, IL 60647
• 

  /2

  $515,000

  • 8 Beds
  • 3 Baths

  5139 W Washington Blvd, Chicago, IL 60644

  Turnkey investment opportunity! 3-unit building with extra-large apartments. 1st & 2nd floor units have hardwood floors. 2nd floor unit has washer & dryer hook-up. All units have separate utilities. Close to I-290 & Metra station. Units are currently rented MTM.

  Carmelo Rodriguez Extreme Realty LLC

  5139 W Washington Blvd, Chicago, IL 60644
• 

  /2

  $9,999

  • Land
  • 0 Sq Ft

  7358 S Marshfield Ave, Chicago, IL 60636

  Development Opportunity in West Englewood! 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 excellent opportunity to invest in an area with great potential for future appreciation.

  Chanee Roby Coldwell Banker Real Estate Group

  7358 S Marshfield Ave, Chicago, IL 60636
• 

  /2

  $245,000

  $20K PRICE DROP

  • 6 Beds
  • 2 Baths

  8037 S Sangamon St, Chicago, IL 60620

  This versatile two-story multi-family home features 6 bedrooms and 2 bathrooms, offering approximately 2,816 square feet of living space. With a 2-car garage and generous room sizes, this property is ideal for extended families or investment opportunities. Conveniently located with easy access to local amenities, shopping, and transportation this home combines space, function, and location. No

  Anthony Disano Parkvue Realty Corporation

  8037 S Sangamon St, Chicago, IL 60620
• 

  /2

  $105,000

  $20K PRICE DROP Pending

  • 6 Beds
  • 2 Baths

  7955 S Sangamon St, Chicago, IL 60620

  Excellent investment opportunity in the Auburn Gresham neighborhood of Chicago! This spacious 2-unit property offers strong potential for investors or rehabbers looking to add value. The building requires renovation, making it ideal for a full rehab project. Conveniently located near schools, parks, shopping, dining, and public transportation. Bring your vision and transform this property into a

  Claudia Jurado Realty of America, LLC

  7955 S Sangamon St, Chicago, IL 60620
• 

  

  /3

  $68,000

  • Land
  • 0 Sq Ft

  4603 S Wallace St, Chicago, IL 60609

  Great development opportunity on this well-located RS-3 zoned lot! Whether you are a developer, investor, or looking to build your dream home, this property offers excellent potential. The adjacent spacious single-family home at 4607 S Wallace St., featuring 4 bedrooms and 2.5 bathrooms, is also available and can be purchased together with the lot, providing an excellent opportunity for a

  Michael Ng Mango Realty Group

  4603 S Wallace St, Chicago, IL 60609
• 

  

  /18

  $345,000

  • 1 Bed
  • 1 Bath
  • 934 Sq Ft

  400 N Clinton St Unit 507, Chicago, IL 60654

  Experience the perfect blend of city energy and secluded tranquility in this meticulously maintained one-bedroom retreat within River North's coveted Kinzie Park gated community. Every inch of this home reflects a commitment to quality and detail, starting with the gleaming hardwood floors that flow seamlessly throughout the living/dining room and kitchen. At the heart of the home, the kitchen

  Kieran Conlon Compass

  400 N Clinton St Unit 507, Chicago, IL 60654
• 

  

  /19

  $475,000

  • 10 Beds
  • 4 Baths

  2518 S Claremont Ave, Chicago, IL 60608

  INVESTMENT OPPORTUNIYT! This huge brick two flat building located in the heart of Pilsen. Featuring two updated units, has plenty space and bedrooms in each unit, four full bathrooms and a full walk-up attic equipped with a bedroom and a bath for extra living space or duplex up with second floor unit. Two car garage! Located in a rapidly growing area for investment. Preferable cash or

  Ana Ramirez REMAX Legends

  2518 S Claremont Ave, Chicago, IL 60608
• 

  /2

  $459,000

  Pending

  • Studio
  • 1 Bath
  • 918 Sq Ft

  401 N Wabash Ave Unit 2141, 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 2141, Chicago, IL 60611
• 

  

  /42

  $747,000

  Pending

  • 8 Beds
  • 3 Baths

  7234 N Hamilton Ave, Chicago, IL 60645

  Turnkey Investment Property - Fully Rehabbed and Rented Legal 2 Flat with finished lower level. This beautifully rehabbed building is generating $6,500 in monthly income and ready for a hands-off investor. Each modern unit showcases a bright white kitchen with quartz countertops, stainless-steel appliances, and updated cabinetry, creating a clean, contemporary feel. Residents enjoy their own

  Amy Kite Keller Williams Infinity

  7234 N Hamilton Ave, Chicago, IL 60645
• 

  

  /18

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  2239 N Lister Ave Unit 201, Chicago, IL 60614

  Discover an outstanding investment opportunity in this beautifully maintained 3-bedroom, 2-bathroom condo ideally situated at the crossroads of Lincoln Park and Bucktown. This thoughtfully designed home features hardwood flooring throughout and an inviting open-concept layout that seamlessly connects the kitchen, dining, and living areas, creating a bright and functional living space. The kitchen

  Simeon Pawletki Chicago PM LLC

  2239 N Lister Ave Unit 201, Chicago, IL 60614
• 

  /2

  $10,000

  $5K PRICE DROP

  • Land
  • 0 Sq Ft

  6423 S Hermitage Ave, Chicago, IL 60636

  Exceptional opportunity for builders, developers, or savvy investors! This oversized 30x123 lot located at 6423 S Hermitage offers tremendous potential in a growing area surrounded by residential development and investment activity. Zoned RS-3, this parcel is ideal for a new construction single-family home or potential redevelopment opportunity (buyer to verify all zoning and building plans with

  Christopher Anthony Keller Williams ONEChicago

  6423 S Hermitage Ave, Chicago, IL 60636
• 

  

  /35

  $650,000

  $90K PRICE DROP

  • 6 Beds
  • 3 Baths

  1949 N Francisco Ave, Chicago, IL 60647

  Location, Location, Location !! Highly sought-after neighborhood California and Armitage. Walk to Blue line on Milwaukee Ave. Solid large tall handsome 3 apartment Brick building with an English garden unit with 2 entrances. Lots of woodwork. Hardwood floors. Good size apartments. Formal living Room and Dining Room. Plenty of closets. Spacious garden apartment . Enclosed Porch. Wide backyard.

  Ernesto Escalante Charles Rutenberg Realty

  1949 N Francisco Ave, Chicago, IL 60647
• 

  

  /17

  $242,500

  $13K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  4520 S King Dr Unit 1, Chicago, IL 60653

  This beautiful condo qualifies for the City of Chicago HomeGrown assistance program of up to $70,000! It must be your primary residence, but you don't have to be a first-time home buyer. Welcome home to this meticulously maintained 3-bedroom, 2-bath garden unit offering an impressive 1,500 square feet of comfortable living space in the heart of Bronzeville. Hardwood floors flow throughout the

  Tanya Cochran Coldwell Banker Realty

  4520 S King Dr Unit 1, Chicago, IL 60653
• 

  

  /23

  $250,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  910 N Lake Shore Dr Unit 1316, Chicago, IL 60611

  Bring your vision to this spacious 1 bedroom, 1 bath residence in one of Streeterville's iconic Mies van der Rohe-designed buildings. Featuring the architect's signature clean lines, floor-to-ceiling windows, and an expansive open layout, this home is ready for its next chapter. Offered as-is, this is an outstanding opportunity for investors, contractors, and buyers looking to customize a classic

  Tommy Choi Keller Williams ONEChicago

  910 N Lake Shore Dr Unit 1316, Chicago, IL 60611
• 

  

  /37

  $749,900

  Pending

  • 9 Beds
  • 6 Baths

  6835 S Clyde Ave, Chicago, IL 60649

  This is the one you've been waiting for! Welcome to 6835 S. Clyde Avenue, a stunning all-brick 3-flat in the heart of South Shore, just moments from Jackson Park, the lakefront, beaches, marinas, golf courses, Hyde Park, the University of Chicago, and the transformative Obama Presidential Center. Fully gutted and meticulously renovated from top to bottom, this exceptional property showcases

  Jessica Macey Real Broker LLC

  6835 S Clyde Ave, Chicago, IL 60649
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  /34

  $265,000

  • 4 Beds
  • 2 Baths

  331 W 76th St, Chicago, IL 60620

  Fully rehabbed and rented. Excellent investment property. Rent Roll attached and T-12 income statement. Please email listing agent if you are attending. Two CHA tenants and one market. Building is legal 2 unit with one non-conforming unit. Seller may apply to legalize unit under ADU ordinance. Only one unit will be shown on one scheduled day, next showing date to be scheduled week of 8.24 and

  Edward Reagan Safe Harbor Realty LLC

  331 W 76th St, Chicago, IL 60620
• 

  

  /13

  $230,000

  • Land
  • 2,613 Sq Ft
  • $3,833,333 per Acre

  2224 W Taylor St, Chicago, IL 60612

  Don't miss out on the opportunity to build in the thriving Tri-Taylor neighborhood! This unique corner lot parcel of land offers the perfect redevelopment potential for retail and or residential use, making it an ideal investment for investors or buyers looking to create their vision of the perfect home from the ground up. Why is This Lot So Exceptional: * Prime location: Situated on bustling

  Yvette DuPree @properties Christie's International Real Estate

  2224 W Taylor St, Chicago, IL 60612
• 

  

  /10

  $267,500

  $2K PRICE DROP

  • 5 Beds
  • 2 Baths

  124 W 108th Place, Chicago, IL 60628

  Rare opportunity to own a spacious 2-unit building with incredible income potential in a prime Chicago location ON A HUGE TRIPLE LOT! First time on the market in over a decade, this well-maintained property is perfect for investors or owner-occupants looking to build generational wealth. The first-floor unit offers 2 bedrooms and 1 bathroom, while the second-floor unit features 3 bedrooms and 1

  Eva Diaz ExaRealty LLC

  124 W 108th Place, Chicago, IL 60628
• 

  

  /23

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  8 E Randolph St Unit 1505, Chicago, IL 60601

  Welcome to refined city living in the heart of Chicago's Loop. Perfectly positioned among the city's iconic architecture, Millennium Park, the Chicago Riverwalk, world-class dining, premier shopping, acclaimed theaters, and vibrant nightlife, this exceptional residence offers an unparalleled lifestyle with everything just moments from your door. Bathed in natural light through expansive

  Vikki Kokuzian Compass

  8 E Randolph St Unit 1505, Chicago, IL 60601

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