5-Bedroom Homes for Sale in Chicago, IL

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  /3

  $168,000

  • 8 Beds
  • 3 Baths

  7043 S Yale Ave, Chicago, IL 60621

  Brick 2-Unit with 8 Bedrooms & Expandable Basement Space! If you're ready to boost your portfolio, you don't want to sleep on this cash-flow opportunity! This well-positioned two-flat in the popular Englewood community, offers generous space and excellent rental upside! With 4 spacious bedrooms in each unit, you'll have a total of 8 bedrooms-ideal for maximizing rental income. The partially

  

  Tamika Marks

  Trademarks & Associates

  (312) 313-8205

  7043 S Yale Ave, Chicago, IL 60621
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  /33

  $1,699,900

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

  1150 E 49th St, Chicago, IL 60615

  Custom renovation in Historic Kenwood! Sophisticated single-family home offers a perfect blend of mid-century charm and modern living. Large garden is a lovely oasis which includes a private pergola and formal dining area. Dine al fresco with family and friends using the large outdoor cooking area and expansive front yard. The home was completely reconstructed to the studs by the owner. The

  

  Kimberly Chase-Harding

  Berkshire Hathaway HomeServices Chicago

  (773) 945-0384

  1150 E 49th St, Chicago, IL 60615
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  /25

  $80,000

  • 5 Beds
  • 2 Baths
  • 1,536 Sq Ft

  7207 S Winchester Ave, Chicago, IL 60636

  Price Just Improved!!! Now priced to move - bring your vision and build equity in West Englewood! Don't miss your second chance to unlock the potential of this spacious 5-bedroom, 2-bath home tucked away on a quiet block in one of Chicago's revitalizing neighborhoods. Featuring a full basement ready for your creative ideas, a 2-car garage, and a huge rear yard-this property offers the space and

  

  Tamika Marks

  Trademarks & Associates

  (312) 584-2746

  7207 S Winchester Ave, Chicago, IL 60636
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  /32

  $585,000

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

  2950 N Lowell Ave, Chicago, IL 60641

  Welcome to this beautiful, renovated house. Discover the potential that it has to offer, be ready for ideas of the options you will have with three levels of living and outstanding 8 bedrooms throughout the house. First level offers 3 bedrooms one bath, nicely polished hardwood floors throughout and a beautiful kitchen in white accents. Second floor features extended living with two bedrooms and

  

  Osbaldo Perez

  Chicagoland Brokers, Inc.

  (312) 847-3158

  2950 N Lowell Ave, Chicago, IL 60641
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  /31

  $519,900

  • 5 Beds
  • 3 Baths
  • 2,756 Sq Ft

  6321 N Merrimac Ave, Chicago, IL 60646

  Wow! 5 Bedroom, 3 full bath, English Tudor on a tranquil, tree lined street in Norwood Park. First floor features a beautifully updated eat in kitchen with new appliances, separate formal dining room, two large bedrooms, new designer full bath & oversized family room with gas fireplace overlooking lush green yard. Second floor includes three bedrooms and rehabbed full bath. Finished basement

  

  John Vodopic

  Coldwell Banker Realty

  (312) 874-6136

  6321 N Merrimac Ave, Chicago, IL 60646
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  /22

  $389,999

  • 5 Beds
  • 2 Baths

  5726 S Elizabeth St, Chicago, IL 60636

  Discover this completely rehabbed 2-unit brick building in West Englewood. Gutted down to the studs, this property boasts brand new everything-roof, electrical, plumbing, and more! Rest peacefully knowing all city permits were pulled. Unit 1 (Duplex-Down): A spacious 2-bedroom, 1-bath layout with hardwood flooring, elegant wainscoting, and a modern kitchen featuring stainless steel appliances.

  

  Tina Hollins

  Coldwell Banker Realty

  (312) 313-4613

  5726 S Elizabeth St, Chicago, IL 60636
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  /20

  $415,000 Open Sat 11AM - 12PM

  • 6 Beds
  • 3 Baths

  1547 S Kolin Ave, Chicago, IL 60623

  Elevate your investment portfolio with this impressive income generating three unit property in the heart of North Lawndale. Each unit boasts a comfortable layout, featuring two bedrooms and a full bathroom, complemented by modern stainless steel appliances for a touch of sophistication. Notably, two of the units underwent a comprehensive rehabilitation in 2024, showcasing updated kitchens and

  

  Danisha Jones

  Coldwell Banker Realty

  (773) 250-3638

  1547 S Kolin Ave, Chicago, IL 60623
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  /24

  $1,895,000

  • 6 Beds
  • 6 Baths
  • 5,127 Sq Ft

  4942 S Ellis Ave, Chicago, IL 60615

  Huge Sunny Hyde Park/South Kenwood 6 bedroom Greystone is totally upgraded and has space to add a 2 car garage. Note that this Greystone is an end unit and is therefore only attached on one side and thus gets lots of light. This move-in ready elegant home has an open floor plan which is designed for entertaining. This home has maintained all the vintage details: built in book cases,

  

  Shirley Walker

  Berkshire Hathaway HomeServices Chicago

  (872) 312-2609

  4942 S Ellis Ave, Chicago, IL 60615
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  /40

  $274,999 Open Sat 12PM - 2PM

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

  10617 S Wentworth Ave, Chicago, IL 60628

  Welcome to 10617 S Wentworth Ave Step into this beautifully newly renovated gem, offering 5 spacious bedrooms and 3 modern bathrooms. Perfect for growing families or anyone who loves to entertain. Every inch of this home has been thoughtfully upgraded, blending contemporary style with timeless charm. The stunning kitchen is a true showstopper, featuring sleek countertops, brand-new cabinetry, and

  

  Rafay Qamar

  Real Broker LLC

  (312) 854-8691

  10617 S Wentworth Ave, Chicago, IL 60628
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  /29

  $509,000

  • 5 Beds
  • 3 Baths

  5443 S Nottingham Ave, Chicago, IL 60638

  DESIREABLE GARFIELD RIDGE. LEGAL 2 UNIT. 3 BEDROOM 1ST FLOOR. 2 BEDROOMS ON 2ND FLOOR. TOTAL 3 BATHROOMS WITH BATHROOM IN BASEMENT. BASEMNT IS FINISHED AND HAS KITCHEN. GREAT FOR FAMILY ENTERTAINMENT OR STORAGE. NEWER GARAGE WITH PARTY DOOR TO FENCED BACKYARD. CLOSE TO SCHOOLS, SHOPPING., TRANSPORTATION, & AIRPORT.HOUSE IS BEING SOLD AS IS BUT HAS GREAT BONES. CALL AND MAKE YOUR APPOINTMENT.

  

  John Wanda

  Century 21 Circle

  (312) 477-2224

  5443 S Nottingham Ave, Chicago, IL 60638
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  /45

  $855,000

  • 6 Beds
  • 4 Baths

  3322 N Kostner Ave, Chicago, IL 60641

  Opportunity awaits with this rare 2-flat plus newly converted coach house, situated on two full lots in the highly desirable Irving Park community of Chicago. The main two-story building features a spacious first-floor unit with 2 bedrooms and 1 bath, ideal for families or rental income. The second-floor unit is duplexed and offers 3 bedrooms and 1.5 baths with a comfortable and functional

  

  Rafay Qamar

  Real Broker LLC

  (312) 313-8736

  3322 N Kostner Ave, Chicago, IL 60641
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  /48

  $1,625,000

  • 6 Beds
  • 2 Baths

  2732 W Belmont Ave, Chicago, IL 60618

  Incredibly Rare opportunity to own this multifaceted one-of-a-kind property with unmatched potential and versatility offering a fully Stabilized All Brick 2-Unit building updated to modern standards and fully renovated with contemporary condo quality finishes + a Huge 1,800 sqft All Brick original carriage house/garage w/16.5' ceiling height offering extensive/creative use potential + an

  

  Cyrus Seraj

  Compass

  (312) 313-3508

  2732 W Belmont Ave, Chicago, IL 60618
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  /29

  $289,000

  • 6 Beds
  • 2 Baths

  817 W 54th St, Chicago, IL 60609

  Solid Brick Two-Unit Income Property in New City! This well-maintained building features two spacious 3-bedroom units, each offering a bright living room, formal dining room, and full bath. Updated mechanicals and separate heating systems mean tenants pay all utilities-a smart setup for investors or owner-occupants seeking added income. The full open basement currently serves as the laundry and

  

  Tamika Marks

  Trademarks & Associates

  (872) 328-4127

  817 W 54th St, Chicago, IL 60609
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  /14

  $114,900

  • 5 Beds
  • 2 Baths

  6812 S Hermitage Ave, Chicago, IL 60636

  The property here is a frame 2 flat with plenty of upswing potential. Bring your TLC ideas to this property and make it your own. Great rental potential and walking distance to school. Location, location, location this is the one set your appointment Today as this one is a must see. Bring all offers and the property is sold in "AS IS" condition. My seller has multiple offers and is

  

  Otis Lazich

  Capital Investment Realty Group Inc

  (872) 326-1473

  6812 S Hermitage Ave, Chicago, IL 60636
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  /39

  $379,000

  • 6 Beds
  • 3 Baths
  • 2,969 Sq Ft

  7545 S Perry Ave, Chicago, IL 60620

  Step into this beautifully reimagined 6-bedroom, 3-bathroom home in the heart of Greater Grand Crossing, offering three full levels of thoughtfully designed living space. With a seamless blend of modern style and comfort, this home is ideal for both everyday living and memorable entertaining. The main level welcomes you with a bright, open-concept layout featuring a sun-drenched living room

  

  Leticia Jimenez

  @properties Christie's International Real Estate

  (773) 912-0405

  7545 S Perry Ave, Chicago, IL 60620
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  /22

  $310,000

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

  11423 S Calumet Ave, Chicago, IL 60628

  Welcome to this beautifully renovated 5-bedroom, 2-bathroom brick home in Chicago's West Pullman neighborhood. This spacious home combines classic charm with modern upgrades, featuring new finishes and thoughtful touches throughout. Step inside to discover an open-concept living area flooded with natural light, highlighted by newly installed luxury vinyl flooring and fresh paint. The brand-new

  

  Arianne Kendrick

  Coldwell Banker Realty

  (872) 331-4096

  11423 S Calumet Ave, Chicago, IL 60628
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  /19

  $150,000

  • 7 Beds
  • 2 Baths
  • 2,800 Sq Ft

  7051 S Princeton Ave, Chicago, IL 60621

  Spacious single-family home featuring 7 rooms plus 2 additional rooms in the basement and 2 full bathrooms. All bedrooms are generously sized, offering flexible living space. The property needs some work but has great upside for the right buyer. Large backyard provides plenty of outdoor space. Perfect for investors or homeowners looking to customize and add value. Don't miss this opportunity!

  

  Randy Aucapina

  Smart Home Realty

  (872) 259-9384

  7051 S Princeton Ave, Chicago, IL 60621
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  /3

  $100,000

  • 9 Beds
  • 3 Baths

  5427 S Princeton Ave, Chicago, IL 60609

  Excellent investment opportunity in the heart of Back of the Yards! This 3 Unit Building is in need of a full rehab and offers a solid foundation for your next project. City-approved plans and permits are already in place, saving you time and hassle. Great potential to customize and add value. Buyers are encouraged to do their due diligence. Ideal for seasoned investors or rehabbers looking for a

  

  Randy Aucapina

  Smart Home Realty

  (872) 326-8738

  5427 S Princeton Ave, Chicago, IL 60609
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  /19

  $255,000

  • 6 Beds
  • 3 Baths

  12256 S Union Ave, Chicago, IL 60628

  Don't miss this fantastic two-unit property located in the heart of West Pullman, Chicago-an excellent find for both homeowners and savvy investors. The first-floor unit features a cozy 2-bedroom layout, perfect for individuals or small families. Upstairs, the second unit offers 4 spacious bedrooms, ideal for larger families or multiple tenants. Situated near public transportation and interstate,

  

  James Morris

  JMRI Corp

  (872) 253-7909

  12256 S Union Ave, Chicago, IL 60628
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  /147

  $499,000

  • 9 Beds
  • 6 Baths

  6331 S Throop St, Chicago, IL 60636

  Well-maintained 4-unit building with all units recently updated. Great opportunity to live in one unit and rent the others, or add to your investment portfolio. Exterior improvements include new windows and some tuckpointing. Each unit features updated kitchens with granite countertops, hardwood floors, new doors and trim, and modern bathrooms with ceramic tile. Freshly painted throughout. A

  

  David Hernandez

  Coldwell Banker Realty

  (773) 570-1041

  6331 S Throop St, Chicago, IL 60636
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  /34

  $349,500

  • 8 Beds
  • 3 Baths

  6927 S Hermitage Ave, Chicago, IL 60636

  This Recently Renovated (2020) 2 flat + Garden offers flexibility to the investor that adds this property to their portfolio. With one unit newly vacant and freshly painted - FHA or owner occupied Buyers are welcomed! The two occupied units are current and at or near Market Rates w/ MTM leases. This building has been well maintained to date, all three units feature Condo Quality Finishes, SS

  

  Brandy Bell

  Baird & Warner

  (312) 584-1447

  6927 S Hermitage Ave, Chicago, IL 60636
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  /35

  $390,000

  • 5 Beds
  • 3 Baths

  2814 W 25th Place, Chicago, IL 60623

  Perfect for the savvy Investor! Rehabbed Brick 2 flat! 1st floor offers 3 bedrooms, 1.5 baths, spacious living room and kitchen. Currently rented. The second floor unit offers 2 bedrooms, 1 bath, living room and dining room. The unfinished attic space is ideal for a duplex up for an additional bedroom, living space or storage. Currently rented. New flooring throughout. 2022 and 2023 new

  

  Rafay Qamar

  Real Broker LLC

  (872) 253-7954

  2814 W 25th Place, Chicago, IL 60623
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  /78

  $3,100,000

  • 7 Beds
  • 6.5 Baths
  • 7,000 Sq Ft

  5235 S University Ave, Chicago, IL 60615

  Stunning and impressive Hyde Park home and coach house designed by architect, James Gamble Rogers, is a short walking distance to The University of Chicago campus and hospital. This Collegiate Gothic architecture is similar to The University of Chicago impressive Gothic buildings. This home is filled with original classical architectural details and is tastefully updated to fit today's modern

  

  Shirley Walker

  Berkshire Hathaway HomeServices Chicago

  (872) 278-4641

  5235 S University Ave, Chicago, IL 60615
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  /2

  $319,000

  • 6 Beds
  • 2 Baths

  3637 S Hermitage Ave, Chicago, IL 60609

  FHA REHAB LOAN, CONVENTIONAL ,CASH

  

  Ernestina Preciado

  RE/MAX 10

  (872) 278-6238

  3637 S Hermitage Ave, Chicago, IL 60609
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  /2

  $85,000

  • 5 Beds
  • 2 Baths

  7122 S Seeley Ave, Chicago, IL 60636

  Investor Special! Spacious 5BR/2BA Home with Huge Potential Attention investors! This large dormered 5-bedroom, 2-bathroom home is a fantastic opportunity for a fix-and-flip or buy-and-hold investment. Located on a great block, this property offers incredible potential to maximize returns. Sold As-Is and sight unseen as it is currently occupied. Don't miss out on this high-potential

  

  Oscar Arteaga

  Keller Williams Infinity

  (872) 327-4188

  7122 S Seeley Ave, Chicago, IL 60636
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  /14

  $340,000

  • 7 Beds
  • 2 Baths

  2849 S Kolin Ave, Chicago, IL 60623

  2 flat located in the heart of Little Village. 5 minutes from Shopping area, park and restaurants. Roof, Furnace on 1st floor and 2nd floor all installed in 2019 A/C 2020 Water tank on 2nd floor 2024. The attic has one bedroom, and planty of storage

  

  George Medina

  Realty of America

  (773) 570-7360

  2849 S Kolin Ave, Chicago, IL 60623
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  /16

  $579,900

  • 6 Beds
  • 3 Baths

  2014 N Western Ave, Chicago, IL 60647

  Rare two-flat with in-law unit in prime Chicago location! Situated on B3-2 zoning, this property offers excellent redevelopment potential-whether as a retail storefront with residential units above or other mixed-use possibilities. Property is in need of TLC and is priced accordingly. Home has been professionally appraised and will be sold as-is. Excellent access to I-90/94, the Blue Line, and

  

  Karina Hiselman

  Compass

  (773) 300-4968

  2014 N Western Ave, Chicago, IL 60647
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  /21

  $127,900

  • 5 Beds
  • 1.5 Baths
  • 1,107 Sq Ft

  5020 S May St, Chicago, IL 60609

  Excellent investment opportunity! This spacious 5-bedroom, 1.5-bath home is ideal as a large family rental or an owner-occupied residence with room to grow. The main level offers four bedrooms and a full bath, while the mostly finished basement includes a generous family room, fifth bedroom, half bath, and ample storage. The oversized eat-in kitchen provides plenty of cabinet space and table

  

  James Morris

  JMRI Corp

  (312) 663-8628

  5020 S May St, Chicago, IL 60609
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  /63

  $999,999 Open Sat 12PM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  3406 N Keating Ave, Chicago, IL 60641

  United Chicago Builders Luxury Collection | 2019 RED Luxe Award Winner Stunning custom-built 5BD/3.1BA home by United Chicago Builders, combining timeless design with modern luxury on an oversized, non-standard lot. Ideally located steps from the park and just 15 15-minute Metra ride to Downtown Chicago, expressways, and grocery stores. Highlights include: Bright open layout with soaring

  

  Sohe Reyes

  Smart Home Realty

  (773) 974-6898

  3406 N Keating Ave, Chicago, IL 60641
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  /28

  $429,900

  • 7 Beds
  • 2 Baths

  6932 S Green St, Chicago, IL 60621

  Welcome to this beautifully updated multi-unit property in the heart of Englewood. Fully renovated in 2020, this home features gleaming hardwood floors throughout, updated kitchens, modern baths, and thoughtful finishes that blend comfort with style. Each unit offers spacious layouts filled with natural light, while the unfinished basement is a blank canvas with a roughed-in bathroom, perfect

  

  LaToya Moore

  Baird & Warner

  (312) 605-1908

  6932 S Green St, Chicago, IL 60621
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  /8

  $400,000

  • 6 Beds
  • 2 Baths

  6621 S Marquette Dr, Chicago, IL 60637

  Renovated Two-Unit Greystone in West Woodlawn! This classic Chicago Greystone features two spacious 3 bed, 1 bath units, each updated with hardwood floors, stainless steel appliances, countertops, and modern finishes. Renovated in 2024 before the current tenants moved in. Underground plumbing replaced and updated in 2023 from the building to street. The unfinished basement offers potential for a

  

  Devin Burks

  @properties Christie's International Real Estate

  (312) 815-2038

  6621 S Marquette Dr, Chicago, IL 60637
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  /46

  $350,000

  • 6 Beds
  • 3 Baths

  7305 S Harvard Ave, Chicago, IL 60621

  Don't miss out on this incredible money-maker! This spacious multi-family home is now available-and it won't last long. Nestled in a desirable neighborhood, this property features two generous 3-bedroom units, making it ideal for investors looking for strong rental income or for those seeking a flexible layout for multi-generational living. Sitting proudly on a rare double lot, this home provides

  

  Rafay Qamar

  Real Broker LLC

  (312) 663-8232

  7305 S Harvard Ave, Chicago, IL 60621
• 

  

  /22

  $425,000

  • 7 Beds
  • 2 Baths

  4251 W Jackson Blvd, Chicago, IL 60624

  Welcome to Jackson. This solid brick 2-unit building features two spacious units - perfect for investors or multigenerational living. The first-floor unit offers 3 bedrooms and 1 full bath, currently leased to a reliable tenant. The second-floor unit, previously owner-occupied, boasts 4 bedrooms and 1 full bath with generous living space and natural light. Both units feature separate utilities

  

  Sohe Reyes

  Smart Home Realty

  (312) 681-7489

  4251 W Jackson Blvd, Chicago, IL 60624
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  /31

  $769,000

  • 11 Beds
  • 5 Baths

  5943 S Indiana Ave, Chicago, IL 60637

  Timeless Greystone 3 flat building is now available for you in RED HOT Washington Park neighborhood of Chicago. As the owner, you have the flexibility of living in the top floor unit while collecting stable market rents from the tenants on first and second floor, or rent the top floor unit and max out your income!!! Hardwood floors THROUGHOUT each unit. First floor unit is a Duplex down and

  

  John Wright

  Keller Williams Premiere Properties

  (312) 997-5039

  5943 S Indiana Ave, Chicago, IL 60637
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  /17

  $750,000

  • 9 Beds
  • 6 Baths

  450 W 29th St, Chicago, IL 60616

  Solid brick legal 2-unit located in the heart of Bridgeport! This well-maintained masonry home features a finished basement and offers great flexibility for owner-occupants or investors. Each unit has its own spacious layout, and the property includes a washer and dryer on both the second floor and basement levels for added convenience. Perfect for multigenerational living or rental income, this

  

  Cinny Chui

  Century 21 Realty Associates

  (312) 579-0894

  450 W 29th St, Chicago, IL 60616
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  /38

  $429,900

  • 5 Beds
  • 3 Baths

  8030 S Trumbull Ave, Chicago, IL 60652

  Newly Listed! Rare Opportunity in Ashburn Rarely available and impeccably maintained, this solid brick 2-flat with a fully finished basement in-law suite presents an incredible opportunity for both savvy investors and owner-occupants. Located in the heart of a Mobility Area, this property is ideal for maximizing rental income and long-term value. Each unit features a spacious layout with

  

  Shanara Carter

  eXp Realty

  (312) 284-3231

  8030 S Trumbull Ave, Chicago, IL 60652
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  /9

  $450,000

  • 6 Beds
  • 4 Baths

  3960 S Western Ave, Chicago, IL 60609

  Wow! This property has been upgraded, rehabbed and reimagined creating 4 units of living space. First floor has 2 units( Front 2 bedroom & 1 bathroom) (Back unit is 1 bedroom & 1 bathroom), Second floor has a 2 bedroom & 1 bathroom, lower level is 1 bedroom and 1 bathroom. Units were all gut rehabbed, new kitchens, new bathrooms and hardwood floors. Tons of opportunity to live in a unit

  

  Mary Aloisio

  @properties Christie's International Real Estate

  (312) 462-1703

  3960 S Western Ave, Chicago, IL 60609
• 

  

  /43

  $285,000

  • 5 Beds
  • 2 Baths

  7240 S Langley Ave, Chicago, IL 60619

  This exceptional investor property features two units, making it a perfect opportunity for those looking to expand their portfolio. Located in growing neighborhood, the property offers consistent rental income potential with its spacious layout and prime location. Each unit boasts generous living spaces, updated kitchens, and ample natural light, offering tenants a comfortable and attractive

  

  Rafay Qamar

  Real Broker LLC

  (312) 313-0970

  7240 S Langley Ave, Chicago, IL 60619
• 

  

  /13

  $249,900

  • 6 Beds
  • 2 Baths

  7948 S Union Ave, Chicago, IL 60620

  Discover a fantastic investment opportunity in the heart of the vibrant Auburn Gresham neighborhood, this property offers easy access to local amenities, schools, parks, and public transportation! Whether you're an investor looking for rental income or a homeowner interested in house hacking and living in one unit while renting out the other, this property provides a fantastic opportunity. The

  

  Reginald Patterson

  eXp Realty

  (312) 313-3018

  7948 S Union Ave, Chicago, IL 60620
• 

  

  /16

  $499,000

  • 5 Beds
  • 3 Baths
  • 2,024 Sq Ft

  3124 N 76th Ave, Elmwood Park, IL 60707

  WOW 5 BEDROOMS & 3 FULL BATHROOMS. BEST VALUE IN ELMWOOD PARK. Just remodeled with new hard wood floors, updated beautiful kitchen and all new bathrooms. If you're looking for a massive amount of space in a great neighborhood, close to everything, then this is it! The living room features a large picture window and there are hardwood floors throughout the whole first floor. The large dining

  

  Mary Aloisio

  @properties Christie's International Real Estate

  (708) 249-3845

  3124 N 76th Ave, Elmwood Park, IL 60707

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