Homes for Sale in Chicago, IL with 5-Bedrooms

• 

  

  

  /17

  $899,900

  • 9 Beds
  • 4 Baths

  2312 W Taylor St, Chicago, IL 60612

  Welcome to this beautifully maintained classic 2-unit brick building. Located in the vibrant Tri-Taylor neighborhood, just steps away from the Medical District and UIC campus. This prime location offers easy access to a variety of restaurants, shops, and public transportation options, making it perfect for investors and owner-occupants. All units have tenants on a month to month arrangement.

  ARACELY AVILA Coldwell Banker Realty

  2312 W Taylor St, Chicago, IL 60612
• 

  

  

  /20

  $295,000

  Pending

  • 6 Beds
  • 3 Baths

  6029 S Loomis Blvd, Chicago, IL 60636

  Great investment opportunity in the heart of Chicago! This well maintained 2-unit building offers spacious layouts, with each unit featuring 3 bedrooms, making it ideal for strong rental income potential. The finished basement adds additional usable space, perfect for extended living or storage. The property has undergone recent updates, providing added value and peace of mind for the next owner.

  Jaqueline Valenzuela Baird & Warner

  6029 S Loomis Blvd, Chicago, IL 60636
• 

  

  

  /12

  $385,000

  Pending

  • 8 Beds
  • 5 Baths

  6333 S Racine Ave, Chicago, IL 60636

  Discover this spacious and beautifully updated 2-flat offering comfort, functionality, and peace of mind. Unit 1 (Duplex-Down): 5 generously sized bedrooms, 3 full bathrooms, Modern kitchen with updated finishes, Lower-level family/recreational room ideal for entertaining. Unit 2: 3 bedrooms, 2 bathrooms. Bright and open floor plan, Updated kitchen and baths. 2025 Upgrades: Newly installed

  Wale Bello The Bello Portfolio LLC

  6333 S Racine Ave, Chicago, IL 60636
• 

  

  

  /34

  $875,000

  • 7 Beds
  • 3 Baths

  3600 S Union Ave, Chicago, IL 60609

  Welcome to 3600 S. Union Avenue, Chicago, IL. 60609 a meticulously maintained, 3 unit all brick building with 35 solar roof panels providing energy efficiency and cost savings, plus full walk-out basement!! Adjacent 4 car brick garage boasts (2) EV charging stations! Units feature spacious living/dining room combinations, new carpeting, with 2 bedrooms on the 1st and 2nd floors, and 3 bedrooms on

  Gale Ruggiero McColly Real Estate

  3600 S Union Ave, Chicago, IL 60609
• 

  

  

  /14

  $289,000

  Pending

  • 5 Beds
  • 3 Baths
  • 1,158 Sq Ft

  10557 S Indiana Ave, Chicago, IL 60628

  Gorgeous Cape Cod- Just Move Right In! Get ready to fall in love with this beautifully updated Cape Cod that perfectly blends timeless charm with modern, sleek finishes and generously sized rooms. Enter through the jaw dropping, open living and dining area, ideal for both everyday living and entertaining. The fresh, bright kitchen features crisp white cabinetry, newer stainless steel appliances,

  Sadeebra Watson Coldwell Banker Realty

  10557 S Indiana Ave, Chicago, IL 60628
• 

  

  /19

  $340,000

  $10K PRICE DROP Pending

  • 5 Beds
  • 2.5 Baths
  • 2,611 Sq Ft

  5632 S Christiana Ave, Chicago, IL 60629

  Located on a quiet residential street in the vibrant South Side of Chicago, this well-maintained home offers three levels of generous living space and classic Chicago charm. The home has been well taken care of by the owner and long term tenants. The property features a finished attic and basement that expand the home's versatility with two additional bedrooms, a kitchen, office space, storage,

  Annette Medina Realty of America, LLC

  5632 S Christiana Ave, Chicago, IL 60629
• 

  

  /23

  $599,900

  Pending

  • 6 Beds
  • 2 Baths

  2110 N Avers Ave, Chicago, IL 60647

  Well-maintained property with recent updates including fresh interior paint, new carpet, and a new roof on both the main house and garage, plus miscellaneous improvements throughout. The home provides a clean, functional layout and conveniently located near schools, parks, major roadways, and local amenities.

  Christopher Lobrillo Grandview Realty, LLC

  2110 N Avers Ave, Chicago, IL 60647
• 

  

  /29

  $419,000

  Pending

  • 5 Beds
  • 3 Baths
  • 912 Sq Ft

  5309 S Lawndale Ave, Chicago, IL 60632

  Welcome to this well-maintained brick Cape Cod located in the West Elsdon neighborhood. This property features 5 bedrooms and 3 full bathrooms, along with a spacious living room, dining room, and updated kitchen with newer cabinetry and stainless steel appliances. Recent improvements include thermal panel windows, updated bathrooms, refinished hardwood floors, and a newly installed roof. The full

  Liliana Gonzalez RE/MAX Mi Casa

  5309 S Lawndale Ave, Chicago, IL 60632
• 

  

  /29

  $1,599,900

  New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  3107 N Oakley Ave, Chicago, IL 60618

  Welcome to this stunning new-construction, 5-bedroom, 3.5-bath single-family home in the heart of West Lakeview. Nestled on a picturesque, tree-lined street, it showcases an inviting layout and stylish finishes throughout. Tall ceilings and gleaming hardwood floors fill the home with light and create a bright, open feel. Step past the charming front porch into the main level, where the living and

  Karen Schwartz Baird & Warner

  3107 N Oakley Ave, Chicago, IL 60618
• 

  

  /40

  $419,900

  Open Sat 12PM - 2PM

  • 6 Beds
  • 3 Baths
  • 4,868 Sq Ft

  8015 S Paxton Ave, Chicago, IL 60617

  8015 Paxton delivers the perfect mix of upscale living, comfort and city style elegance. This remodeled home is luxury living in South Shore as one of it's finest homes. Featuring 6 bedrooms and 3 Full Baths. Semi-Circle brick construction with nearly 5,000 square feet of finished living space. Step into a sun filled living room with hardwood flooring and black matte marble wood burning

  James Bohannon Enterprise Realty Power Broker

  8015 S Paxton Ave, Chicago, IL 60617
• 

  

  /13

  $149,900

  $50K PRICE DROP

  • 6 Beds
  • 3 Baths

  517 W Englewood Ave, Chicago, IL 60621

  Brick 3 unit; in need of total gut rehab.

  Nicholas Hansen Home One Realty

  517 W Englewood Ave, Chicago, IL 60621
• 

  

  /29

  $1,449,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 2,787 Sq Ft

  2036 W Barry Ave, Chicago, IL 60618

  Multiple Offers, Highest and Best due 5/5/2026 at noon. Fantastic opportunity in this brick and limestone newer home in Roscoe Village @ Hamlin Park. Main level features living room with fireplace and access to the front porch ,custom kitchen with island and pantry and adjoining dining room. Second floor offers primary suite with two walk in closets and spa like bath plus two more bedrooms and

  Grazyna Przybysz Chicago Area Realty Inc

  2036 W Barry Ave, Chicago, IL 60618
• 

  

  /8

  $44,900

  • 6 Beds
  • 3 Baths
  • 1,350 Sq Ft

  7629 S Maryland Ave, Chicago, IL 60619

  Large Frame home on quiet block featuring 6 bedrooms and 3 full baths. Needs a full rehab. Perfect for your next project. Large back yard. Sold as is. No survey provided.

  David Williamson Choice Realty Group Inc.

  7629 S Maryland Ave, Chicago, IL 60619
• 

  

  /28

  $384,000

  • 5 Beds
  • 4 Baths
  • 1,500 Sq Ft

  844 N Laramie Ave, Chicago, IL 60651

  Beautifully UPDATED oversized home offering an incredible amount of living space across THREE LEVELS. This well-maintained property features 4 FULL BATHROOMS, HUGE bedrooms including a spacious primary suite with SKYLIGHTS that fill the home with natural light, and an OPEN-CONCEPT layout perfect for entertaining and everyday living. The FULL FINISHED BASEMENT adds even more functional living

  Xochil Wendy Escobar Realty of America, LLC

  844 N Laramie Ave, Chicago, IL 60651
• 

  

  /57

  $349,900

  $70K PRICE DROP

  • 5 Beds
  • 4 Baths

  5758 S Honore St, Chicago, IL 60636

  Own and Earn!!! 4 flat Brick Building on Corner Lot!!! Well maintained by long term owners. Architected with front entrance and side entrance 2 units on front and 2 units on side. Total of 5 Bedrooms and 4 Baths. Full basement canvas for additional idea. Separate utilities. All units rented immediate income. Seller motivated. SCHEDULE YOUR PRIVATE SHOWING TODAY!!! Will show one unit initially and

  Pastor-Eric White Pearson Realty Group

  5758 S Honore St, Chicago, IL 60636
• 

  

  /59

  $1,995,000

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

  1443 N Cleaver St, Chicago, IL 60642

  Welcome to this exceptional luxury single-family home, offering approximately 4,500 square feet of thoughtfully designed living space with 6 bedrooms and 4.1 baths, located in a residential cul-de-sac. This stunning residence features an open-concept floor plan anchored by a dramatic floor-to-ceiling marble gas fireplace, creating a striking focal point for both everyday living and entertaining.

  Teresa Ramirez Chicago Premier Realty, Inc.

  1443 N Cleaver St, Chicago, IL 60642
• 

  

  /39

  $955,000

  $145K PRICE DROP

  • 6 Beds
  • 3 Baths

  2329 N Sacramento Ave, Chicago, IL 60647

  This prime Logan Square investment opportunity at 2329 N Sacramento Ave features three fully rented units and with recent capital improvements designed for long-term durability. The property is anchored by a 12-year-old built-up rubber bituminized roof that receives annual inspections and was refreshed with a silver coating four years ago. All windows were replaced within the last 20 years with

  Samantha Swaney GC Realty and Development

  2329 N Sacramento Ave, Chicago, IL 60647
• 

  

  /24

  $490,000

  • 5 Beds
  • 2 Baths

  2147 N Kilpatrick Ave, Chicago, IL 60639

  Outstanding 2-FLAT in western Hermosa owned by the same family for over 25 years! This well maintained 5-bed multi-unit includes a finished attic space and serves as the perfect investment property for every type of buyer. ZONED RS-3, both units offer plenty of living space and include newer appliances, true hardwood flooring, updated windows, and central heat! Whether needing an additional

  Ross Wall @properties Christie's International Real Estate

  2147 N Kilpatrick Ave, Chicago, IL 60639
• 

  

  /24

  $899,000

  Pending

  • 5 Beds
  • 3 Baths

  2920 N Lakewood Ave, Chicago, IL 60657

  Rare Lakeview 2-unit building offering a prime owner-occupant opportunity with built-in income potential.**This move-in ready building features a spacious 3-bedroom, 2-bath DUPLEX that lives like a single-family home, PLUS a 2-bedroom, 1-bath top-floor unit that can generate $2,500-$4,000/month in rental income. Current owner Airbnb's out the lower level of the duplex which grossed over $17K in

  Alifia Zotoff Baird & Warner

  2920 N Lakewood Ave, Chicago, IL 60657
• 

  

  /26

  $415,000

  • 6 Beds
  • 3 Baths

  3828 S Honore St, Chicago, IL 60609

  Great investment opportunity in the growing neighbood of McKinley Park! This multi-unit property features 3 Legal units with a total of 6 bedrooms and 3 baths, plus a finished attic, and 2 car garage. Live in one unit and rent the others for additional income. Conveniently located just minutes from Bridgeport, Pilsen, Chinatown. Easy access to trains, buses, highways, schools, partks, shopping,

  Guadalpe Rosales Duarte Realty Company

  3828 S Honore St, Chicago, IL 60609
• 

  

  /9

  $949,999

  Pending

  • 6 Beds
  • 3 Baths

  1728 N Francisco Ave, Chicago, IL 60647

  Unique multi units occupy by family for many years nicely maintain an oversized lot with newer garage and extra parking spaces for 2 or more cars, 606 trail right in your back yard by Western and California, located between Wicker Park and Humboldt Park. First floor unit has Central heat. All units are well maintain lots of improvements you wont be disappointed.

  Yolanda Arroyo Chicagoland Brokers, Inc.

  1728 N Francisco Ave, Chicago, IL 60647
• 

  

  /77

  $3,995,000

  • 7 Beds
  • 4.5 Baths
  • 5,676 Sq Ft

  2705 N Bosworth Ave, Chicago, IL 60614

  A once-in-a-generation opportunity awaits at 2705 Bosworth, a residence situated on an unimaginably rare, extra-wide 55' x 125' lot on one of the most serene, tree-lined corridors in the West Lincoln Park/DePaul neighborhood. This exceptional brick and limestone estate encompasses almost 5700 square feet of meticulously curated living space, offering a seamless blend of architectural grandeur,

  Jeanine McShea @properties Christie's International Real Estate

  2705 N Bosworth Ave, Chicago, IL 60614
• 

  

  /27

  $800,000

  $50K PRICE DROP

  • 12 Beds
  • 6 Baths

  4900 W Hubbard St, Chicago, IL 60644

  An investor's dream, welcome to 4900 W Hubbard Street, featuring four (4) above-grade two (2) bedroom one (1) bathroom units with two (2) in-law garden units, with impressively high ceilings. Each unit has in-unit washer and dryer, in addition to access to all unit mechanicals. Each unit has been renovated to bring it into 2026, but while still preserving common areas that retain the building's

  Joseph Reyna Real People Realty

  4900 W Hubbard St, Chicago, IL 60644
• 

  

  /26

  $400,000

  $40K PRICE DROP

  • 6 Beds
  • 2 Baths

  7227 S Michigan Ave, Chicago, IL 60619

  Turnkey Investment Opportunity - Fully Updated 2-Unit Building in Chatham/Park Manor Welcome to 7227 Michigan Ave-an exceptional opportunity to own a newly updated, income-producing building in the sought-after Chatham/Park Manor neighborhood. This well-maintained property features three spacious 3-bedroom, 1-bathroom apartments, making it ideal for investors seeking strong rental income or

  Colleen Berg Berg Properties

  7227 S Michigan Ave, Chicago, IL 60619
• 

  

  /35

  $680,000

  Pending

  • 8 Beds
  • 3 Baths

  4916 W Hutchinson St, Chicago, IL 60641

  **Multiple offers received. Highest and best due by Saturday, May 16, at 5 pm.** This beautifully maintained all-brick legal 2-flat with an in-law garden unit in sought-after Portage Park is an incredible investment opportunity or ideal owner-occupied property. Live in one unit while generating rental income from the others. Each oversized unit offers hardwood floors, three spacious bedrooms, a

  Megan Osberger Kale Realty

  4916 W Hutchinson St, Chicago, IL 60641
• 

  

  /40

  $1,649,000

  Pending

  • 6 Beds
  • 3.5 Baths

  5611 S Kenwood Ave, Chicago, IL 60637

  Nestled on a tree-lined cul-de-sac directly opposite Ray Elementary School playground, this prestigious rowhome was designed in 1903 by New York architectural firm Mann, MacNeille & Lindeberg in the classic Renaissance Revival style for University of Chicago academics and represents a rare opportunity on Hyde Park's storied Professor's Row. Beyond the stunning and well-preserved Gothic arched

  Chandra Shealey North Clybourn Group, Inc.

  5611 S Kenwood Ave, Chicago, IL 60637
• 

  

  /13

  $289,900

  • 5 Beds
  • 2 Baths

  7448 S Maplewood Ave, Chicago, IL 60629

  Huge investment opportunity! Solid brick 2-flat built in 1970 featuring a full basement, separate utilities, corner lot, and 2-car garage. Conveniently located near schools, parks, shopping, Metra station, and CTA bus stop. Great potential for investors or rehabbers. Don't miss this opportunity! Property is being sold AS IS. CASH ONLY.

  Slawomir Nowak Virtual Key Realty INC

  7448 S Maplewood Ave, Chicago, IL 60629
• 

  /2

  $999,880

  • 9 Beds
  • 6 Baths

  Unlisted Address

  *** AS-IS Sale *** Both Unit 1 & 2 occupied by tenants. DO NOT DISTURB tenant. Buyer's agent must accompany clients during showing. Unit 1 & 2 are same identical floor plan. Updated Kitchen with stainless steel appliances, maple cabinets, granite countertop. 2 unit building with all newer updates, Located within a 10 minute walk of the United Center. 1st FL covered extra 3br and 2 full baths apt

  Yvonne Yen Concentric Realty, Inc

  Unlisted Address
• 

  /2

  $6,950,000

  New Construction

  • 6 Beds
  • 7 Baths
  • 6,000 Sq Ft

  1865 N Burling St, Chicago, IL 60614

  Truly the last new construction opportunity on the most coveted block in Lincoln Park! The Savane Properties Design Build team presents an exceptional custom new construction home on the most desirable street in Chicago on a rare extra wide lot. This home offers 5 to 8 Bedrooms, 5 plus baths, state-of-the-art luxury finishes, expansive indoor/outdoor living spaces, lavish master suite, Front

  Tom Moran @properties Christie's International Real Estate

  1865 N Burling St, Chicago, IL 60614
• 

  /2

  $117,000

  Pending

  • 8 Beds
  • 3 Baths

  549 E 91st St, Chicago, IL 60619

  Property is available for online auction only. To see more details, additional photos, or to make an offer, please visit the Next Door Auctions website.

  Brian Brockman Bang Realty

  549 E 91st St, Chicago, IL 60619
• 

  

  /28

  $249,999

  Pending

  • 7 Beds
  • 4 Baths

  237 W 114th St, Chicago, IL 60628

  Spacious 2-Unit Duplex - Great Investment or Owner-Occupant Opportunity Well-maintained 2-unit duplex property featuring: 1st Floor: 4 bed / 1 bath currently vacant & used for storage .w/ den 2nd Floor: 3 bed / 1 bath currently vacant and move-in ready w/ den unfinished attic unfinished debasement w : washer & dryer hookups , new boiler fenced backyard , private driveway & parking Homeowners &

  Misael Chacon Beycome Brokerage Realty LLC

  237 W 114th St, Chicago, IL 60628
• 

  

  /3

  $201,450

  • 6 Beds
  • 3 Baths

  4837 S Union Ave, Chicago, IL 60609

  This 2 unit property offers 6 bedrooms and 2 bathrooms with approximately 2250 square feet of living space on a .06 acre lot. Each unit offers 3 bedrooms and 1 bathroom. No Buyer Premium on this property. The buyer has the right to select their own title/closing company. The buyer is responsible for all closing costs in this transaction. This asset is currently impacted by state redemption,

  Anthony Disano Parkvue Realty Corporation

  4837 S Union Ave, Chicago, IL 60609
• 

  

  /39

  $1,799,000

  • 6 Beds
  • 5.5 Baths
  • 5,300 Sq Ft

  3830 N Lowell Ave, Chicago, IL 60641

  Welcome to this beautiful home, located in the heart of historic Old Irving Park. Lovely extra large 40 x 144 lot with no alley behind affords coveted quiet and privacy so rarely found in the city. As you approach the brick entry and side drive, you will know you have arrived somewhere quite special. 2015 construction features classic and timeless finishes throughout all 4 living levels. An old

  Cara Buffa Berkshire Hathaway HomeServices Chicago

  3830 N Lowell Ave, Chicago, IL 60641
• 

  

  /33

  $795,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,678 Sq Ft

  2456 W Farwell Ave, Chicago, IL 60645

  Wonderful classic home with modern features and an open, flowing layout that seamlessly connects the kitchen, dining and living areas. Abundant natural light fills the space through large windows on the main level, creating a warm and inviting atmosphere.Perfectly positioned on an oversized 42x124 lot, this stunning home offers both space and comfort, inside and out. Lovingly maintained and

  MONICA ZAHA Optimus Realty Inc

  2456 W Farwell Ave, Chicago, IL 60645
• 

  

  /5

  $369,999

  Pre-Foreclosure

  • 6 Beds
  • 3 Baths

  4542 N Karlov Ave, Chicago, IL 60630

  Value on the land, also listed as a land! Over size Chicago lot 40 x 125, PERFECT FOR YOUR NEW HOUSE OR FOR A DEVELOPMENT, according to cook county assessor's website zoning allows up to 6 units on the lot, cute small park around the block. CASH ONLY OR LINE OF CREDIT, NO CONVENTIONAL LOAN WILL BE ACCEPTED, Property is being sold "As is conditions". currently Legal Two unit with extra living

  Adriana Rivera Realty of America, LLC

  4542 N Karlov Ave, Chicago, IL 60630
• 

  

  /21

  $314,999

  $45K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 2,000 Sq Ft

  7545 S Rhodes Ave, Chicago, IL 60619

  Greater Grand Crossing - Fully Rehabbed Brick Bungalow with Modern Luxury and Space to Spare! Welcome to this beautifully renovated 6-bedroom, 2-bath brick bungalow where timeless Chicago charm meets high-end finishes. This stunning home has been thoughtfully updated from top to bottom, showcasing elegant marble details throughout and a seamless blend of classic character with contemporary style.

  Michael Woloszczuk Avenue Properties Chicago

  7545 S Rhodes Ave, Chicago, IL 60619
• 

  

  /8

  $299,000

  Pending

  • 8 Beds
  • 2 Baths

  7332 S Luella Ave, Chicago, IL 60649

  Investor special in the heart of South Shore! This classic 2-flat at 7332 S Luella Ave blends timeless architecture with strong income potential, perfect for an owner-occupant or savvy investor. Each unit features 4 bedrooms, 1 bathroom, and an enclosed back porch, offering generous living space and flexibility. Inside, you'll appreciate the original stained glass, rich woodwork, and

  Shawanna Bryant Keller Williams Innovate

  7332 S Luella Ave, Chicago, IL 60649
• 

  

  /42

  $299,000

  Pending

  • 5 Beds
  • 2 Baths
  • 1,100 Sq Ft

  11613 S Loomis St, Chicago, IL 60643

  Stunning fully rehabbed Chicago home offering 5 bedrooms, 2 updated bathrooms, and modern finishes throughout! Step inside to an open and bright layout featuring new flooring, recessed lighting, and a stylish electric fireplace accent wall. The beautifully updated kitchen boasts white shaker cabinets, quartz countertops, stainless steel appliances, and designer finishes. The finished basement

  Frank Montro Keller Williams Preferred Rlty

  11613 S Loomis St, Chicago, IL 60643
• 

  

  /46

  $439,800

  Pending

  • 6 Beds
  • 3 Baths
  • 2,161 Sq Ft

  2936 N Kenneth Ave, Chicago, IL 60641

  Beautiful brick bungalow located on a highly desirable block! This well-maintained home is filled with natural light and features beautiful hardwood floors, a spacious living room, separate dining area, generously sized bedrooms, and a large kitchen perfect for everyday living and entertaining. The finished basement offers excellent ceiling height, providing additional living space with endless

  Gonzalo Santoyo HomeSmart Connect LLC

  2936 N Kenneth Ave, Chicago, IL 60641
• 

  

  /27

  $310,000

  Pending

  • 5 Beds
  • 2 Baths
  • 1,650 Sq Ft

  6337 S Rockwell St, Chicago, IL 60629

  Charming 5 bedroom (with a potential 6th), 2 bath classic Bungalow ready for new owners! As you arrive at the home you're greeted by a gated front yard and a large covered porch. Inside, the living room and separate dining room have plenty of natural light and beautiful hardwoods that flow throughout the main level. The updated kitchen features granite countertops, stainless steel appliances and

  Cesar Juarez Redfin Corporation

  6337 S Rockwell St, Chicago, IL 60629

Showing Results 401 - 440, Page 11 of 18