5-Bedroom Homes for Sale in Chicago, IL

• 

  

  

  /25

  $249,900

  • 5 Beds
  • 2 Baths
  • 3,554 Sq Ft

  10001 S Wentworth Ave, Chicago, IL 60628

  Welcome to this spacious and recently renovated 5 bedroom 2 bathroom single-family home. Step inside to discover beautiful hardwood floors and spacious floorplan, perfect for accommodating a growing family or hosting gatherings. The kitchen boasts white shaker cabinets, quartz countertops , stainless steel appliances and an open-concept design. The full basement provides additional storage

  Mary Derman Keller Williams Preferred Rlty

  10001 S Wentworth Ave, Chicago, IL 60628
• 

  

  

  /32

  $455,000

  • 7 Beds
  • 3 Baths

  4336 W Adams St, Chicago, IL 60624

  Gorgeous Greystone in Hot West Garfield! This unique 2 flat has just been rehabbed and boasts 7 bedrooms and 3 baths! The first floor has been duplexed to the basement with 2 bedrooms and a bath on each floor. Perfect for an owner's unit. Perfect investment for owner occupied, cash flow play, or related living! ! Too many upgrades to mention. Come check it out before it's gone!

  Ryan Cherney Circle One Realty

  4336 W Adams St, Chicago, IL 60624
• 

  

  

  /22

  $175,000

  • 5 Beds
  • 2 Baths
  • 1,470 Sq Ft

  256 W 112th Place, Chicago, IL 60628

  Discover this freshly renovated (2025) 5-bedroom, 2-bathroom single-family home on a spacious corner lot in Chicago's South Side. This property is perfect for families looking for more space or investors seeking a strong rental opportunity. Inside, you'll find new carpet, luxury vinyl flooring, and fresh paint throughout. The modern kitchen features newer appliances, quartz countertops, and

  Luis Ortiz Shield Real Estate

  256 W 112th Place, Chicago, IL 60628
• 

  

  

  /12

  $600,000 Open Sat 12PM - 2PM

  • 9 Beds
  • 6 Baths

  6807 S Paulina St, Chicago, IL 60636

  This newly renovated 3-unit brick building is the perfect opportunity for both investors and owner-occupants. Each spacious unit offers 3 bedrooms and 2 full bathrooms, along with beautifully updated kitchens featuring butcher block countertops, farmhouse sinks, and stainless steel appliances. Washer and dryer hookups add convenience to each home. The property also features a low-maintenance

  Lonzetta McKennie @properties Christie's International Real Estate

  6807 S Paulina St, Chicago, IL 60636
• 

  

  

  /31

  $529,000

  • 9 Beds
  • 3 Baths

  4938 W Rice St, Chicago, IL 60651

  Perfectly located on quiet tree lined street in the heart of Austin and meticulously updated throughout on a oversized 30' x 125' lot with new electricals, plumbing, and HVAC. Completely renovated 2 legal units with fully finished garden unit with separate utilities. The living room boast oversized windows with abundance of natural light. Highly upgraded kitchen with microwave, dishwasher,

  Brian Waters Mentor Listing Realty Inc.

  4938 W Rice St, Chicago, IL 60651
• 

  

  /26

  $750,000

  • 7 Beds
  • 3 Baths

  5814 N Campbell Ave, Chicago, IL 60659

  This updated and well maintained 2-Flat with garden apartment is situated on an extra-wide lot along a picturesque, tree-lined street in the desirable Arcadia Terrace Neighborhood. The building's wider footprint allows for spacious room sizes throughout. The first-floor kitchen is brand new, featuring high-end finishes and an open layout that connects seamlessly to the dining room, creating a

  Michael Hall Baird & Warner

  5814 N Campbell Ave, Chicago, IL 60659
• 

  

  /35

  $549,000

  • 5 Beds
  • 3 Baths

  5532 S Kilbourn Ave, Chicago, IL 60629

  Completely remodeled and updated property with stainless steel appliances, new cabinets and countertops, new Brazilian Cherry hardwood floors all around, new glass handrails, new bathrooms, etc. Everything is new including the entire electrical system, new copper water lines everywhere, new gas lines, etc. Must see property that can easily be rented or used for AirBNB because it is within

  Ryan Cherney Circle One Realty

  5532 S Kilbourn Ave, Chicago, IL 60629
• 

  

  /26

  $924,500

  • 5 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  3123 W Chase Ave, Chicago, IL 60645

  Beautifully maintained West Rogers Park home with spacious brick addition offering 5 bedrooms and 4.5 baths. The second floor features 5 bedrooms, including a primary suite with walk-in closet and full bath, plus ample closet space throughout. Main level highlights include hardwood floors, formal dining room, powder room, large family room, and a bright kitchen with generous cabinet and counter

  Joseph Hartman eXp Realty

  3123 W Chase Ave, Chicago, IL 60645
• 

  

  /45

  $699,000

  • 6 Beds
  • 4 Baths

  5000 W Grace St, Chicago, IL 60641

  5000 W Grace is a welcoming brick multi-unit residence nestled on a sunny 29' wide south facing corner lot in prime Portage Park. A spacious 3-flat brick building, it boasts two vintage 2 bed/1 bath units each with large living rooms, dining rooms, updated bathrooms, sun porches, and hardwood floors. The in-law basement suite has 2bd/1ba and updated kitchen. This classic vintage Chicago building

  Katherine Paris Compass

  5000 W Grace St, Chicago, IL 60641
• 

  

  /28

  $565,000

  • 5 Beds
  • 3 Baths

  5253 W Cullom Ave, Chicago, IL 60641

  Expansive, updated 2-flat on oversized lot with modern kitchens and baths and versatile living options. The spacious top-floor unit features 3 bedrooms + den-ideal for strong rental income. The main-floor unit offers 2 bedrooms + den and space to offer 3rd bedroom. Option to maximize rent with duplex down or create an in-law suite in the basement. Solid building with lots of newer updates: Garage

  Trisha Kannon Coldwell Banker Realty

  5253 W Cullom Ave, Chicago, IL 60641
• 

  

  /21

  $900,000

  • 5 Beds
  • 3 Baths

  3621 N Ravenswood Ave, Chicago, IL 60613

  *Seller has VA loan which may be assumable.* This beautifully maintained, solid brick 2-flat in the highly desirable Lakeview neighborhood is as turn-key as they come-perfect for investors or owner-occupants alike. Nestled on a beautiful tree-lined street within the coveted Hamilton School District, this building combines timeless vintage character with modern updates. Original charm abounds

  Sarah Ahmed @properties Christie's International Real Estate

  3621 N Ravenswood Ave, Chicago, IL 60613
• 

  

  /58

  $779,900

  • 7 Beds
  • 3 Baths

  4143 W Roscoe St, Chicago, IL 60641

  HERE IT IS! Spacious Legal 2-Unit in Desirable Old Irving Park - Perfect for House Hackers or Investors! This well-maintained property offers modern updates, income potential, and a prime location on a quiet tree-lined street. The first-floor unit features 3 bedrooms, 1 bath, hardwood floors in three rooms, luxury vinyl plank flooring in the other two rooms and kitchen, central air conditioning

  Josh Reighard Baird & Warner

  4143 W Roscoe St, Chicago, IL 60641
• 

  

  /3

  $335,700

  • 9 Beds
  • 3 Baths

  4016 W Grenshaw St, Chicago, IL 60624

  Investment opportunity in North Lawndale! This multi-family property at 4016 W Crenshaw Street is being offered AS IS with tremendous upside potential. Currently fully occupied with established rental income and separate utilities in each unit. Conveniently located near public transportation including CTA trains and bus lines for easy commuting throughout Chicago. This well-positioned property

  Marquita Hollins Keller Williams Preferred Realty

  4016 W Grenshaw St, Chicago, IL 60624
• 

  

  /46

  $1,350,000 Open Sat 11AM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  2425 W Erie St, Chicago, IL 60612

  Welcome to this exceptional nearly 4,000 sq ft modern residence, where thoughtful upgrades redefine luxury city living! Situated in Ukrainian Village, this custom home offers every amenity imaginable-inside and out! Step into a sun-drenched floor plan with hardwood floors throughout (5 years old), and soaring ceilings that give way to meticulously designed spaces on every level. A true

  Victoria Mullins Haus & Boden, Ltd.

  2425 W Erie St, Chicago, IL 60612
• 

  

  /21

  $335,000

  • 5 Beds
  • 4 Baths
  • 2,523 Sq Ft

  7319 S Green St, Chicago, IL 60621

  Just listed!!! Luxury with lots of space, open concept, this newly gutted rehab 5 bedrooms, 4 full bathrooms, brand new 2 car garage, kitchen features 42 inch euro gloss white cabinets, stainless steel appliances, Beautiful polished porcelain floor tile on the main level, bathrooms and basement, hardwood floors in all bedrooms, modern ceiling fans, 1 electric fireplaces, Primary has its own bath,

  Donna Baker Kale Realty

  7319 S Green St, Chicago, IL 60621
• 

  

  /19

  $939,000

  • 9 Beds
  • 6 Baths

  4435 S Prairie Ave, Chicago, IL 60653

  Bronzeville newer construction investment property in vibrant neighborhood bustling with development. 7.9 Cap Rate and great opportunity for owner occupant. This exceptional three-flat building features spacious layouts with rear outdoor space and 3-car garage parking. Each of the three units offers **3 bedrooms and 2 baths**, boasting crisp, modern design and luxurious finishes throughout.

  Karen Biazar North Clybourn Group, Inc.

  4435 S Prairie Ave, Chicago, IL 60653
• 

  

  /31

  $1,500,000

  • 5 Beds
  • 5 Baths
  • 3,600 Sq Ft

  855 W Fullerton Pkwy, Chicago, IL 60614

  Say hello to 855 W Fullerton, a single family landmark rowhome in Lincoln Park's Seminary Townhome Association...an architecturally significant home in the McCormick Row House District built in 1884. This rarely available 5 bedroom, 4.5 bath home boasts almost 4000 square feet across 4 levels. This home is unmatched by anything on the market today. The absolutely breathtaking vintage

  Molly Marino Baird & Warner

  855 W Fullerton Pkwy, Chicago, IL 60614
• 

  

  /30

  $324,900

  • 5 Beds
  • 2 Baths
  • 2,972 Sq Ft

  1318 N Menard Ave, Chicago, IL 60651

  Welcome to this spacious 5-bedroom, 2-bathroom gem in the heart of North Austin! With nearly 3,000 square feet of living space, this home offers room for everyone. Ideally located just west of Central Ave and south of North Ave, you'll enjoy easy access to public transportation, shopping, parks, and more. Step inside to find gleaming hardwood floors throughout the main level, a generous kitchen

  Daniel DePaepe Baird & Warner

  1318 N Menard Ave, Chicago, IL 60651
• 

  

  /11

  $375,000

  • 5 Beds
  • 3 Baths

  Unlisted Address

  Don't miss this beautifully rehabbed 2-unit brownstone in the West Englewood area-perfect as an investment opportunity or owner-occupied home! Each unit offers updated kitchens with pantry storage, enclosed back porches ideal for entertaining, and a spacious fenced backyard ready for gardening, grilling, or family fun. Bring your most selective buyers-this property won't disappoint! Features:

  Jimmy Oliver Priority Plus Realty

  Unlisted Address
• 

  

  /47

  $1,199,900

  • 5 Beds
  • 4 Baths

  1100 W Wellington Ave, Chicago, IL 60657

  Don't miss this rare opportunity to own a beautifully maintained 3-unit building in the heart of Lakeview, ideally situated on a serene, tree-lined block. Owned and lovingly cared for by the same owner since 1984, this charming Victorian-style property offers timeless character, income potential, and versatile living options. The spacious owner's duplex-up that lives like a single-family home

  Jeanine McShea @properties Christie's International Real Estate

  1100 W Wellington Ave, Chicago, IL 60657
• 

  

  /16

  $419,900

  • 9 Beds
  • 3 Baths

  4936 S Loomis St, Chicago, IL 60608

  Solid brick 3-unit building featuring three spacious apartments, each with 3 bedrooms and 1 bath. All units are equipped with newer windows, in-unit laundry, maple cabinets, and granite countertops. Two units are currently occupied, providing immediate rental income. A great investment opportunity with strong potential!

  Jaime Birks eXp Realty

  4936 S Loomis St, Chicago, IL 60608
• 

  

  /17

  $325,000

  • 6 Beds
  • 2 Baths

  744 N Long Ave, Chicago, IL 60644

  This 2-unit property in the Austin neighborhood offers a great opportunity for buyers looking to customize a home to their vision. The property features generous space with both an attic and basement that provide potential to expand the current living areas on the top and bottom floors. Each unit has a solid layout, giving you a strong foundation to re-imagine and modernize. Perfect for an

  Asya Muhammad Coldwell Banker Realty

  744 N Long Ave, Chicago, IL 60644
• 

  

  /42

  $3,200,000

  • 6 Beds
  • 6 Baths
  • 5,000 Sq Ft

  1625 N Burling St Unit 401, Chicago, IL 60614

  One of a kind light-filled Lincoln Park duplex penthouse. Private elevator entrance brings you to this top floor hidden gem featuring 6 bedrooms, 6 bathrooms and 3 outdoor spaces including an expansive 1200 square foot deck with magnificent City & Sunset views. This boutique building in the most exclusive section of Lincoln Park is minutes from everything you'd want in Chicago, designed by

  Seth Captain Captain Realty LLC

  1625 N Burling St Unit 401, Chicago, IL 60614
• 

  

  /25

  $399,900

  • 5 Beds
  • 3 Baths

  5435 W Melrose St, Chicago, IL 60641

  For safety reasons the water and gas are off and should not be turned on. Welcome to this very large 5-bedroom 3-bathroom brick bungalow that is in need of your ideas and repair. The large bay window in the front of the home allows for lots of natural light and the classic hardwood floors, rich wood doors and 2 kitchens give you an idea of the home's potential! There is also a large garage which

  Vicki Vranas Berkshire Hathaway HomeServices Chicago

  5435 W Melrose St, Chicago, IL 60641
• 

  

  /39

  $699,900

  • 8 Beds
  • 7 Baths

  6527 S Drexel Ave, Chicago, IL 60637

  Beautiful 3 unit building, in the heart of Woodlawn. (2) 2bd/2bth and (1) DUPLEX with 4bd/3bth. Completed in 2008, this building has been well maintained. New decks installed 2022, primed and re-painted 2025, tuck pointed and sealed 2025, new stairwell carpet and paint 2025, New water heaters in each unit and more! Full list of improvements available. Premier block in Woodlawn, minutes from

  Jaki Harding Berkshire Hathaway HomeServices Starck Real Estate

  6527 S Drexel Ave, Chicago, IL 60637
• 

  

  /15

  $285,000

  • 6 Beds
  • 2 Baths

  8329 S Burnham Ave, Chicago, IL 60617

  Solid South Chicago 2-Flat Spacious bedrooms + eat-in kitchens big enough for a dining table! Super dry basement w/ coin laundry & tenant storage, plus enclosed back porch for totes/holiday decor. CHA voucher tenants in place (both planning to move), with rents currently low-huge upside for an investor ready to raise them! Systems serviced this year + roof in great shape. Off-street parking pad

  chequita dobson Coldwell Banker Realty

  8329 S Burnham Ave, Chicago, IL 60617
• 

  

  /25

  $449,900

  • 6 Beds
  • 2 Baths

  5092 W Monroe St, Chicago, IL 60644

  Located in the vibrant Austin neighborhood of Chicago, this 2-unit property is an excellent opportunity for investors or owner-occupants. Each unit features 3 spacious bedrooms and 2 full bathrooms, with beautiful hardwood floors throughout. The kitchens and bathrooms have been recently remodeled, showcasing modern finishes that add a touch of elegance to the space. A full unfinished basement

  Loreal Urso Baird & Warner

  5092 W Monroe St, Chicago, IL 60644
• 

  

  /25

  $559,000

  • 6 Beds
  • 3 Baths

  2536 N Austin Ave, Chicago, IL 60639

  Welcome to this beautifully maintained, all-brick two-unit building in Chicago's desirable Belmont Cragin neighborhood. Whether you're an investor seeking steady rental income or looking for the perfect space for multi-generational living, this versatile property checks all the boxes. Step inside to discover two bright and spacious units, each featuring generous living areas, modern finishes, and

  Roberta Ruiz Baird & Warner, Inc.

  2536 N Austin Ave, Chicago, IL 60639
• 

  

  /31

  $799,000

  • 6 Beds
  • 3 Baths

  4742 N Kedvale Ave, Chicago, IL 60630

  Incredible opportunity to own a fully rehabbed two-flat in the heart of Mayfair! No detail overlooked, featuring hardwood floors, abundant natural light, and open-concept living. Brand-new kitchens with quartz countertops, breakfast bars, and stainless-steel appliances. Modern bathrooms with stylish fixtures and finishes. The duplex-down (rented for $3,000/month) offers 4 beds, 2 baths with

  Kelsey Mayher Jameson Sotheby's Intl Realty

  4742 N Kedvale Ave, Chicago, IL 60630
• 

  

  /25

  $1,025,000

  • 12 Beds
  • 4 Baths

  4621 N Monticello Ave, Chicago, IL 60625

  Jumbo Brick 3-Flat plus Garden unit in red hot Albany Park! All four apartments are 3 bedroom/1 bath and have been recently rehabbed. The top three apartments all feature spacious kitchens, updated bathrooms and beautifully refinished hardwood floors throughout the extra-large living room & sunroom, formal dining room and big bedrooms. 1st floor kitchen has newer cabinets with granite

  Dale Todd Core Realty & Investments Inc.

  4621 N Monticello Ave, Chicago, IL 60625
• 

  

  /22

  $179,900

  • 5 Beds
  • 2 Baths

  2244 S Drake Ave, Chicago, IL 60623

  GREAT INVESTMENT OPPORTUNITY FOR THE SAVVY INVESTOR SOLD IN "AS IS" CONDITION, NO REPAIR CREDIT OFFERED, NO SURVEY OR TERMITE INSPECTION, TAX PRORATIONS 100%, BUYER TO VERIFY ROOM COUNT AND ALL SQ FOOTAGE. PROOF OF FUNDING/PRE-APPROVAL LETTER MUST ACCOMPANY ALL OFFERS.

  Emelin Brown Realty of America, LLC

  2244 S Drake Ave, Chicago, IL 60623
• 

  

  /21

  $520,000

  • 5 Beds
  • 2 Baths

  4829 S Champlain Ave, Chicago, IL 60615

  Discover this custom-style brick Georgian two-flat nestled in the heart of historic Bronzeville, Chicago. This well-maintained property features a two-bedroom, one-bath unit on the first floor and a spacious three-bedroom, one-bath unit on the second floor-perfect for investors or owner-occupants seeking rental income. Each unit showcases timeless architectural details, sun-filled living spaces,

  Omor Eguasa Baird & Warner

  4829 S Champlain Ave, Chicago, IL 60615
• 

  

  /44

  $859,900 Open Sat 11AM - 12:30PM

  • 7 Beds
  • 3 Baths

  4624 N Springfield Ave, Chicago, IL 60625

  Be captivated by this move-in ready, vacant prime Albany Park 3-flat-a rare investment opportunity! This renovated legal 3-flat is a true gem located on a charming tree-lined street in Albany Park, a vibrant neighborhood celebrated for its cultural diversity, thriving local dining scene, walkable streets, and convenient access to top-rated schools, parks, and public transit. Unit 1 and Unit 2

  Maria DelBoccio @properties Christie's International Real Estate

  4624 N Springfield Ave, Chicago, IL 60625
• 

  

  /14

  $365,000

  • 7 Beds
  • 3 Baths

  7100 S Prairie Ave, Chicago, IL 60619

  Great "live in" investment opportunity! This sturdy structured 2unit, features a duplex down from the 1st floor to the basement. The duplex unit has 4beds 2baths and the 2nd floor unit has 3beds 1bath. Located 3 blocks from the express way and surrounded by public transportation.

  Perdure Carter Realty of America, LLC

  7100 S Prairie Ave, Chicago, IL 60619
• 

  

  /26

  $325,000

  • 5 Beds
  • 2 Baths

  2345 S Lawndale Ave, Chicago, IL 60623

  Charming brick two unit building on an extra wide lot in the heart of vibrant Little Village! The building, built in 1875, features 2 stylishly updated apartments. Unit 1 is a 3 bedroom 1 bath with a huge kitchen, stainless steel Whirlpool appliances, granite countertops, blue cabinets, and plenty of space for a dining table or floating island. New wood laminate flooring throughout the spacious

  Kat Barry Compass

  2345 S Lawndale Ave, Chicago, IL 60623
• 

  

  /17

  $539,000

  • 10 Beds
  • 4 Baths

  5310 S Wolcott Ave, Chicago, IL 60609

  Beautifully 2025 Remodeled 3-Unit Investment Property in great Location! A Rare Opportunity to own a Brick triplex ideal for investors, owner-occupants, or multi-generational living. Unit 3, duplexed up features 4 beds/1.5 bath with 2 living areas, new kitchens (quartz countertops, stainless steel appliances, In unit Washer/Dryer (installed before closing)), new plumbing, new electric, new

  Ali Sana HomeSmart Realty Group

  5310 S Wolcott Ave, Chicago, IL 60609
• 

  

  /10

  $298,000

  • 8 Beds
  • 3 Baths

  7514 S Dante Ave, Chicago, IL 60619

  Discover this updated 2023 multi-unit property that blends style, convenience, and income potential. Featuring beautiful hardwood floors throughout, this building offers two tenant-occupied units for immediate rental income, while the 1st floor unit will be delivered vacant prior to closing making this ideal for an owner-occupant. Located in a prime area near a new clinic, shopping, and

  Tom Sweeney Baird & Warner

  7514 S Dante Ave, Chicago, IL 60619
• 

  

  /29

  $524,900 Open Sat 12PM - 2PM

  • 5 Beds
  • 4 Baths

  3159 W Washington Blvd, Chicago, IL 60612

  Welcome to 3159 W Washington Blvd-a virtually turnkey, two-flat built in 2007 that blends modern convenience with classic Chicago charm. The ground-floor unit welcomes you with gleaming hardwood floors, two spacious bedrooms, and a well-appointed bath. Upstairs, your duplex retreat boasts soaring ceilings, skylights flooding the open living space with natural light, three generous bedrooms, and

  Sohail Salahuddin eXp Realty

  3159 W Washington Blvd, Chicago, IL 60612
• 

  

  /38

  $495,100

  • 6 Beds
  • 3 Baths

  6424 S Richmond St, Chicago, IL 60629

  MARVELOUS AND ABSOLUTELY STUNNING RENOVATION ON THIS NEWLY TUCKPOINTED BRICK 2-UNIT IN CHICAGO LAWN. MAKE THIS YOUR HOME FOR FINANCIAL INTEGRITY WITH 3 BEDROOMS IN EACH UNIT AND SEPARATE UTILITIES. STEP INTO LUXURY WITH ULTRA MODERN FINISHES AND NEW OPEN CONCEPT DINING AND ISLAND KITCHEN ADORNED WITH WAINSCOTTING AND ENGINEERED WOOD LAMINATE FLOORING. NEW HIGH- END STAINLESS STEEL APPLIANCES:

  James Bohannon Enterprise Realty Power Broker

  6424 S Richmond St, Chicago, IL 60629
• 

  

  /46

  $1,695,000 Open Sun 11AM - 1PM

  • 7 Beds
  • 6 Baths

  2528 N Fairfield Ave, Chicago, IL 60647

  Architecturally Striking & Fully Renovated Three-Flat in Prime Logan Square! This is not your average multi-family. Welcome to an amazing full renovation of a legal 3-unit building that perfectly blends modern design with architectural character in the heart of Logan Square. Every detail has been meticulously crafted, showcasing style and quality from top to bottom. The owner's residence spans

  Daniel Merrion Coldwell Banker Realty

  2528 N Fairfield Ave, Chicago, IL 60647

Showing Results 201 - 240, Page 6 of 18