Homes for Sale in Chicago, IL with 5-Bedrooms

• 

  

  

  /19

  $674,800

  • 6 Beds
  • 4 Baths
  • 3,900 Sq Ft

  5529 W Cornelia Ave, Chicago, IL 60641

  Welcome to this stunning, fully rehabbed single-family brick octagonal bungalow, where timeless architecture meets modern living. This beautifully updated home features six spacious bedrooms and four full bathrooms, offering ample room for comfortable living. The main level welcomes you with a bright, open-concept living and dining area, perfect for gatherings and everyday enjoyment. The updated

  Ryan Casper eXp Realty

  5529 W Cornelia Ave, Chicago, IL 60641
• 

  

  

  /22

  $575,000

  • 6 Beds
  • 3 Baths

  3749 S Union Ave, Chicago, IL 60609

  Welcome to this fantastic two-unit building situated on a highly desirable, wide street in the heart of the vibrant Bridgeport neighborhood!This well maintained property is perfect for both homeowners and savvy investors looking to capitalize on the thriving rental market. Unit 1, the owner's unit, is currently vacant, offering a blank canvas for new owners or tenants to personalize their space.

  Inga Aleksonis Keller Williams Preferred Rlty

  3749 S Union Ave, Chicago, IL 60609
• 

  

  

  /54

  $370,000

  • 6 Beds
  • 3 Baths

  6229 S Bishop St, Chicago, IL 60636

  Unlock steady income and long-term appreciation with this turnkey 2-unit building in Chicago's West Englewood neighborhood. Recently rehabbed, this property blends modern upgrades with historic charm, offering immediate rental potential or owner-occupancy. Situated on a quiet cul-de-sac, it's a peaceful haven with easy street parking. Unit 1: Spacious 3BR/2BA Duplex with Finished Basement (Ideal

  Juneitha Shambee Juneitha Shambee

  6229 S Bishop St, Chicago, IL 60636
• 

  

  

  /13

  $245,000

  • 6 Beds
  • 4 Baths

  7407 S Kenwood Ave, Chicago, IL 60619

  Classic brick 2-flat offering income, space, and long-term potential. Each unit features 3 bedrooms, 1.5 baths, and separate utilities with solid structure throughout. Great option for an owner occupant or anyone looking to start building wealth through real estate ownership.

  David Bovyn Chicago Style

  7407 S Kenwood Ave, Chicago, IL 60619
• 

  

  

  /9

  $299,000

  • 5 Beds
  • 2 Baths

  6959 S Calumet Ave, Chicago, IL 60637

  Brick 2-flat offering strong potential and a classic Chicago layout. Rehabbed in 2016, this property features a 2-bed/1-bath unit on the first floor and a 3-bed/1-bath unit upstairs-each with separate utilities and gas heat. Great fit for an owner-occupant or anyone looking to expand their portfolio.

  David Bovyn Chicago Style

  6959 S Calumet Ave, Chicago, IL 60637
• 

  

  /9

  $340,000

  • 6 Beds
  • 2 Baths

  4429 W Adams St, Chicago, IL 60624

  Calling all savvy investors and visionary homeowners! This historic three-story brick multi-family building (circa 1900) at 4429 W. Adams St offers the perfect canvas for your next high-yield project. Situated in the heart of West Garfield Park, this property combines vintage architectural character with the expansive square footage required for modern, high-demand rental units.

  Lucretia Martin Chicago Style Management LLC

  4429 W Adams St, Chicago, IL 60624
• 

  

  /21

  $94,900

  • 5 Beds
  • 2 Baths
  • 2,300 Sq Ft

  11920 S Calumet Ave, Chicago, IL 60628

  INCREDIBLE INVESTMENT OPPORTUNITY - TWO HOMES FOR THE PRICE OF ONE! Situated on two oversized lots, this unique property offers exceptional potential for investors, rehabbers, or buyers looking to build equity. The property includes two separate houses plus a spacious 3-car garage, providing endless possibilities for renovation, rental income, or redevelopment. Both homes require a complete

  Ernesto Camarillo Century 21 Universal

  11920 S Calumet Ave, Chicago, IL 60628
• 

  

  /15

  $270,000

  • 7 Beds
  • 2 Baths

  7614 S Maryland Ave, Chicago, IL 60619

  Discover this solid, well-maintained brick two-flat that perfectly blends vintage Chicago charm with modern investment potential. Whether you are looking for an owner-occupant "house-hack" or a reliable passive income stream, 7614 S. Maryland Ave is a standout choice in a high-demand rental corridor.

  Lucretia Martin Chicago Style Management LLC

  7614 S Maryland Ave, Chicago, IL 60619
• 

  

  /23

  $349,900

  • 7 Beds
  • 3.5 Baths
  • 1,200 Sq Ft

  1509 W 72nd Place, Chicago, IL 60636

  This stunning 7-bedroom, 3.5-bathroom home offers a large layout across three finished levels. The main floor features an open living area, crown molding, and a neutral color palette. The kitchen includes white shaker cabinets, quartz countertops, a charcoal subway tile backsplash, and a stainless steel appliance package. This level contains 3 bedrooms and a full bathroom with custom tile work.

  Monica Villarreal Baird & Warner

  1509 W 72nd Place, Chicago, IL 60636
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  /56

  $2,300,000

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

  5415 N Ashland Ave, Chicago, IL 60640

  A rare private oasis in the heart of Andersonville, this extraordinary residence offers a level of resort-style living seldom found in Chicago. The expansive, beautifully landscaped backyard creates a secluded luxury retreat in the city, complete with a heated pool, spa, generous outdoor entertaining space, and a separate guest house for hosting friends or housing an au pair-an exceptional

  Emily Santos @properties Christie's International Real Estate

  5415 N Ashland Ave, Chicago, IL 60640
• 

  

  /48

  $385,000

  • 6 Beds
  • 3 Baths
  • 1,128 Sq Ft

  6616 S Kedvale Ave, Chicago, IL 60629

  2 Story brick home with 2 Bedrooms on main level 1 bath , high ceilings, 2 bedrooms on 2nd level 1 bath, full finished basement with extra 2 rooms, family room, 1 bath, has 2 furnaces, 2 a/c units, newer windows, newer roof, deck with roof top, 2 car garage, privacy fence. Close to Public transportation, Stores, Midway Airport. Pre-approved Buyers please.

  Mireya Rogoz-Bedore Village Realty, Inc.

  6616 S Kedvale Ave, Chicago, IL 60629
• 

  

  /14

  $1,200,000

  • 9 Beds
  • 6 Baths

  4906 S Saint Lawrence Ave, Chicago, IL 60615

  Welcome to 4906 S Saint Lawrence, a magazine-caliber, simply stunning building featuring extra-wide 1,600 sq ft units in this expansive newer construction three-flat. All units offer 3 bedrooms and 2 baths with exceptional elegance, intelligent design, professionally appointed kitchen cabinetry, integrated appliances, a quartz island, custom backsplash, engineered hardwood floors, and more.

  Michael Scanlon eXp Realty

  4906 S Saint Lawrence Ave, Chicago, IL 60615
• 

  

  /15

  $160,000

  • 5 Beds
  • 2 Baths
  • 970 Sq Ft

  6942 S Bell Ave, Chicago, IL 60636

  SERIOUS BUYERS ONLY!!! Short sale- 5 bed home with 2 baths. In need of TLC and updates. Purchase PRICE will be submitted and approved BY THE BANK PROPERTY SOLD AS IS!!! Roof done 5 years ago and tuck poing 3 years ago.

  Latonia Goldsmith Century 21 IMPACT

  6942 S Bell Ave, Chicago, IL 60636
• 

  

  /29

  $350,000

  • 6 Beds
  • 1.5 Baths
  • 2,204 Sq Ft

  3549 S Indiana Ave, Chicago, IL 60653

  THE BRONZEVILLE WEALTH-PIVOT: HISTORIC GREYSTONE WITH LEGAL 2-UNIT POTENTIAL. Positioned at the intersection of heritage and high-yield, 3549 S. Indiana is a rare, fully gutted Greystone shell with a new roof; zoned RM-5. This is a strategic opportunity to capitalize on the April 1, 2026, Citywide ADU Ordinance expansion, which allows for a legal 2-unit conversion (Luxury Owner's Double Duplex +

  Regina Stevenson Illinois Real Estate Partners

  3549 S Indiana Ave, Chicago, IL 60653
• 

  

  /19

  $369,000

  • 6 Beds
  • 3 Baths

  Unlisted Address

  Yellow brick 3 unit building with a 3 car brick garage! Yup!!! All brick. New tuck-pointing with new lentils. Perfect opportunity to own a low maintenance, cash-flowing, multi-unit building in Chatham. The building is fully stabilized and income generating.

  Yanira Doyle Century 21 IMPACT

  Unlisted Address
• 

  

  /14

  $264,000

  • 6 Beds
  • 2 Baths

  5419 S Hermitage Ave, Chicago, IL 60609

  Exceptional Investment Opportunity! Welcome to 5419 S Hermitage Avenue - a solid, income-generating two-flat with tremendous upside potential. Built in 1918 and brimming with classic Chicago character, this approximately 3,000 sq. ft. multi-family property sits on a 3,750 sq. ft. lot and delivers both immediate cash flow and long-term value. The main structure features two well-appointed

  Lori Wyatt Real Estate Growth Partners

  5419 S Hermitage Ave, Chicago, IL 60609
• 

  

  /31

  $1,200,000

  • 8 Beds
  • 10 Baths
  • 11,108 Sq Ft

  3736 S Michigan Ave, Chicago, IL 60653

  A mansion in Bronzeville, built in the 19th century for a leading grain dealer and later used as a Black-owned hospital, is on the market for the first time in three decades, sold by a woman who has carefully restored many of its ornate historical finishes.Take a look back into the 19th century with this architectural masterpiece. Located in Chicago's historic Bronzeville neighborhood, this

  Michael Giliano Compass

  3736 S Michigan Ave, Chicago, IL 60653
• 

  

  /47

  $649,900

  • 6 Beds
  • 4 Baths
  • 3,679 Sq Ft

  4912 W Drummond Place, Chicago, IL 60639

  Largest Bungalow in the area. Excellent layout with 4 decent size bedrooms on 2nd floor. Experience the perfect blend of timeless character and contemporary luxury in this masterfully rehabbed 6-bedroom, 4-bath home. Behind its sleek Hardie-board facade, discover an expansive, sun-drenched interior defined by the thoughtful craftsmanship of an attentive to detail builder. The main level welcomes

  Deborah Hess Compass

  4912 W Drummond Place, Chicago, IL 60639
• 

  

  /60

  $1,130,000

  • 9 Beds
  • 7 Baths

  8729 W Summerdale Ave, Chicago, IL 60656

  WOW! Click 3D Tour! Rare, Custom-Built Jumbo 3-Flat Near O'Hare! Over 8,500 Sq Ft of Living Space! Incredible opportunity to own a one-of-a-kind, oversized building featuring three huge 3-bedroom units plus a finished in-law garden unit. Meticulously maintained by long-time owners. Each unit is updated and includes a refrigerator, oven, dishwasher, and microwave. Perfect for an owner-occupant or

  Gregorio Cirone xr realty

  8729 W Summerdale Ave, Chicago, IL 60656
• 

  

  /20

  $630,000

  • 7 Beds
  • 3 Baths

  1852 W 17th St, Chicago, IL 60608

  Perfect Multi Unit opportunity located in the heart of Pilsen! One of Chicago's hottest neighborhoods in a desirable area! This building has been with the family for almost 60 years! This large building consists of 4 apartments and an unfinished attic that may possibly be duplexed. 1st floor has 2 apartments. 2nd floor apartment is spacious and long; it has 3 bedrooms a living rm, dinning rm and

  Elia Bonilla RE/MAX LOYALTY

  1852 W 17th St, Chicago, IL 60608
• 

  

  /15

  $366,000

  • 6 Beds
  • 3 Baths
  • 1,363 Sq Ft

  5839 S Sacramento Ave, Chicago, IL 60629

  Are you looking for a welcoming and spacious Chicago Bungalow to call home? Here is a 6-bedroom, three-level home with a bathroom on each floor. Full bath on the main level, half a bath in the dormer attic and a 3/4 bath in the fully finished walk-out basement. Main level boats 3 spacious bedrooms, each with closets; large living room with plenty of sunlit windows and walk into a flow-like

  Paz Martinez Realty 1-2-3, Inc.

  5839 S Sacramento Ave, Chicago, IL 60629
• 

  

  /31

  $1,649,000

  • 5 Beds
  • 3.5 Baths
  • 3,564 Sq Ft

  1201 E 56th St, Chicago, IL 60637

  Designed by the well-known Prairie School architects Tallmadge & Watson, this spectacular, light-filled family home, just steps from the University of Chicago campus, has been meticulously modernized while preserving a wealth of period detail, including Roman brick fireplaces, incredible oak and birch woodwork, and hardwood floors throughout. The stunning kitchen has been completely renovated and

  Robert Sullivan Berkshire Hathaway HomeServices Chicago

  1201 E 56th St, Chicago, IL 60637
• 

  

  /41

  $1,575,000

  • 7 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  5309 S Greenwood Ave, Chicago, IL 60615

  Nestled beneath the steep eaves of this enchanting residence are seven bedrooms and two full baths, offering an exceptional blend of historic character and modern practicality. Set on a large, professionally landscaped lot with a three-car garage, the Tudor-style home is just a short walk from the main campus of the University of Chicago. Designed in 1904 by the distinguished New York

  Susan O'Connor Berkshire Hathaway HomeServices Chicago

  5309 S Greenwood Ave, Chicago, IL 60615
• 

  

  /24

  $750,000

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

  4621 N Anthon Ave, Chicago, IL 60656

  It's so much bigger in person. Larger. Lighter. Lovelier than you expect from the photos. Step inside and you'll immediately see what makes this home special. A home this large rarely comes on the market in this charming Schorsch Village neighborhood. With more than 4,000 square feet of living space, five oversized bedrooms, and four full bathrooms, it feels bright, open, and endlessly spacious.

  Suzanne Earth Baird & Warner

  4621 N Anthon Ave, Chicago, IL 60656
• 

  

  /29

  $1,099,000

  • 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
• 

  

  /60

  $2,500,000

  • 6 Beds
  • 7 Baths
  • 12,000 Sq Ft

  2851 W Rascher Ave, Chicago, IL 60625

  WELCOME TO THE RASCHER MANSION. Situated in the highly sought-after northwest corner of Lincoln Square in Budlong Woods, this home is the epitome of chic urban living-a captivating destination for those in search of a true standout residence. Set on an expansive 120' x 125' lot (no alley gives home added 10' in depth) and offering approximately 12,000 sq ft of luxurious living space, the mansion

  Barbara O'Connor Baird & Warner

  2851 W Rascher Ave, Chicago, IL 60625
• 

  

  /22

  $1,830,000

  • 11 Beds
  • 11 Baths

  1017 S Claremont Ave, Chicago, IL 60612

  This stunning, newly constructed (2024) 3-unit multi-family building is located in the heart of Chicago's vibrant and rapidly growing Tri-Taylor neighborhood. The second and third floors each feature spacious, thoughtfully designed units with 3 generously sized bedrooms and 3 modern full bathrooms. The first-floor unit is a duplex that offers 2 bedrooms and 2 bathrooms on the main level,

  Sonny Ruan Chi Real Estate Group LLC

  1017 S Claremont Ave, Chicago, IL 60612
• 

  

  /62

  $949,000

  • 7 Beds
  • 4 Baths

  1501 W Wilson Ave, Chicago, IL 60640

  Set on a prominent corner lot in a truly special neighborhood, this charming Victorian has been held by the same family for generations-an increasingly rare find. Currently configured as three units, the property offers immediate scale and long-term upside for the right buyer with vision. The building's soul remains intact. Original ornate woodwork and period details still grace the interior,

  Matt Silver Corcoran Urban Real Estate

  1501 W Wilson Ave, Chicago, IL 60640
• 

  

  /30

  $790,000

  • 6 Beds
  • 2 Baths

  1814 N Sawyer Ave, Chicago, IL 60647

  Completely updated 2 unit building in Prime Logan Square on an expansive 25' x 177' oversized lot, Just steps away from the popular 606 Trail. Completely Rehabbed in 2018 with new electric, plumbing, a/c, heat, water heater, windows, exterior siding on house, porches, roof, elevator, kitchens, baths, in unit laundry and much more! First Floor unit features an open floor plan , hardwood floors

  Lisa Graziani Caporale Realty Group

  1814 N Sawyer Ave, Chicago, IL 60647
• 

  

  /9

  $125,000

  • 5 Beds
  • 4 Baths

  3024 E Cheltenham Place, Chicago, IL 60649

  Calling All Investors! Rare opportunity to own a luxury 2-flat just steps from the Thrive Exchange development on Chicago's South Side. Located just one block from Lake Michigan, this property sits in a rapidly appreciating area with strong rental and resale upside. Investment Highlights: Approved plans & permits in hand Opportunity to complete a high-end, income-producing asset Prime South Side

  Shavon Mitchell Blue Door Dave Inc

  3024 E Cheltenham Place, Chicago, IL 60649
• 

  

  /28

  $550,000

  • 7 Beds
  • 4 Baths

  934 W 35th Place, Chicago, IL 60609

  Central Bridgeport - Fully-Occupied Classic Chicago Brick 3-Flat on extra-deep lot. Great long-term tenants in updated apartments. Convenient location close to all shopping, public transportation, parks, and access to all expressways provides a steady stream of committed and appreciative tenants. Kitchens and Bathrooms all updated. This building is a great performer. Extra-deep lot and the

  Matt Shrake Coldwell Banker Real Estate Group

  934 W 35th Place, Chicago, IL 60609
• 

  

  /18

  $449,000

  • 9 Beds
  • 3 Baths

  652 W Garfield Blvd, Chicago, IL 60609

  This 3-unit brick building offers 3 bedrooms rooms on each floor with updated kitchens and 4th in law unit in the basement. The primary bedrooms are spacious retreats with ample natural light. There is additional space for expansion in the basement. The Bedrooms are well-proportioned and can accommodate a variety of living arrangements. The home features gleaming hardwood floors throughout, all

  Robert Reyes Realty of America, LLC

  652 W Garfield Blvd, Chicago, IL 60609
• 

  

  /34

  $824,999

  • 6 Beds
  • 3 Baths

  4519 N Troy St, Chicago, IL 60625

  Solid brick 2-unit building situated on an oversized lot, offering immediate income with exceptional long-term upside. Professionally managed and well cared for by a long-time owner, this is a true value-add opportunity in a classic Chicago multi-unit. The second-floor unit features 3 bedrooms and is leased through February 2027 to a long-time tenant, providing stable income from day one. The

  Tanya Orndorff Equity Partners Real Estate, LLC

  4519 N Troy St, Chicago, IL 60625
• 

  

  /22

  $290,000

  • 5 Beds
  • 3 Baths

  8411 S Elizabeth St, Chicago, IL 60620

  Solid brick 2-flat offering space, flexibility, and long-term upside. The first floor features 3 bedrooms and 1 bath, while the upper unit offers 2 bedrooms and 1 bath-both with separate utilities and classic Chicago charm. Strong bones, gas heat, and an unfinished basement provide a clean foundation for updates or expansion. Ideal for owner occupants or anyone looking to grow their portfolio

  David Bovyn Chicago Style

  8411 S Elizabeth St, Chicago, IL 60620
• 

  

  /23

  $304,900

  • 5 Beds
  • 2 Baths

  Unlisted Address

  This stunning home has undergone a complete renovation in 2026, featuring new siding, a roof, kitchen, flooring, paint, and railings. It boasts five bedrooms and two full bathrooms within a two-story structure. Additionally, there is a spacious unfinished basement brimming with potential. Enjoy a large backyard, perfect for gatherings with family and friends. Don't let this opportunity pass you

  Andres Olaez Keller Williams ONEChicago

  Unlisted Address
• 

  

  /21

  $359,000

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  3320 W 60th Place, Chicago, IL 60629

  A beautifully maintained single-family home nestled on a charming tree-lined street in Chicago Lawn. This sunlit, three-level residence features four bedrooms plus a fifth bedroom/den in the lower level, two full bathrooms, a half bathroom on the second floor, separate living and dining rooms, and a spacious eat-in kitchen with a pantry/closet. Enjoy the rear enclosed porch, full-sized washer and

  Armando Vargas Berkshire Hathaway HomeServices Chicago

  3320 W 60th Place, Chicago, IL 60629
• 

  

  /17

  $810,000

  • 8 Beds
  • 4 Baths

  3823 N Lavergne Ave, Chicago, IL 60641

  Solid brick 4-unit building located near Six Corners. Each unit is about 900 SF and features 2 bedrooms and 1 bathroom. Unfinished basement includes coin operated laundry machines. 3 car garage space is fully rented. Building was remodeled in 2011 and has been consistently maintained. Recent improvements include tuck-pointing on the west side, above second floor windows (2025), tuckpointing on

  Advije Ismaili AA Management, LLC

  3823 N Lavergne Ave, Chicago, IL 60641
• 

  

  /45

  $489,000

  • 6 Beds
  • 3 Baths

  2420 S Sawyer Ave, Chicago, IL 60623

  Solid brick, 3-unit building in a rapidly developing neighborhood, fully renovated in 2023 and completely move-in ready. Each unit features separate furnaces (2023), central A/C (2023), and in-unit washer/dryer (2023), offering independent utilities and modern convenience for tenants. Quality finishes and numerous recent upgrades make this a true turnkey, income-ready investment with minimal

  Yomaira Roman Herrera RE/MAX LOYALTY

  2420 S Sawyer Ave, Chicago, IL 60623
• 

  

  /27

  $1,295,000

  • 8 Beds
  • 4 Baths

  2832 N Mozart St, Chicago, IL 60618

  Discover this striking octagonal 4-unit building offering spacious 2-bedroom, 1-bathroom apartments in one of Chicago's most vibrant neighborhoods. Perfectly situated in Avondale-enjoy all the energy of nearby Logan Square without the higher taxes-this property combines distinctive architecture with impressive income potential. Each unit features generous layouts designed for comfortable living,

  Robert Reyes Realty of America, LLC

  2832 N Mozart St, Chicago, IL 60618
• 

  

  /37

  $415,000

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

  624 E 90th Place, Chicago, IL 60619

  AMAZING OPPORTUNITY TO OWN THIS ONE OF A KIND REHAB. INCREDIBLE CRAFTSMANSHIP THROUGHOUT THIS ENTIRE HOME THAT STARTS WITH THE BEAUTIFUL NEW 2ND FLOOR ADDITION. THIS AMAZING PROPERTY HAS 4+1 BEDROOMS AND 3.5 BATHS. THE ATTENTION TO DETAIL ON THIS PROPERTY IS UNMATCHED. THE MAIN FLOOR BOAST AN OPEN CONCEPT GREAT FOR ENTERTAINING, THE SECOND FLOOR HAS A VERY LARGE MASTER SUITE PLUS 2 MORE BEDROOMS

  Nick Pipala McSully Properties LLC

  624 E 90th Place, Chicago, IL 60619

Showing Results 441 - 480, Page 12 of 18