Homes for Sale in Chicago, IL with 5-Bedrooms

• 

  

  

  /17

  $470,999

  $24K PRICE DROP

  • 12 Beds
  • 6 Baths

  5718 S Green St, Chicago, IL 60621

  Beautiful grey stone rarely available , this is a great investment, 4 large unit , new roof , property in good shape and ready to move in with a little elbow grease, tall full basement , all individual heat back yard parking available , front units was made into SRO but can be easily de-convert ,great location , walk to Kennedy king college , just off the i 94 new electrical panel , some new

  Leroy Viamille Mills Realty Inc

  5718 S Green St, Chicago, IL 60621
• 

  

  

  /51

  $1,199,000

  • 9 Beds
  • 7 Baths

  1013 W 18th Place, Chicago, IL 60608

  Rare 2023 Gut-Renovated Compound in the Heart of Pilsen! This stunning three-unit property offers a sophisticated "house-hack" or high-yield investment opportunity just steps from the coveted 18th Street corridor. The expansive front residence lives like a luxury single-family home, boasting an open-concept 4BR/3BA floor plan anchored by a Chef's kitchen with quartz counters, custom backsplash,

  Salvador Gonzalez RE/MAX Mi Casa

  1013 W 18th Place, Chicago, IL 60608
• 

  

  

  /12

  $395,000

  • 6 Beds
  • 2 Baths

  5518 S Wood St, Chicago, IL 60636

  Income Producing 2 Unit in Prime Chicago Location. Fantastic investment opportunity! This solid brick 2 unit building offers huge 3 bedroom layouts in both units, each featuring hardwood floors, newer windows, and enclosed back porches for added storage and year-round usability. Inside, the units offer generous living and dining spaces with great natural light, tall ceilings, and classic Chicago

  Emily Roman Realty of America, LLC

  5518 S Wood St, Chicago, IL 60636
• 

  

  

  /22

  $265,000

  $70K PRICE INCREASE

  • 5 Beds
  • 2 Baths

  727 N Springfield Ave, Chicago, IL 60624

  Two Brick Flat in Humboldt Park 1/2 block from Chicago Ave. 3 electric meters, Circuit breakers. Cooper water pipes. 2 car garage. Front and rear fences. Quick access to Down Town via Pulaski to I-290 or via Chicago Ave and/or Grand Ave. To Be Sold in As-Is Condition. To be sold with City Code Violations.

  Maria Jerusalimiec Inter-City Realty, Inc.

  727 N Springfield Ave, Chicago, IL 60624
• 

  

  

  /18

  $139,000

  • 5 Beds
  • 3 Baths
  • 1,300 Sq Ft

  12908 S Wallace St, Chicago, IL 60628

  INVESTOR/HANDYMAN SPECIAL! BRICK CAPE COD ON A BEAUTIFUL BLOCK OF WEST PULLMAN IN A FANTASTIC POCKET! 3 FLOORS OF LIVING SPACE WITH A BATH ON EACH FLOOR! HARDWOOD FLOORS! CORP. OWNED, AS-IS SALE, CASH ONLY, NO SURVEY, TAXES 100%. EASY SHOW AND SELL!

  Ryan Cherney Circle One Realty

  12908 S Wallace St, Chicago, IL 60628
• 

  

  /10

  $159,900

  Pending

  • 6 Beds
  • 2 Baths

  8733 S Buffalo Ave, Chicago, IL 60617

  This two-flat property located at 8733 Buffalo presents a fantastic investment opportunity for those looking to capitalize on its income potential. Each unit consists of three spacious bedrooms and one bathroom, making it an ideal setup for families or renters seeking comfortable living spaces.This is not just a two flat; it's a canvas ready for your vision. Whether you're looking to invest or

  Daryl Molden Kale Realty

  8733 S Buffalo Ave, Chicago, IL 60617
• 

  

  /9

  $290,000

  Pending

  • 5 Beds
  • 2 Baths

  2720 W Flournoy St, Chicago, IL 60612

  Welcome to this classic two-Flat....with full basement just waiting to be converted into an in-law unit. Located on a quiet, tree-lined street with new construction all around. This well-maintained building offers two spacious units; one 3bdrm unit and one 2bdrm unit. Perfect for owner-occupants or investors, each unit features separate utilities. Major updates included newer roof, hot water

  Shirley Fields Coldwell Banker Realty

  2720 W Flournoy St, Chicago, IL 60612
• 

  

  /30

  $399,999

  • 8 Beds
  • 3 Baths

  7813 S East End Ave, Chicago, IL 60649

  Welcome to 7813 S East End Ave, a well-maintained solid brick 2-flat located in the heart of South Shore, just minutes from the lakefront and approximately 3 miles from the Obama Presidential Center. This property features two spacious 3-bedroom units with separate utilities, making it an ideal opportunity for both investors and owner-occupants. Each unit showcases hardwood floors throughout,

  Joshua Mercer Premier Chicago Real Estate

  7813 S East End Ave, Chicago, IL 60649
• 

  /2

  $2,000,000

  New Construction Pending

  • 5 Beds
  • 6 Baths
  • 4,100 Sq Ft

  2127 W Huron St, Chicago, IL 60612

  New construction , photo of previous build.

  Kevin Bigoness Baird & Warner

  2127 W Huron St, Chicago, IL 60612
• 

  

  /20

  $499,000

  Pending

  • 12 Beds
  • 4 Baths

  5436 W Jackson Blvd, Chicago, IL 60644

  Rarely available Austin 4-flat with strong income potential and substantial capital improvements throughout the years. Property appraised at $500,000 in July 2023. Recent unit updates include a 2025 rehab of Unit 1E and a 2022 rehab of Unit 1W. Major building improvements include a rubber roof installed on both the building and garage in 2015, with maintenance touch-ups completed in 2021, and a

  Debra Taitel Baird & Warner

  5436 W Jackson Blvd, Chicago, IL 60644
• 

  

  /26

  $599,900

  Pending

  • 6 Beds
  • 3 Baths

  5700 W Melrose St, Chicago, IL 60634

  Excellent opportunity to own a well-maintained two-flat offering flexible living arrangements. Largely renovated in 2012, the property has been meticulously cared for and provides multiple options for both owner-occupants and investors. The top-floor unit can function as a comfortable two-bedroom apartment. The main-level unit features two bedrooms, a remodeled kitchen, beautiful hardwood floors,

  Rafal Szypcio Coldwell Banker Real Estate Group

  5700 W Melrose St, Chicago, IL 60634
• 

  

  /45

  $1,350,000

  $255K PRICE INCREASE

  • 5 Beds
  • 5 Baths

  958 N Honore St, Chicago, IL 60622

  Presenting an exceptional opportunity to own a meticulously-maintained, classic brick 4-unit building in the heart of one of Chicago's most coveted neighborhoods - East Ukrainian Village. Positioned at the prime corner of Augusta and Honore, this property is surrounded by new development and multi-million-dollar homes, offering easy access to the city's finest dining, shopping, and transportation

  Qizhong Guan Century 21 S.G.R., Inc.

  958 N Honore St, Chicago, IL 60622
• 

  

  /45

  $294,900

  $5K PRICE DROP Pending

  • 5 Beds
  • 3 Baths
  • 1,458 Sq Ft

  10235 S Rhodes Ave, Chicago, IL 60628

  Presenting a distinguished fully updated 5-bedroom, 3-bathroom residence that exemplifies contemporary living. Upon entering, you are welcomed by an inviting ambiance that flawlessly integrates modern luxury with timeless charm. The home is appointed with sophisticated fixtures and finishes, including hard wood flooring throughout the 1st and 2nd living areas, providing both elegance and comfort.

  Bruno Styrczula First Midwest Realty LLC

  10235 S Rhodes Ave, Chicago, IL 60628
• 

  

  /22

  $379,000

  • 6 Beds
  • 2 Baths

  5737 S Laflin St, Chicago, IL 60636

  Welcome to this well - maintained 2-unit property, perfect for a first-time homebuyer or savvy investor! Each unit features 3 spacious bedrooms and 1 full bathroom. The property underwent renovations in 2024, including a brand-new kitchen with granite countertops. Enjoy year-round comfort with the added forced air with A/C on both floors and in-unit laundry already installed in both units. All

  Silvia Tenesaca Cloud Gate Realty LLC

  5737 S Laflin St, Chicago, IL 60636
• 

  

  /26

  $211,111

  Pending

  • 5 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  11361 S Racine Ave, Chicago, IL 60643

  Multiple offers received, highest and best offer due tonight at 9pm. Beautifully rehabbed 5-bedroom, 1.5-bathroom home, fully updated in 2026, offering a spacious and functional layout ideal for a variety of living needs. The main level features 3 bedrooms, a comfortable living area, and a well-appointed kitchen with brand-new appliances and ample cabinet space. The living room is filled with

  Sonny Ruan Chi Real Estate Group LLC

  11361 S Racine Ave, Chicago, IL 60643
• 

  

  /13

  $345,000

  Pending

  • 5 Beds
  • 3 Baths

  7034 S Hermitage Ave, Chicago, IL 60636

  Great investment opportunity in Englewood! This well-maintained two-unit building features two spacious units, each offering 2 bedrooms and 1 bathroom. Both units have separate utilities and individual meters, providing convenience for owners and tenants. The finished basement, powered by electricity, offers additional living space and can function as a potential in-law suite or extended living

  Myiah Williams EXIT Strategy Realty

  7034 S Hermitage Ave, Chicago, IL 60636
• 

  

  /50

  $599,900

  $79K PRICE DROP Pending

  • 6 Beds
  • 4 Baths

  2713 S Crowell St, Chicago, IL 60608

  Two Homes, One Opportunity, Live, Rent, Prosper,2713 S Crowell St, Chicago, IL 60608, Move-In Ready 2-Flat located in the heart of Bridgeport, one of Chicago's most vibrant and fast-growing neighborhoods. The building stands out in the street. Step into this beautifully updated 2-flat, perfect for multi-generational living or as a turnkey investment opportunity. First Floor (2024 completed

  linda lin RE/MAX Suburban

  2713 S Crowell St, Chicago, IL 60608
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  /45

  $519,000

  $131K PRICE DROP

  • 6 Beds
  • 2 Baths

  6418 S Drexel Ave, Chicago, IL 60637

  Stunning Greystone two-flat in SIZZLING hot Woodlawn! This is an exceptional opportunity in one of Chicago's fastest-growing neighborhoods. This classic multi-unit property offers two spacious 3-bedroom residences with soaring ceilings, original woodwork, and beautiful vintage details, including decorative fireplaces and charming built-ins that showcase timeless character. The partially finished

  Eboni Tankersley Urban Oasis Realty LLC

  6418 S Drexel Ave, Chicago, IL 60637
• 

  

  /16

  $1,190,000

  • 7 Beds
  • 4 Baths

  1939 W Thomas St, Chicago, IL 60622

  Fantastic opportunity to own a fully rented 4 flat with value add possibilities in unbeatable Wicker Park location! Located on beautiful street in East Village Historical District, property is steps to Division St and all Wicker Park restaurants, shops and nightlife. Units are fully occupied and always easy to rent. Front units are 1 bed + den, 1 bath and rear units are 2 bed 1 bath. 2 car garage

  Brett Huelat CL3 Property Management

  1939 W Thomas St, Chicago, IL 60622
• 

  

  /14

  $775,000

  Pending

  • 8 Beds
  • 4 Baths

  608 S Oakley Blvd, Chicago, IL 60612

  Pleased to present this rare Quadplex opportunity built in 1919 in Tri-Taylor. All 4 units are 2 Bedrooms and 1 Bath. The majority of the units have been meticulously maintained, newer roof, and basement laundry. The units also have In unit central air and ac with large kitchens and bathrooms.

  David Szymanowski Sperry Van Ness

  608 S Oakley Blvd, Chicago, IL 60612
• 

  

  /20

  $450,000

  Pending

  • 5 Beds
  • 3 Baths

  2841 W 25th St, Chicago, IL 60623

  Excellent opportunity to own a spacious, income-producing two-unit brick building in the heart of South Lawndale (Little Village), Chicago. This well-maintained property offers over 2,300 square feet of living space across two generously sized units, making it ideal for an owner-occupant or an investor seeking strong rental income potential. Each unit features a functional layout with ample

  Shams POURIAN Realistic Realty LLC

  2841 W 25th St, Chicago, IL 60623
• 

  

  /32

  $575,000

  Pending

  • 5 Beds
  • 3 Baths

  843 W 34th Place, Chicago, IL 60608

  ***Multiple offers received - Please submit your highest and best offer by Wednesday, May 27th at 9:00AM*** Solid structure, two oversized units, a full basement, and a rare double lot with a side-load 2-car brick garage make this Bridgeport 2-flat an exceptional opportunity in one of Chicago's booming neighborhoods. Offering approximately 2,728 square feet above grade (not including the

  Thomas Domasik RE/MAX 10 in the Park

  843 W 34th Place, Chicago, IL 60608
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  /57

  $499,900

  $45K PRICE DROP

  • 6 Beds
  • 3 Baths

  5032 S Kolin Ave, Chicago, IL 60632

  Welcome to this beautiful brick 2 flat building. With 4 leves of living spaces perfect investment opportunity. Frist floor is 2 bedrooms 1 full bathroom and duplex to finished basement with one bedroom and a living room. second floor with beautiful hardwood floor and the whole apartment is being fresh painted . And full finished attic with one bedroom, living room, bathroom perfect for in Laws. 3

  Jose Aparicio New Hope Realty Group, Inc.

  5032 S Kolin Ave, Chicago, IL 60632
• 

  

  /43

  $694,000

  Open Sun 12PM - 2:30PM

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

  10459 S Troy St, Chicago, IL 60655

  A 1944 Cape Cod flawlessly reimagined in 2018, 10459 S. Troy is a stunning display of modern elegance, intentional design, and everlasting comfort. Situated proudly on a quiet corner lot in the highly sought after Mount Greenwood neighborhood, the standard for perfection is set from the moment you arrive. You'll instantly feel welcomed by the charm of the 25 foot wide front porch... the perfect

  Margaret Mulrenin Compass

  10459 S Troy St, Chicago, IL 60655
• 

  

  /11

  $344,999

  $5K PRICE DROP

  • 8 Beds
  • 2 Baths

  12148 S Eggleston Ave, Chicago, IL 60628

  Well-maintained brick 2-flat offering spacious layouts and thoughtful updates throughout. Each unit features updated kitchens and bathrooms, along with dedicated washer and dryer hookups for added convenience.The property includes a versatile oversized 20x30 space ideal for a primary bedroom, additional living area, or recreation room. Major components have been updated, including roof, siding,

  Kayshonna Straughter Blue Door Dave Inc

  12148 S Eggleston Ave, Chicago, IL 60628
• 

  

  /32

  $1,275,000

  Pending

  • 6 Beds
  • 3.5 Baths
  • 3,185 Sq Ft

  3927 N Paulina St, Chicago, IL 60613

  Located on a beautiful tree-lined street in the highly sought-after Southport Corridor neighborhood and within Blaine Elementary School district, this spacious single-family home offers incredible potential in a fantastic location. Completely rebuilt in 2000, the home features generous living spaces, high ceilings, abundant natural light, and offers incredible functionality and potential for its

  Eudice Fogel Compass

  3927 N Paulina St, Chicago, IL 60613
• 

  

  /35

  $286,900

  Pending

  • 6 Beds
  • 3 Baths
  • 2,656 Sq Ft

  5723 S Marshfield Ave, Chicago, IL 60636

  Fully rehabbed and move in ready home offering over 2,600 sq ft of finished living space! This spacious property features 6 potential bedrooms, 3 full bathrooms, a finished basement, and a flexible layout ideal for large households, related living, or work from home needs. The updated kitchen showcases modern cabinetry, quartz countertops, and stylish finishes, while the remodeled bathrooms and

  Jorge Villegas Real Broker LLC

  5723 S Marshfield Ave, Chicago, IL 60636
• 

  

  /26

  $55,000

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths

  10540 S Lafayette Ave, Chicago, IL 60628

  *Rehabber's Special* Multiunit building on a double lot. Perfect for rental income or a quick flip. Needs TLC and property is being sold as-is. No survey. Tax proration 100%. Easy access to the expressway and steps to public transportation.

  Keith Martin Kale Realty

  10540 S Lafayette Ave, Chicago, IL 60628
• 

  

  /6

  $760,000

  $10K PRICE DROP

  • 7 Beds
  • 5 Baths

  611 E 50th Place, Chicago, IL 60615

  Discover this distinguished greystone residence with period addition, gracefully situated on a generous double lot in the historic Bronzeville/Washington Park neighborhood. The property features two sun-filled units plus a charming one-bedroom garden-level apartment. The building underwent comprehensive renovation in the mid-1990s, with subsequent updates including roof replacement approximately

  Nickola Wells RE/MAX Premier Luxury Collection

  611 E 50th Place, Chicago, IL 60615
• 

  

  /41

  $329,999

  • 5 Beds
  • 3 Baths

  6748 S Wabash Ave, Chicago, IL 60637

  Welcome home to this fully renovated brick residence in Chicago, blending modern style with timeless appeal. Featuring 5 generously sized bedrooms and 3 updated bathrooms, this home provides abundant space for family, guests, and entertaining. Step inside to an inviting living room with an open-concept layout that flows seamlessly into a spacious dining area-perfect for memorable gatherings. The

  Brittany Strale Redfin Corporation

  6748 S Wabash Ave, Chicago, IL 60637
• 

  

  /23

  $567,000

  Pending

  • 5 Beds
  • 3 Baths

  5342 W Newport Ave, Chicago, IL 60641

  Rarely available, traditional two-unit brick building located in the highly sought-after Portage Park neighborhood, just half a block from Chopin Park and within walking distance to the vibrant Central and Belmont business district and the Portage Park Olympic Pool. This owner-occupied property offers an excellent opportunity for both homeowners and investors. Each of the main and second-floor

  Al Rodriguez RE/MAX City

  5342 W Newport Ave, Chicago, IL 60641
• 

  

  /54

  $5,500,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 6,200 Sq Ft

  180 E Pearson St Unit 3704-3705, Chicago, IL 60611

  Introducing the most spectacular 6200 square foot combination home at The Water Tower Residences. Experience refined single-family living in the sky at Chicago's premier luxury address. This extraordinary 5-bedroom (optional 6-bedroom), 5.1-bathroom home commands the building's most coveted eastern exposure, spanning both the northeast and southeast corners. The result: breathtaking, unobstructed

  Kathleen Malone Compass

  180 E Pearson St Unit 3704-3705, Chicago, IL 60611
• 

  

  /25

  $350,000

  Pending

  • 7 Beds
  • 4 Baths
  • 1,428 Sq Ft

  2825 N Moody Ave, Chicago, IL 60634

  Investors Dream - Single Family Residence turned into multiple living areas property. This property's unique set up comes from the previous century and is being carried to the present time. 2 levels of living space! First level has 4 bedrooms, 2 baths, and additional living space. Second level has 3 bedrooms, 2 baths, and separate heating system, hot water tank and electric meter. Property needs

  Anna Kawa arhome realty

  2825 N Moody Ave, Chicago, IL 60634
• 

  

  /23

  $449,000

  Pending

  • 7 Beds
  • 2 Baths

  5015 S Talman Ave, Chicago, IL 60632

  Great brick building with 2 very spacious apartments with 3 bedrooms, Huge kitchens, and office space. Finished attic and full spacious basement. Building has a new roof and many improvements.In the heart of Gage Park.It has hardwood floors, and vinyl throughout The bathrooms have soaker tubs and vanity lighting.. This is a great building with many different ways to convert or expand the

  Elisa Miller New Heritage Real Estate

  5015 S Talman Ave, Chicago, IL 60632
• 

  

  /27

  $420,000

  $69K PRICE DROP Pending

  • 9 Beds
  • 3 Baths

  1529 S Homan Ave, Chicago, IL 60623

  For Sale: Nicely maintained 3 unit building situated in Chicago's North Lawndale neighborhood. This spacious building has modern kitchens with stainless steel appliances and sleek tile bathrooms. The entire building is vacant, so it is ideal for an owner occupant or investor. Includes a concrete parking pad in the rear for 2 vehicles. Turn key/ ready to move in or rent immediately.

  Matthew Davis Kale Realty

  1529 S Homan Ave, Chicago, IL 60623
• 

  

  /71

  $1,499,900

  Pending

  • 5 Beds
  • 4.5 Baths
  • 4,350 Sq Ft

  6235 N Kedvale Ave, Chicago, IL 60646

  Elegant 95% New Construction in the Highly Desirable Sauganash Neighborhood! This exceptional 5-bedroom, 4.5-bath residence showcases refined luxury, impeccable craftsmanship, and thoughtful design throughout. From the moment you step inside, the home offers an immediate sense of warmth and sophistication, blending timeless elegance with modern comfort. Designed with an expansive open floor plan,

  Angela Hotca-Roos Berkshire Hathaway HomeServices Chicago

  6235 N Kedvale Ave, Chicago, IL 60646
• 

  

  /34

  $585,000

  Pending

  • 6 Beds
  • 3 Baths

  5935 W Patterson Ave, Chicago, IL 60634

  Welcome to this well maintained 2 flat. The Garden unit features 2 bed/1 bath and in unit laundry. The 2nd floor is duplex up and it features a dining/ living room area/ eat in kitchen / with in unit laundry as well. This duplex features 1 bed/1 Bath on the main level and 3 bed/ 1 additional bath on the 2nd floor. The backyard is massive with a nice size deck and 2 car garage. This building has

  Laura Rodriguez Realty of America, LLC

  5935 W Patterson Ave, Chicago, IL 60634
• 

  

  /32

  $975,000

  • 9 Beds
  • 5 Baths

  3579 W Mclean Ave, Chicago, IL 60647

  Turnkey 3-Flat | Full Gut Rehab | Logan Square / Palmer Square Rare opportunity to acquire a fully TRUE gut-rehabbed 3-flat in the heart of one of Chicago's most coveted Northwest Side neighborhoods. Completed in 2021, this top-to-bottom renovation was done right - with quality materials, long-term durability, and minimal deferred maintenance in mind. Not a cosmetic flip, but a true gut rehab

  Brian Mond 33 Realty

  3579 W Mclean Ave, Chicago, IL 60647
• 

  /2

  $5,250,000

  New Construction

  • 8 Beds
  • 7.5 Baths
  • 7,118 Sq Ft

  Chicago, IL 60657

  Amazing design/build opportunity in the Southport Corridor coming soon from Environs on a 37.5' lot and a half with a breezeway attachment to an attached 3 car garage with Mudroom! This 7,100 square foot, 8 BR, 7.5 BA home will feature a highly functional, unusually open layout and offers 4 BR suites on the 2nd level including an expansive Primary Suite. The third floor features a spacious 3rd

  Kevin Wood @properties Christie's International Real Estate

  Chicago, IL 60657
• 

  

  /38

  $949,900

  $50K PRICE DROP Pending

  • 6 Beds
  • 4 Baths

  4615 N Keystone Ave, Chicago, IL 60630

  Gorgeous 4 Flat Building in Albany Park offers a fantastic investment opportunity! The units include two - 2 bedroom, 1 full bath and two - 1 bedroom, 1 full bath and all units have a gorgeous screened in porch. One of the first floor units is vacant and is completely remodeled with a 4 season room! The Building also offers original beautiful wood molding throughout, 4 storage rooms available,

  Natalie O'Donnell Baird & Warner

  4615 N Keystone Ave, Chicago, IL 60630

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