Homes for Sale in Chicago, IL with 5-Bedrooms

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  /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
• 

  

  

  /47

  $395,000

  Pending

  • 5 Beds
  • 2 Baths
  • 1,707 Sq Ft

  3041 S Kildare Ave, Chicago, IL 60623

  Rare opportunity to own one of the few homes currently available in the surrounding area. With very limited inventory nearby, this spacious and light-filled classic brick bungalow offers a unique chance for buyers seeking space, character, and flexible living. This beautifully maintained home features 5 bedrooms and 2 full bathrooms, combining the timeless charm of traditional bungalow

  Abiezer Molina Chicagoland Brokers, Inc.

  3041 S Kildare Ave, Chicago, IL 60623
• 

  

  

  /56

  $9,995,000

  • 10 Beds
  • 10 Baths
  • 13,400 Sq Ft

  2026 N Kenmore Ave, Chicago, IL 60614

  Unique opportunity for the luxury homeowner who wants to provide an opportunity for an extended family habitat, live in nanny, or even business associates to be close in the huge coach house over the attached 5 car garage. The coach house also could be a huge basketball court with not much effort. This outstanding renovation was customized to perfection by Soucie Horner for this current owner who

  Emily Sachs Wong @properties Christie's International Real Estate

  2026 N Kenmore Ave, Chicago, IL 60614
• 

  

  /16

  $49,900

  • 6 Beds
  • 2 Baths

  636 W 62nd St, Chicago, IL 60621

  TWO FLAT BUILDING IN THE HEART OF UP&COMMING ENGLEWOOD. The property needs rehab to bring it back to its former glory. Great layout. Hardwood floors throughout. Sold as is. No survey provided.

  David Williamson Choice Realty Group Inc.

  636 W 62nd St, Chicago, IL 60621
• 

  

  /25

  $289,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 2,185 Sq Ft

  2038 E 73rd St, Chicago, IL 60649

  Brick bungalow in South Shore with open concept layout, newly renovated eat-in kitchen, three spacious bedrooms, bonus room, and versatile third floor. Unfinished basement for expansion and a newly installed backyard fence for outdoor entertaining. Convenient location near Lakefront, Jackson Park, Museum of Science and Industry, Rainbow Beach, grocery stores, and public transportation.

  Laura Rodriguez Realty of America, LLC

  2038 E 73rd St, Chicago, IL 60649
• 

  

  /7

  $409,900

  Pending

  • 10 Beds
  • 3 Baths

  3839 W Flournoy St, Chicago, IL 60624

  Beautiful two-unit Greystone investment property. The first-floor unit features 4 spacious bedrooms and 1 full bathroom. The second-floor unit offers 5 large bedrooms and 1 full bathroom. The basement is duplexed with the first floor and includes an additional 1 bedroom and 1 bathroom, providing extended living space. Both main units boast impressive 10-foot ceilings and were updated

  Orlando Morales RE/MAX Premier

  3839 W Flournoy St, Chicago, IL 60624
• 

  

  /9

  $1,700,000

  $25K PRICE DROP

  • 6 Beds
  • 7 Baths

  1623 N Halsted St, Chicago, IL 60614

  Located at 1623 N Halsted, this 3 unit, 5,388 SF property is ideally positioned in one of Chicago's most dynamic and upscale neighborhoods-offering exceptional potential for residential or boutique hotel development. The ground floor former restaurant space offers the opportunity for an owner/user to open up shop and use the residential unit income to cover their mortgage or an investor looking

  Daniel Hyman Millennium Properties RE, Inc.

  1623 N Halsted St, Chicago, IL 60614
• 

  

  /30

  $989,000

  • 6 Beds
  • 4 Baths

  5936 N Melvina Ave, Chicago, IL 60646

  Welcome to this rarely available Triplex in Norwood Park! Completely updated in recent years including all new plumbing, electrical, windows, central heat/AC, kitchens & baths, entire paint job and much more. 2025 updates include entire building tuckpointed, concrete walkway & back patio, new garage roof. Sump and flood control system in front for a piece of mind. The rear includes a huge 3 story

  Konstantinos Bakas Advantage Realty Group

  5936 N Melvina Ave, Chicago, IL 60646
• 

  

  /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
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  /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
• 

  

  /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
• 

  

  /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

  • 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

Showing Results 441 - 480, Page 12 of 18