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Homes for Sale in Chicago, IL with 5-Bedrooms

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  • /41

    $595,000

    • 5 Beds
    • 3 Baths

    2165 N Moody Ave, Chicago, IL 60639

    Rare Legal Brick 3-Flat! Features two identical 2BR/1BA units and a stunning 1BR/1BA garden unit (gut-rehabbed in 2022 w/ new kitchen, bath, & electric). Meticulously maintained by long-term owners. Major upgrades include new furnaces (2023) for garden/1st floors. The building features coin laundry and a 2-car garage. Tenants pay electric. Incredible opportunity to capture market-rate rents in a

    Miguel Lopez Redfin Corporation

    2165 N Moody Ave, Chicago, IL 60639
  • /53

    $4,295,000

    • 5 Beds
    • 7 Baths
    • 6,815 Sq Ft

    1434 N Dearborn St, Chicago, IL 60610

    On one of the Gold Coast's most enchanting tree-lined streets, this limestone residence blends historic grace with modern sophistication. Set on an extraordinary 25x149 lot, the home offers soaring ceilings, original millwork, and elegant architectural detail seamlessly paired with subtle, natural Scandinavian design, and amazing outdoor space. Flooded with natural light throughout, every space

    Carrie McCormick @properties Christie's International Real Estate

    1434 N Dearborn St, Chicago, IL 60610
  • /19

    $68,900

    • 5 Beds
    • 1 Bath
    • 1,100 Sq Ft

    328 W 106th Place, Chicago, IL 60628

    CALLING ALL INVESTORS/REHABBERS! HERE IS YOUR NEXT GREAT $$$ MAKING PROJECT! Large 2 story single family 5 Bedroom, 2 bath home in the middle of Chicago's Roseland Community. House is ready for rehab and to make lots of $$$ for you! Will sell fast, Schedule your showing today! Property is sold in "as-is" condition, Seller offers no repair credits or makes any repairs. No termite or survey

    Ryan Cherney Circle One Realty

    328 W 106th Place, Chicago, IL 60628
  • /19

    $339,000

    • 5 Beds
    • 3 Baths
    • 1,950 Sq Ft

    7409 S Eggleston Ave, Chicago, IL 60621

    This spacious brick residence offers the best of both worlds: the flexibility and income potential of a two unit building with the low tax burden of a single-family home. The main residence layout features a classic layout with hardwood floors a separate dining room and a comfortable family room ideal for everyday living and entertaining four well-sized bedrooms on the second level provide

    Spiro Georgelos Standard Properties Group LLC

    7409 S Eggleston Ave, Chicago, IL 60621
  • /44

    $629,000

    • 5 Beds
    • 3 Baths
    • 3,038 Sq Ft

    6020 N Landers Ave, Chicago, IL 60646

    Welcome to 6020 N. Landers in highly desirable and serene Edgebrook which sits on a 45x125 lot. This expanded 2 story home features a rare 5 bedrooms - 2 on the main floor and 3 on the 2nd level and 3 full baths - one on each floor. Large and bright living and dining rooms feature gleaming wood floors and stately wood burning fireplace (not used by sellers). Updated kitchen has Silestone

    Jan Kupiec Baird & Warner

    6020 N Landers Ave, Chicago, IL 60646
  • /64

    $3,199,000 Open Sat 10AM - 12PM

    • 6 Beds
    • 7 Baths
    • 5,539 Sq Ft

    3711 N Magnolia Ave, Chicago, IL 60613

    Located in the heart of the highly sought-after Southport Corridor neighborhood and within the coveted Blaine Elementary district. This historic and architecturally significant home with a front facade consisting of incredible granite and stone, offers a rare opportunity to own a piece of architectural history, with interiors meticulously recreated for modern luxury living. Original details

    Juliana Yeager @properties Christie's International Real Estate

    3711 N Magnolia Ave, Chicago, IL 60613
  • /47

    $395,000

    • 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
  • /40

    $449,999

    • 5 Beds
    • 3 Baths

    5037 W West End Ave, Chicago, IL 60644

    Carefully maintained and beautifully updated, this legal 2-unit property with a third living space in the finished basement is located in the thriving Austin community. The first-floor unit features two bedrooms and one bathroom, while the second-floor unit offers three bedrooms and one bathroom. The basement "in-law suite" includes two bedrooms and one bathroom, making it ideal for extended

    Jonathan Lopez Realty of America, LLC

    5037 W West End Ave, Chicago, IL 60644
  • /19

    $759,000

    • 10 Beds
    • 4 Baths

    6402 S Greenwood Ave, Chicago, IL 60637

    RARE WOODLAWN 3-FLAT Greystone with EXCEPTIONAL unit sizes & STABILIZED PREMIUM cash flow. Strategically located just steps from the Obama Presidential Center, slated for its grand opening in June 2026. This is a turn-key, high-performing asset in the heart of one of Chicago's most high-growth corridors. INVESTMENT HIGHLIGHTS: FULLY OCCUPIED: The building is now fully leased, featuring

    Brittany Ramsey Keller Williams ONEChicago

    6402 S Greenwood Ave, Chicago, IL 60637
  • /21

    $429,000

    • 6 Beds
    • 1 Bath

    6534 S Honore St, Chicago, IL 60636

    Magnificent renovated two-flat building now available through the Cook County land bank homebuyer program. This fully rehabbed, all-brick multi-unit checks all boxes! This professionally gut-rehabbed property has been renovated with architectural plans and approved Chicago building permits, making it a turnkey investment opportunity or an ideal option for owner-occupants. Each expansive unit

    Tatianna Barnett Keller Williams Preferred Rlty

    6534 S Honore St, Chicago, IL 60636
  • /5

    $569,900

    • 11 Beds
    • 5 Baths

    1239 S Avers Ave, Chicago, IL 60623

    Exceptional House Hack Opportunity in North Lawndale - 3 Unit Building | 11 Bedrooms | 5 Bathrooms Incredible opportunity to own a cash-flowing 3-unit property with 11 bedrooms and 5 bathrooms located at 1239 S Avers Ave in Chicago's rapidly developing North Lawndale neighborhood. This oversized multi-unit building offers the perfect setup for a house hacker looking to live in one unit while

    Melchor Domantay Second City Real Estate

    1239 S Avers Ave, Chicago, IL 60623
  • /40

    $2,950,000

    • 5 Beds
    • 4.5 Baths
    • 3,767 Sq Ft

    6 N Carpenter St Unit 5B, Chicago, IL 60607

    Style, Substance, & Location offered in this enormous light filled 1/2 floor residence. Stunning skyline views and 2 huge, covered terraces. Residence 5B is a thoughtfully upgraded home with private elevator entry, 5 large suites (3 ensuite baths and 2 with shared jack & jill bath), 2 distinct offices, large family room, separate library area, massive living/dining/kitchen great room all sharing

    Craig Faust @properties Christie's International Real Estate

    6 N Carpenter St Unit 5B, Chicago, IL 60607
  • /52

    $799,999

    • 6 Beds
    • 3 Baths

    3975 W Barry Ave, Chicago, IL 60618

    Exceptional investment opportunity! This is a legal 2 unit brick brownstone. We just obtained the Certificate of Zoning Compliance. Property Certified as 2 total dwelling units. Home offers strong potential for both investors and owner-occupants. The building features spacious units with a highly desirable layout. The first-floor unit offers 2 bedrooms and 1 bathroom, the second-floor unit

    Leticia Andrade Fulton Grace Realty

    3975 W Barry Ave, Chicago, IL 60618
  • /48

    $660,000

    • 6 Beds
    • 3 Baths

    5007 N Lawndale Ave, Chicago, IL 60625

    Solid brick two unit building with garden unit located in the heart of Albany Park, just steps from Eugene Park and conveniently close to public transportation, shopping, and dining. The owner currently occupies the first-floor unit, the second-floor unit soon to be leased, and the basement unit is occupied-providing immediate income potential and flexibility for both owner-occupants and

    Israel Dominguez Realty of America, LLC

    5007 N Lawndale Ave, Chicago, IL 60625
  • /37

    $499,900 Open Sat 11AM - 2PM

    • 6 Beds
    • 3 Baths

    6419 S Kenwood Ave, Chicago, IL 60637

    Rare opportunity to own a beautifully maintained, turn-key legal two-unit in the heart of East Woodlawn, one of Chicago's fastest-growing neighborhoods. Ideally located just blocks from the transformative future Obama Presidential Library, this property offers both long-term stability and exciting growth potential. The first-floor unit features 2 bedrooms and 1 full bath, offering flexibility for

    Catherine Pabatao Coldwell Banker Realty

    6419 S Kenwood Ave, Chicago, IL 60637
  • /24

    $490,000

    • 5 Beds
    • 3 Baths
    • 1,900 Sq Ft

    3141 N Odell Ave, Chicago, IL 60707

    Turnkey Tudor with Fireplace, Finished Basement, and 2 Car Garage Beautiful turnkey all brick English Tudor home with a 2 car garage that blends classic charm with thoughtful updates. Refinished original hardwood floors highlight the main level and lead into a beautiful kitchen with stainless steel appliances. This spacious home offers five bedrooms with two conveniently located on the main level

    Colleen Berg Berg Properties

    3141 N Odell Ave, Chicago, IL 60707
  • /35

    $2,495,000

    • 7 Beds
    • 6 Baths

    1705 W Leland Ave, Chicago, IL 60640

    An exceptional opportunity awaits in the vibrant Ravenswood neighborhood. This handsome, historic residence combines elegant style, modern comfort, and rare investment potential. The property features a stunning luxury owner's duplex-up plus three well-appointed rental apartments, offering both refined living and multiple income streams. The owner's duplex-up is a true showpiece, with expansive

    Keith Goad Berkshire Hathaway HomeServices Chicago

    1705 W Leland Ave, Chicago, IL 60640
  • /14

    $599,900

    • 9 Beds
    • 6 Baths

    3107 W Polk St, Chicago, IL 60612

    Welcome to 3107 W Polk Street, an exceptional three-flat located in the vibrant neighborhood of East Garfield Park, Chicago. This solid multi-unit property offers an outstanding investment opportunity with its classic architecture and prime location. Each of the three spacious units is designed to provide comfortable living with ample natural light and modern amenities. Situated in East Garfield

    Romeo Harper Compass

    3107 W Polk St, Chicago, IL 60612
  • /36

    $599,900

    • 5 Beds
    • 4 Baths

    6552 S Evans Ave, Chicago, IL 60637

    Welcome to this well-appointed two-unit building in the Woodlawn Pointe section of West Woodlawn. Minutes from the Obama Presidential Center, University of Chicago and Hyde Park's dining, shopping and entertainment scene! Offering thoughtfully designed layouts and quality finishes throughout making this property a strong opportunity for an owner-occupant or investor. The top unit features a

    Dione Craft @properties Christie's International Real Estate

    6552 S Evans Ave, Chicago, IL 60637
  • /19

    $399,900

    • 9 Beds
    • 3 Baths

    6640 S Union Ave, Chicago, IL 60621

    Welcome to this beautifully renovated GREYSTONE 2-unit property offering incredible income potential and future upside. This oversized building features a massive duplex-down first unit with 5 bedrooms and 2 bathrooms, along with a spacious 4 bedroom, 1 bathroom second-floor unit-ideal for maximizing rental income. The property has been thoughtfully updated with modern finishes throughout, making

    Jaskirat Vig Blue Door Dave Inc

    6640 S Union Ave, Chicago, IL 60621
  • /16

    $309,999

    • 6 Beds
    • 2 Baths
    • 1,152 Sq Ft

    7707 S Damen Ave, Chicago, IL 60620

    WELCOME TO THIS BEAUTIFUL BRICK RAISED RANCH. THIS HOME FEATURES A SPACIOUS MODERN LAYOUT WITH A TOTAL OF 6 BEDROOMS, 3 ON THE MAIN FLOOR AND 3 IN THE BASEMENT. THE PROPERTY BOASTS ELEGANT DECOR THROUGHOUT, INCLUDING GLEAMING HARDWOOD FLOORS AND UPDATED KITCHEN COMPLETE WITH CUSTOM CABINETRY, GRANITE COUNTERTOPS AND NEWER STAINLESS STEEL APPLIANCES. THE FINISHED BASEMENT OFFERS A LARGE

    Angelica Rodriguez Coldwell Banker Realty

    7707 S Damen Ave, Chicago, IL 60620
  • /11

    $294,900

    • 8 Beds
    • 3 Baths

    7514 S Dante Ave, Chicago, IL 60619

    INCOME INCOME INCOME Producing property!! Come see this great 2-Unit with 3 beds on the first floor and 3 beds on the 2nd floor to maximize your earning potential. The basement is finished as well, great for an in-law suite! The property is fully occupied so you can come in and start earning!! There has been many updates done to the property come an see for yourself. Schedule a showing today!

    George Sierra RE/MAX LOYALTY

    7514 S Dante Ave, Chicago, IL 60619
  • /85

    $1,595,000 Open House 4/12

    • 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
  • /24

    $599,000

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

    7241 N Mcvicker Ave, Chicago, IL 60646

    Welcome to 7241 McVicker, a fully rehabbed, move-in-ready ranch in Chicago. 3 Bedrooms on the main level and 2 additional bedrooms/multi-purpose rooms in the basement. beautiful chefs' kitchen and expansive yard. Too many highlights to list! Extremely motivated seller, schedule your showing today!

    Eliyahu Ben-Zev @properties Christie's International Real Estate

    7241 N Mcvicker Ave, Chicago, IL 60646
  • /42

    $875,000

    • 6 Beds
    • 5 Baths

    3816 W Montrose Ave, Chicago, IL 60618

    This 3-unit property is fully rented and a great income-producing investment opportunity or perfect for a Live/Work owner! Lots of recent updates: the roof was replaced 2 years ago, the front windows of the 2-bedroom were replaced in 2025, and both the 2-bed and the coach house have new electrical. The 1600 Sq. Ft. storefront is currently operating as a catering/restaurant business and is on a

    Lora Vasileva Cedar Realty

    3816 W Montrose Ave, Chicago, IL 60618
  • /28

    $849,000

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

    4545 N Lawndale Ave, Chicago, IL 60625

    Welcome home to this spacious open and airy 6 bedroom home in beautiful Albany Park close to Mayfair, Irving Park and Ravenswood. Features include vaulted high ceilings with skylights throughout, hardwood floors, fireplace, large gated yard, three full bedrooms on the second level with two more on the main floor and two separate finished basements including a possible in law suite. Enjoy the

    Kirby Pearson Pearson Realty Group

    4545 N Lawndale Ave, Chicago, IL 60625
  • /21

    $525,000

    • 13 Beds
    • 6 Baths

    5319 S Calumet Ave, Chicago, IL 60615

    Strategic Investment Opportunity: 4 individual furnace and water heater-Unit Value-Add Near Obama Center Unlock Immense Appreciation in a Growing Tech & Cultural Hub Position yourself at the forefront of Chicago's South Side revitalization with this high-yield 4-unit property. Perfectly situated "right up the street" from the landmark Obama Presidential Center, which is confirmed to open in June

    Marcus Maxwell Green Breeze Realty LLC

    5319 S Calumet Ave, Chicago, IL 60615
  • /32

    $408,000

    • 6 Beds
    • 2 Baths

    6331 S Justine St, Chicago, IL 60636

    Welcome to a beautifully remodeled 2unit building that feels inviting from the moment you step inside. Each spacious 3bedroom, 1bath unit offers a warm, comfortable layout with bright living spaces, generous bedrooms, and the kind of natural light that makes a home feel alive. This property is ideal for anyone dreaming of living in one unit while generating income from the other. It's also a

    Spiro Georgelos Standard Properties Group LLC

    6331 S Justine St, Chicago, IL 60636
  • /20

    $119,000

    • 8 Beds
    • 4 Baths

    11130 S Eggleston Ave, Chicago, IL 60628

    4- unit building for sale at a great price. THIS HOME IS OFFERED WITH A MOTIVATED SELLER. THIS IS NOT A BANK SHORT SALE OR FORECLOSURE. GREAT OPPORTUNITY FOR OWNERSHIP AT THIS PRICE. VACANT AND EASY TO SHOW. PLEASE INSPECT PRIOR TO SUBMITTING AN OFFER SINCE WE ARE SELLING "AS-IS". NO SURVEY. DISCLOSURES UNDER ADDITIONAL DOCUMENTS. AGENT HAS AN OWNERSHIP INTEREST IN THE PROPERTY.

    Timothy Gray The Chicagoland RE Auction Co.

    11130 S Eggleston Ave, Chicago, IL 60628
  • /64

    $450,000

    • 5 Beds
    • 3 Baths
    • 2,970 Sq Ft

    8631 S Constance Ave, Chicago, IL 60617

    All Brick & Stone Home, very rare and unique find style home. unique Roof Deck, Home has total of 5 huge Bedrooms, 3 full bathrooms & 2 Stone Fireplaces. Total home Sq. Ft. is 1980 and 2970 including 2 Master bedrooms (1st level and 2nd Level). Finished Basement. New Huge Deck off the kitchen, New Fenced backyard with mature trees, 2 detached car garage. Home is totally updated and remodeled, New

    Ryed Douedari Coldwell Banker Realty

    8631 S Constance Ave, Chicago, IL 60617
  • /17

    $549,900

    • 5 Beds
    • 3 Baths

    2045 N Tripp Ave, Chicago, IL 60639

    Great opportunity to own a zoned 2-flat in the highly sought-after Hermosa neighborhood of Chicago. Each unit features a spacious layout with separate living and dining rooms, two generously sized bedrooms, a full bathroom, and an eat-in kitchen with pantry space. Hardwood floors run throughout the living rooms, dining rooms, and bedrooms, adding warmth and character to both units. The finished

    Giuseppe Zerillo Zerillo Realty Inc.

    2045 N Tripp Ave, Chicago, IL 60639
  • /35

    $629,900

    • 6 Beds
    • 6 Baths

    6350 S Champlain Ave, Chicago, IL 60637

    Welcome Home! Take this opportunity to own a fully rehabbed Chicago Greystone. This legal 2-unit property feels like 3 units. Property includes an in-law arrangement in the lower level with separate entry. Great opportunity for generational living or short-term rental. Build equity while living in one unit and benefit from rental income to assist with mortgage payments. This property features a 3

    LaVette Jones ARNI Realty Incorporated

    6350 S Champlain Ave, Chicago, IL 60637
  • /18

    $420,000

    • 6 Beds
    • 2 Baths

    4505 S Justine St, Chicago, IL 60609

    All-brick, recently-remodeled 2-flat located off Ashland Ave. Both units have 3 bed/1 bath, and are gorgeously renovated, with a deck overlooking the backyard. The units feature a generously-sized living room, a formal dining area, & a newer contemporary kitchen complete with European-style cabinets, full glass tile backsplash, quartz countertops, & newer appliances. The bathroom boasts

    Virginia Gonzalez Village Realty, Inc.

    4505 S Justine St, Chicago, IL 60609
  • /37

    $795,000

    • 6 Beds
    • 4 Baths
    • 3,657 Sq Ft

    2416 W Morse Ave, Chicago, IL 60645

    Quintessential Chicago bungalow in the Tallman / West Ridge Bungalow Belt, ideally positioned between two of the neighborhood's most beloved green spaces-Indian Boundary Park and Warren Park. This fully reimagined six-window-wide brick bungalow blends timeless Chicago character with thoughtful modern design and remarkable flexibility for today's lifestyle. At the center of the home, the

    Trupti Patel Compass

    2416 W Morse Ave, Chicago, IL 60645
  • /45

    $1,400,000

    • 11 Beds
    • 7 Baths

    2900 W Glenlake Ave, Chicago, IL 60659

    Fully tenant-occupied, renovated 4-flat in sought-after West Rogers Park - an investor's dream opportunity. This turnkey building features a desirable unit mix: one 4-bedroom/2-bath, one 3-bedroom/2-bath, one 2-bedroom, 2 bath, and one 2-bedroom/1-bath unit. All residences have been updated with modern kitchens showcasing quartz countertops, stainless steel appliances, and crisp white cabinetry.

    Jacqueline Alter Redfin Corporation

    2900 W Glenlake Ave, Chicago, IL 60659
  • /26

    $295,000

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

    5541 W Grace St, Chicago, IL 60641

    Portage Park Handyman Special! This charming 5 bed 2 bath 2 kitchen home sits on a quiet tree lined street in Portage Park. The 1st floor features 3 bedrooms, spacious living room, formal dining room, updated bathroom, galley kitchen, and enclosed back porch. Basement features 2 more bedrooms, 2nd kitchen, 2nd bathroom, family room, and laundry area. The attic is accessible but unfinished. There

    gershon draiman Pearson Realty Group

    5541 W Grace St, Chicago, IL 60641
  • /16

    $484,000

    • 5 Beds
    • 2 Baths

    3510 N Oketo Ave, Chicago, IL 60634

    Modern Elegance Meets Every-Day Comfort - step into a home where every detail has been meticulously curated for the modern lifestyle. This beautifully updated two-story residence welcomes you with an expansive, sun-drenched open floor plan and gleaming new floors that flow seamlessly from room to room. At the heart of the home, the designer kitchen shines with crisp white shaker cabinetry, sleek

    Peter Deja Cross County Realty Inc.

    3510 N Oketo Ave, Chicago, IL 60634
  • /37

    $334,900

    • 7 Beds
    • 4 Baths

    5114 S Justine St, Chicago, IL 60609

    A LEGAL 2-UNIT with a FINISHED BASEMENT and FINISHED ATTIC, offering TONS OF POTENTIAL for owner-occupants or investors. Both units feature 3 BEDROOMS, making this a GREAT AREA FOR RENTAL OPPORTUNITY with strong demand. The property includes a ROOF APPROX. 10 YEARS OLD, UPDATED ELECTRICAL, and COPPER PLUMBING for peace of mind. Conveniently located near MAJOR HIGHWAYS, including the I-55

    Xochil Wendy Escobar Realty of America, LLC

    5114 S Justine St, Chicago, IL 60609
  • /19

    $525,000

    • 11 Beds
    • 7 Baths

    7637 S Phillips Ave, Chicago, IL 60649

    This beautiful and spacious legal 3 unit with a garden. Features three oversized (3)3-bedroom two full bathrooms and two bedroom one bathroom garden unit. Individual heat and a/c for each unit. Complete with a brick 3 car garage, this property is ideal for both investors and owner-occupants....Some work done to units. Don't miss this opportunity!!!!!!!!!!!!!! Sold AS-IS

    Monique Rhivers Blue Door Dave Inc

    7637 S Phillips Ave, Chicago, IL 60649
  • /22

    $498,000

    • 6 Beds
    • 2 Baths
    • 2,280 Sq Ft

    1835 W 34th St, Chicago, IL 60608

    Beautiful Brick Single-Family Home in the rapidly growing McKinley Park neighborhood! This spacious residence offers 6 bedrooms and 2 full baths with a functional layout and modern updates. The main floor features 3 bedrooms, 1 bath, and a bright kitchen with custom cabinets, granite countertops, and stainless steel appliances including refrigerator, stove, dishwasher, microwave, and exhaust fan.

    Michael Ng Mango Realty Group

    1835 W 34th St, Chicago, IL 60608

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