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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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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