5-Bedroom Homes for Sale in Chicago, IL

• 

  

  

  /19

  $299,900 Open Sun 1PM - 2PM

  • 6 Beds
  • 3 Baths

  1704 S Racine Ave, Chicago, IL 60608

  Great Opportunity To Build New or Own 2 Flat In Ideal Pilsen Location With Downtown Views. Property is offered for sale as "LAND" (Teardown) or "AS iS" 2 Flat. Owner will sell property with plans developed for a New Construction 3 Unit with jumbo three bedroom Units custom designed for site. Second option: rehab building and keep it. If you want to keep what's there it is the Perfect

  Phil Buoscio Keller Williams ONEChicago

  1704 S Racine Ave, Chicago, IL 60608
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  /36

  $795,000

  • 10 Beds
  • 5 Baths

  7062 W Diversey Ave, Chicago, IL 60707

  Refurbished LEGAL three-flat offering exceptional cash flow and long-term equity potential. Units boasts spacious floor plans with oversized bedrooms and wide layouts. The top floor and middle unit are about 1,417 sq. ft. while lower level unit is about 1,000 sq ft. The 1st and 2nd floor units feature 4 bedrooms and 2 full baths-designed to capture premium rents in this rental market. Nearby

  Karla Mina MPower Residential Brokerage LLC

  7062 W Diversey Ave, Chicago, IL 60707
• 

  

  

  /23

  $599,000

  • 5 Beds
  • 2 Baths

  947 W 18th St, Chicago, IL 60608

  Nicely updated 2-flat in prime East Pilsen! Freshly remodeled first-floor owner's unit with new kitchen, bath, and flooring. The property offers two spacious units: a 2BD/1BA on the first floor (vacant, est. rent $2,400/month) and a 3BD/1BA on the second floor ( at $2,200/month). Recent updates within the last year include new siding, gutters, windows, water heater, parking pad, and fence. New

  Tamara Verdin Prello Realty

  947 W 18th St, Chicago, IL 60608
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  /5

  $210,000

  • 5 Beds
  • 2 Baths

  6815 S Green St, Chicago, IL 60621

  Investor Special! Well-maintained 2-Flat in growing Englewood with strong income potential. Estimated rents support a healthy CAP rate. Second-floor unit features a unique duplexed layout, creating a spacious 3BR with extra living space. Unfinished basement offers value-add potential for storage or additional units (pending permits). Secure off-street parking with cast iron gates. Turnkey

  Claes Brameus Coldwell Banker Realty

  6815 S Green St, Chicago, IL 60621
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  /76

  $769,900

  • 7 Beds
  • 5 Baths

  1800 S Jefferson St, Chicago, IL 60616

  INVESTORS !!! There is a front corner commercial space not counted in the 4 Unit building 400SQ/FT. LOCATION, LOCATION , LOCATION - Welcome! This urban newer renovated 4-Multi Unit Apartment Bldg. along with 1 commercial Kitchen store front. Is located on the corner of Jefferson and 18th Sreet. In vibrant East Pilsen one of Chicago's most dynamic neighborhoods. Experience this exceptional

  Ciso Contreras Realty of America, LLC

  1800 S Jefferson St, Chicago, IL 60616
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  /13

  $499,000

  • 6 Beds
  • 4 Baths

  3838 W Gladys Ave, Chicago, IL 60624

  Opportunity awaits with this classic Greystone 4-unit building on Chicago's West Side. Just steps from a beautiful park, near public transportation, and minutes from the I-290 expressway for a quick commute downtown, this property is ideally located in a community on a strong upswing. The building was rehabbed several years ago with updated kitchens, baths, electrical, and separate heating

  La Shawn K Ford Ford Desired Real Estate LLC

  3838 W Gladys Ave, Chicago, IL 60624
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  /18

  $300,000

  • 5 Beds
  • 2 Baths

  4730 W Arthington St, Chicago, IL 60644

  Attention investors. Multi unit opportunity at 4730-32 W Arthington. Property also comes with a Coach House. This property boasts a sizeable lot 75X126 which will offer you the potential to expand the existing footprint or consider future development possibilities. This property will require extensive work. The two unit building, the two garages and the coach house are being sold "AS IS".

  Evelyn Humphries Berkshire Hathaway HomeServices Chicago

  4730 W Arthington St, Chicago, IL 60644
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  /49

  $575,000

  • 6 Beds
  • 3 Baths

  2016 N Kilbourn Ave, Chicago, IL 60639

  Pride of Ownership! Check out this updated and versatile brick two-flat in vibrant Hermosa neighborhood. The first-floor unit is duplexed to the finished basement, offering 4 bedrooms, 2 baths, a family room, an interior spiral staircase, Dining room with sliding doors to the side and large rear deck. Also, lower level features a separate front entrance with its own GFA heating system. The

  Dalia Cajigas Re/Max Cityview

  2016 N Kilbourn Ave, Chicago, IL 60639
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  /9

  $119,900

  • 7 Beds
  • 3 Baths

  7137 S Carpenter St, Chicago, IL 60621

  GREYSTONE TWO UNIT ready for rehab. Two bedroom apartment previously in the basement. First floor 2 bedroom and second floor 3 bedroom. Property in need a lot of work, but will be a good investment/flip. Sold as is. No survey provided.

  David Williamson Choice Realty Group Inc.

  7137 S Carpenter St, Chicago, IL 60621
• 

  

  /22

  $499,900

  • 7 Beds
  • 3 Baths

  6004 S Kolmar Ave, Chicago, IL 60629

  Rarely available 2 flat, on an over sized city lot! 30x198 deep. This home was used as a single family home by the original owners for over 50 years. It is a legal 2 flat. Unit 1 is a duplex down with 5 beds, 2 full baths, living room, and huge family room, with bar. Newer front windows. Updated Kitchen features granite counters, plenty of cabinet and counter space, along with separate area for a

  Timothy Sullivan Baird & Warner

  6004 S Kolmar Ave, Chicago, IL 60629
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  /20

  $399,900

  • 6 Beds
  • 2 Baths

  7912 S Ada St, Chicago, IL 60620

  Welcome home to this beautifully upgraded brick two-flat nestled in the heart of Auburn Gresham. Offering close to 1,300 sq. ft. of living space per unit, this property is ideal for investors or owner-occupants looking to generate rental income. Each spacious unit features 3 bedrooms, 1 full bathroom, a generous living room, and a traditional separate dining room, perfect for everyday living and

  Anna Comer HomeSmart Realty Group

  7912 S Ada St, Chicago, IL 60620
• 

  

  /22

  $490,000

  • 5 Beds
  • 2 Baths

  3736 W Cermak Rd, Chicago, IL 60623

  Stunning Greystone 2-Flat - A Turnkey Investor's Dream, where timeless charm meets modern luxury! All major work completed ensuring a hassle-free investment. Offering two spacious units. The first floor presents a unique opportunity to duplex down into the basement, which can create additional living or entertainment space. The second-floor unit features a third bedroom, maximizing rental

  Rachel Ruffin Executive Realty Group LLC

  3736 W Cermak Rd, Chicago, IL 60623
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  /8

  $215,000

  • 6 Beds
  • 2 Baths

  31 W 112th Place, Chicago, IL 60628

  Amazing investment opportunity! Framed 2 flat offering main floor current mo to mo tenant at 1200/mo. 2nd floor 3 bed 1 bath ready for its next tenant. Each unit has separate electric, HWH, and heat. Full unfinished basement has bath and shower rough-in. Enjoy current cash flow or make it your own investment.

  Mark Rantis Keller Williams Success Realty

  31 W 112th Place, Chicago, IL 60628
• 

  

  /20

  $365,000

  • 5 Beds
  • 3 Baths

  940 N Leclaire Ave, Chicago, IL 60651

  Investor's Dream or Perfect House Hack Opportunity! Welcome to 940 N Leclaire, a solid brick building located in the heart of Chicago's Austin neighborhood. This property offers 2 legal units plus a fully finished basement, all currently occupied by reliable, on-time month-to-month tenants-a great source of immediate rental income. Whether you're an investor looking to expand your portfolio or a

  Patricio Tacuri Internet Real Estate, LTD.

  940 N Leclaire Ave, Chicago, IL 60651
• 

  

  /23

  $299,999

  • 6 Beds
  • 3 Baths

  5721 S Hermitage Ave, Chicago, IL 60636

  Say hello to this income generating machine!! This beautiful Chicago 2 flat building is ready for a new owner! First floor unit is duplexed into your finished basement that offers FOUR bedrooms and TWO full bathrooms, upstairs unit offers two spacious bedrooms and a full bathroom. Each unit has beautiful floors throughout, sought after high ceilings and gorgeous quartz countertops in the

  Cesar Garcia Avenue Properties Chicago

  5721 S Hermitage Ave, Chicago, IL 60636
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  /10

  $270,000

  • 6 Beds
  • 5 Baths

  6911 S Jeffery Blvd, Chicago, IL 60649

  Solid Brick 2-Flat with great potential! Each spacious unit offers 3 bedrooms and 2 full bathrooms, providing plenty of room for comfortable living. The property also features a full basement with an additional bathroom, offering extra living or storage options. A 2-car brick detached garage adds value and convenience. While the property needs some TLC, it has good bones and is a fantastic

  Kason Wallace Premier Midwest Realty, INC

  6911 S Jeffery Blvd, Chicago, IL 60649
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  /49

  $295,000

  • 5 Beds
  • 3 Baths

  8210 S Manistee Ave, Chicago, IL 60617

  Nestled on a generous 48' x 124' lot, this versatile 2-family property offers an exceptional opportunity for homeowners and investors alike. With a spacious layout, classic features, and modern conveniences, this property is a must-see! Brand new siding throughout. Unit 1: This expansive unit is duplexed to the basement, offering 4 bedrooms and 2 bathrooms. The main level boasts beautiful

  Crystal Smith, REALTOR® Illinois Real Estate Partners

  8210 S Manistee Ave, Chicago, IL 60617
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  /50

  $1,899,000

  • 6 Beds
  • 3 Baths

  2026 N Humboldt Blvd, Chicago, IL 60647

  Welcome to this amazing red brick 2 flat on historic Humboldt Blvd. This well preserved and maintained classic beauty sits on a double Chicago lot with a Unilock paved brick side driveway and patio. The 2 unit building features the best of both worlds, classic beautiful wood work, hardwood flooring, crown molding and modern amenities like remodeled kitchens and baths. Both units offer 7 large

  Colette Cook arhome realty

  2026 N Humboldt Blvd, Chicago, IL 60647
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  /45

  $784,900

  • 6 Beds
  • 5 Baths

  8423 W Wilson Ave, Chicago, IL 60656

  Impressive 6 bed, 5 bath home in the desirable Forest View subdivision, perfectly located near Schiller Woods and the Kennedy Expressway (I-90). Steps from bike paths, parks, shopping, dining, Mariano's, Harlem Irving Plaza, fitness studios and more! Only a 7-minute drive to Fashion Outlets of Chicago, Rosemont Theatre, and Parkway Bank Entertainment District. The 1st and 2nd floor each feature a

  Eva Sachman Turek Berkshire Hathaway HomeServices Chicago

  8423 W Wilson Ave, Chicago, IL 60656
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  /27

  $219,999

  • 5 Beds
  • 3 Baths

  4329 S Wood St, Chicago, IL 60609

  ***** CASH OR REHAB LOANS ONLY ***** Rarely available fully Remodeled Legal 3 unit!! Buillding consists of a total of 5 bedrooms and 3 bathrooms. On the first floor unit you will encounter an open concept kitchen/living room area along with 2 bedrooms, huge pantry, and 1 full bath.On the second level unit, you find another 2 bedrooms, 1 bath, with a full kitchen and living room. Downstairs in the

  Jonathan Lopez Realty of America, LLC

  4329 S Wood St, Chicago, IL 60609
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  /30

  $699,900

  • 6 Beds
  • 3 Baths

  5233 W Parker Ave, Chicago, IL 60639

  Welcome to 5233 W Parker, a beautifully maintained brick two-flat in the heart of Belmont Cragin. Both units are identical and feature spacious living rooms with bay windows that flood the space with natural light, separate dining rooms perfect for entertaining, three generous bedrooms with ample closet space, and bright kitchens with a cozy sitting area overlooking the yard, all enhanced by

  Leslie Roman Realty of America, LLC

  5233 W Parker Ave, Chicago, IL 60639
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  /37

  $1,035,000

  • 9 Beds
  • 6 Baths

  4634 S Langley Ave, Chicago, IL 60653

  Attention Investors and Owner-Occupants! Don't miss this stunning new construction 3-unit building in the heart of Bronzeville. Each unit features 3 bedrooms, 2 baths, a spacious living room, and a custom-designed kitchen with appliances, ample cabinet space, a wine rack, garbage pull-out, and granite countertops. Enjoy premium finishes like hardwood floors, ceramic tile, and carpet, plus modern

  Omor Eguasa Baird & Warner

  4634 S Langley Ave, Chicago, IL 60653
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  /55

  $1,199,900

  • 8 Beds
  • 4 Baths

  2512 N Marshfield Ave, Chicago, IL 60614

  Fantastic, fully leased 3-Flat tucked away on charming Marshfield Street in the heart of Lincoln Park. A complete curb appeal upgrade with a fully rebuilt front porch, metal fence, new gate, all new concrete retaining wall and refreshed exterior lighting + landscaping. This turn-key property features three thoughtfully updated units generating strong rental income with room for growth and low

  Elizabeth Lothamer Compass

  2512 N Marshfield Ave, Chicago, IL 60614
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  /60

  $745,000

  • 8 Beds
  • 3 Baths

  6347 S Drexel Ave, Chicago, IL 60637

  $15,000 seller credit and a low interest rate! A Greystone rebuilt with permits in vibrant Woodlawn. This 2023 gut-rehab blends historic elegance with modern upgrades. Potential rental income of up to $6,000/month. With the seller's credits you can reduce your mortgage payment to around $4,000, offering up to a potential $2,000 in monthly profit. The property features tall ceilings, hardwood

  Phillip Dixon Compass

  6347 S Drexel Ave, Chicago, IL 60637
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  /61

  $4,195,000

  • 5 Beds
  • 5 Baths
  • 7,600 Sq Ft

  2107 N Dayton St, Chicago, IL 60614

  As featured in Crain's, this AIA award-winning Modernist home is both an architectural and technological feat. Spanning a double lot, the residence is discreetly set behind an understated facade that blends seamlessly into the streetscape. Inside, the warm modern design reveals extraordinary volume, abundant natural light, exceptional privacy, and a rare connection to the outdoors. Distinctive

  Jennifer Ames Engel & Voelkers Chicago

  2107 N Dayton St, Chicago, IL 60614
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  /50

  $400,000

  • 5 Beds
  • 3 Baths

  6241 S Troy St, Chicago, IL 60629

  Beautiful Multi-Unit Opportunity! This well-maintained property offers excellent investment potential. The first unit features two generously sized bedrooms with a large living room and separate dining room with a brand new kitchen and bath. While the second unit includes three comfortable bedrooms a large living room and new bathroom. Both floors include a back bonus room for an office or

  Diana Nufio Realty of America, LLC

  6241 S Troy St, Chicago, IL 60629
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  /29

  $499,999

  • 5 Beds
  • 3 Baths
  • 990 Sq Ft

  5505 W Parker Ave, Chicago, IL 60639

  Experience modern luxury in this beautifully updated 6-bedroom, 3-bath single-family home located in the heart of Belmont Cragin. The gourmet kitchen is a true centerpiece, boasting quartz waterfall countertops, custom cabinetry, premium stainless steel appliances, and a designer backsplash. Each level offers 2 spacious bedrooms and a full bath, while the finished attic and basement provide

  Edison N Orejuela Realty of America, LLC

  5505 W Parker Ave, Chicago, IL 60639
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  /27

  $799,900

  • 8 Beds
  • 5 Baths

  8449 W Brodman Ave, Chicago, IL 60656

  BEAUTIFUL SPACIOUS 2 FLAT IN NORWOOD PARK. THIS BUILDING IS LOCATED IN CHICAGO BUT IS VERY CLOSE TO NORRIDGE. GREAT LOCATION, CLOSE TO PARKS, SHOPPING AND TRANSPORTAION. THIS ALL BRICK BUILDING IS LOCATED ON A QUIET CUL-DE-SAC STREET WITH VERY LITTLE TRAFFIC. THE FIRST AND SECOND FLOOR LAYOUTS FEATURE A LARGE LVING ROOM AND DINING COMBINATION, 3 BEDROOMS, EACH UNIT HAS A MASTER SUITES WITH FULL A

  Michael Lohens RE/MAX Properties Northwest

  8449 W Brodman Ave, Chicago, IL 60656
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  /25

  $559,000

  • 7 Beds
  • 3 Baths

  6336 S Eberhart Ave, Chicago, IL 60637

  GREAT WOODLAWN INVESTMENT OPPORTUNITY, NEW CONTRUCTION ALL AROUND, INCLUDES A NEW MULTI MILLION DOLLAR COMMUNITY CENTER JUST FOOTSTEPS AWAY. OBAMA LIBRARY NEARBY. Welcome to 6336 S Eberhart, a stunning newly rehabbed two-unit property that has been thoughtfully renovated from top to bottom. The spacious lower unit is duplexed into the basement, offering a generous layout with 4 bedrooms and 2

  Johnathan Clancy Keller Williams Premiere Properties

  6336 S Eberhart Ave, Chicago, IL 60637
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  /35

  $269,900

  • 8 Beds
  • 3 Baths

  7836 S Constance Ave, Chicago, IL 60649

  *Multiple Offers Received. Highest and Best due by 9-11-25.* Gain instant sweat-equity with this classic brick 3-unit in the Auburn Gresham. This property offers two 3-bed, 1-bath units featuring and one 2-bed, 1-bath: sun-filled living rooms with decorative fireplaces; formal dining rooms; large kitchens with shaker cabinets, quartz counts, stainless appliances and loads of storage; stylish

  Anthony Disano Parkvue Realty Corporation

  7836 S Constance Ave, Chicago, IL 60649
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  /44

  $2,650,000 Open Sat 12PM - 1:30PM

  • 5 Beds
  • 4.5 Baths
  • 4,600 Sq Ft

  3509 N Janssen Ave, Chicago, IL 60657

  Situated on one of the most desirable blocks in the Southport Corridor, 3509 N Janssen is a sophisticated residence that combines timeless design with exceptional craftsmanship. Flooded with natural light, this five-bedroom, four-and-a-half-bath home showcases custom millwork, rich detailing, and premium finishes throughout. At its center is a thoughtfully designed chef's kitchen, anchored by a

  Matt Leutheuser Jameson Sotheby's Intl Realty

  3509 N Janssen Ave, Chicago, IL 60657
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  /16

  $1,149,999

  • 7 Beds
  • 3 Baths

  2014 N Whipple St, Chicago, IL 60647

  Prime multi-unit investment opportunity offering both immediate cash flow and long-term stability. This well-maintained property is fully rented, including several long-term tenants, providing consistent income from day one. The first-floor unit has been recently renovated with modern finishes, while the upper levels remain occupied and performing. Located in the highly sought-after Logan Square

  Daniel Walus OnPath Realty Inc.

  2014 N Whipple St, Chicago, IL 60647
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  /69

  $5,995,000

  • 6 Beds
  • 11 Baths
  • 9,000 Sq Ft

  950 N Michigan Ave Unit 4605, Chicago, IL 60611

  Perched near the top of one of Chicago's most iconic addresses, Unit 4605 at One Magnificent Mile is a rare, architecturally significant duplex offering nearly 9,000 square feet of masterfully curated living space. Designed by Wheeler Kearns Architects with interiors by Set Setting Studio, this 6 bedroom, 8 full and 3 half bathroom residence combines warm contemporary design with sweeping views

  Ryan Preuett Jameson Sotheby's Intl Realty

  950 N Michigan Ave Unit 4605, Chicago, IL 60611
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  /25

  $249,900

  • 5 Beds
  • 2 Baths
  • 3,554 Sq Ft

  10001 S Wentworth Ave, Chicago, IL 60628

  Welcome to this spacious and recently renovated 5 bedroom 2 bathroom single-family home. Step inside to discover beautiful hardwood floors and spacious floorplan, perfect for accommodating a growing family or hosting gatherings. The kitchen boasts white shaker cabinets, quartz countertops , stainless steel appliances and an open-concept design. The full basement provides additional storage

  Mary Derman Keller Williams Preferred Rlty

  10001 S Wentworth Ave, Chicago, IL 60628
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  /32

  $455,000

  • 7 Beds
  • 3 Baths

  4336 W Adams St, Chicago, IL 60624

  Gorgeous Greystone in Hot West Garfield! This unique 2 flat has just been rehabbed and boasts 7 bedrooms and 3 baths! The first floor has been duplexed to the basement with 2 bedrooms and a bath on each floor. Perfect for an owner's unit. Perfect investment for owner occupied, cash flow play, or related living! ! Too many upgrades to mention. Come check it out before it's gone!

  Ryan Cherney Circle One Realty

  4336 W Adams St, Chicago, IL 60624
• 

  

  /22

  $175,000

  • 5 Beds
  • 2 Baths
  • 1,470 Sq Ft

  256 W 112th Place, Chicago, IL 60628

  Discover this freshly renovated (2025) 5-bedroom, 2-bathroom single-family home on a spacious corner lot in Chicago's South Side. This property is perfect for families looking for more space or investors seeking a strong rental opportunity. Inside, you'll find new carpet, luxury vinyl flooring, and fresh paint throughout. The modern kitchen features newer appliances, quartz countertops, and

  Luis Ortiz Shield Real Estate

  256 W 112th Place, Chicago, IL 60628
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  /12

  $600,000 Open Sat 12PM - 2PM

  • 9 Beds
  • 6 Baths

  6807 S Paulina St, Chicago, IL 60636

  This newly renovated 3-unit brick building is the perfect opportunity for both investors and owner-occupants. Each spacious unit offers 3 bedrooms and 2 full bathrooms, along with beautifully updated kitchens featuring butcher block countertops, farmhouse sinks, and stainless steel appliances. Washer and dryer hookups add convenience to each home. The property also features a low-maintenance

  Lonzetta McKennie @properties Christie's International Real Estate

  6807 S Paulina St, Chicago, IL 60636
• 

  

  /31

  $529,000

  • 9 Beds
  • 3 Baths

  4938 W Rice St, Chicago, IL 60651

  Perfectly located on quiet tree lined street in the heart of Austin and meticulously updated throughout on a oversized 30' x 125' lot with new electricals, plumbing, and HVAC. Completely renovated 2 legal units with fully finished garden unit with separate utilities. The living room boast oversized windows with abundance of natural light. Highly upgraded kitchen with microwave, dishwasher,

  Brian Waters Mentor Listing Realty Inc.

  4938 W Rice St, Chicago, IL 60651
• 

  

  /26

  $750,000

  • 7 Beds
  • 3 Baths

  5814 N Campbell Ave, Chicago, IL 60659

  This updated and well maintained 2-Flat with garden apartment is situated on an extra-wide lot along a picturesque, tree-lined street in the desirable Arcadia Terrace Neighborhood. The building's wider footprint allows for spacious room sizes throughout. The first-floor kitchen is brand new, featuring high-end finishes and an open layout that connects seamlessly to the dining room, creating a

  Michael Hall Baird & Warner

  5814 N Campbell Ave, Chicago, IL 60659
• 

  

  /35

  $570,000

  • 5 Beds
  • 3 Baths

  5532 S Kilbourn Ave, Chicago, IL 60629

  Completely remodeled and updated property with stainless steel appliances, new cabinets and countertops, new Brazilian Cherry hardwood floors all around, new glass handrails, new bathrooms, etc. Everything is new including the entire electrical system, new copper water lines everywhere, new gas lines, etc. Must see property that can easily be rented or used for AirBNB because it is within

  Ryan Cherney Circle One Realty

  5532 S Kilbourn Ave, Chicago, IL 60629

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