5-Bedroom Homes for Sale in Chicago, IL

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  /50

  $699,000

  • 5 Beds
  • 4 Baths
  • 3,800 Sq Ft

  232 E Walton Place Unit 3W, Chicago, IL 60611

  Historic Elegance Meets Modern Possibility in the Heart of Streeterville Welcome to 232 E Walton Place - an architectural gem nestled on a tree-lined street in one of Chicago's most iconic neighborhoods. Situated just steps from Lake Michigan, Oak Street Beach, and the Magnificent Mile, this distinguished half-floor residence offers 3,800 square feet of timeless elegance and endless potential in

  Lauren Schuh-Dayton Jameson Sotheby's Intl Realty

  232 E Walton Place Unit 3W, Chicago, IL 60611
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  /38

  $525,000

  • 5 Beds
  • 3 Baths

  4229 N Kedzie Ave, Chicago, IL 60618

  Welcome to Albany Park! This charming 2-flat property is perfect for owner-occupants looking to generate rental income. The top unit features a spacious duplex-up layout with 3 bedrooms & 1.1 bathrooms. Top unit also offers updated kitchen cabinetry. The first-floor unit offers 2 bedrooms and 1 bathroom. Both units boast updated bathrooms, modern light fixtures, and beautifully refinished floors

  Adam Zagata Baird & Warner

  4229 N Kedzie Ave, Chicago, IL 60618
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  /26

  $655,000

  • 9 Beds
  • 6 Baths

  5905 S Indiana Ave, Chicago, IL 60637

  Incredible Investment Opportunity - Fully Updated 3-Flat with Immediate Cash Flow Potential! Welcome to this exceptional brick 3-flat, a rare find offering both modern updates and strong rental income potential. Two of the three spacious units are already leased to long-term tenants, making this a turnkey investment for the savvy buyer-or an owner-occupant looking to live in one unit while

  Randi Quigley eXp Realty

  5905 S Indiana Ave, Chicago, IL 60637
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  /10

  $220,000

  • 5 Beds
  • 2 Baths

  8533 S Muskegon Ave, Chicago, IL 60617

  Solid 2 unit building with good structure, live in one and rent the other. Possibility to convert second floor unit to duplex. Newer copper/PVC plumbing, and upgraded gas meters. Reliable and quiet tenant upstairs. Dry basement with ample space for storage. No garage but plenty of space for parking in back.

  Tony Salas Baird & Warner

  8533 S Muskegon Ave, Chicago, IL 60617
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  /21

  $389,900

  • 6 Beds
  • 2 Baths

  223 W 118th St, Chicago, IL 60628

  Updated Two-Unit Building with Separate Mechanical Systems and Gated Parking! This fully updated two-unit property is move-in ready and ideal for both investors and owner-occupants. Recent improvements include a new roof, new plumbing, new electrical, new bathrooms, new flooring, and updated bedrooms in both units. Kitchens are upgraded with marble countertops and modern finishes. Each unit

  Doris E Rivera Coldwell Banker Realty

  223 W 118th St, Chicago, IL 60628
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  /16

  $479,900

  • 8 Beds
  • 2 Baths

  2341 N Major Ave, Chicago, IL 60639

  !! Spacious 2 Flat in Belmont-Cragin Area !! Lower unit has 3-bedrooms, 1-bath and Upper Unit has 5-bedrooms, 2-baths. Upgrades include New Siding & Roof in 2025, Updated Windows, Updated Furnance Units and Circuit Breakers. Conveniently located to train stations, walking distance to schools and parks. Potential to generate $3,000 monthly rental income. Perfect for Large Families and

  Martin Maliekal Kenneth Mason Realty

  2341 N Major Ave, Chicago, IL 60639
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  /35

  $224,900

  • 5 Beds
  • 2 Baths

  1019 N Leamington Ave, Chicago, IL 60651

  Located in heart of the Austin community which happens to be one of the most sought after communities in Chicago this is a solid all brick multi unit that you can not overlook! The building features all the charm and character you would come to expect from a multi unit with hardwood floors throughout, original wood trim, formal dining rooms in each unit and overall very spacious layouts. The main

  Ryan Smith RE/MAX Premier

  1019 N Leamington Ave, Chicago, IL 60651
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  /3

  $450,000

  • 5 Beds
  • 3 Baths

  2214 N Mango Ave, Chicago, IL 60639

  Beautifully updated 2-unit home in Belmont Cragin! The main unit features 4 bedrooms and 2 bathrooms, a bright and spacious living room, modern kitchen with stainless steel appliances, dining area, and a large balcony with views of the private landscaped backyard. The lower-level unit offers 1 bedroom, 1 full bathroom, and a fully equipped kitchen-perfect for rental or in-law arrangement. Shared

  Frank Hajhassan Realty One Group Heartland

  2214 N Mango Ave, Chicago, IL 60639
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  /50

  $1,899,000

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

  1717 W Huron St, Chicago, IL 60622

  Bold Design Meets Exceptional Comfort in This Expansive 7-Bedroom West Town Home Experience the perfect blend of modern luxury and wide floor plan in this striking 7 bedroom, 5.1 bathroom, 4-level city home situated on a rare 30-foot-wide lot in highly desirable West Town. From the moment you step into the grand marble foyer with a statement staircase and generous coat closet, the home's scale

  Tim Sheahan Compass

  1717 W Huron St, Chicago, IL 60622
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  /40

  $1,899,900

  • 5 Beds
  • 4 Baths
  • 5,991 Sq Ft

  1312 N Astor St, Chicago, IL 60610

  Rare Historic Gem on Prestigious Astor Street. Step into a piece of Chicago's architectural legacy with this remarkable corner rowhome, designed in 1887 by the iconic firm Burnham & Root. Originally one of four distinguished residences showcasing the bold elegance of the Richardsonian Romanesque style, this home sits next to 1310 N. Astor-once the personal residence of John Wellborn Root, a

  Todd Szwajkowski Baird & Warner

  1312 N Astor St, Chicago, IL 60610
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  /22

  $399,000

  • 5 Beds
  • 2 Baths
  • 1,735 Sq Ft

  4835 W Sunnyside Ave, Chicago, IL 60630

  Welcome to this solid home nestled on a desirable corner lot in a prime location! Featuring 3 bedrooms on the main floor and 2 more generous sized bedrooms upstairs, this versatile layout offers plenty of space to accommodate family or guests. This home has great bones and endless potential for your personal touch. Lovingly maintained by a long-time homeowner, this property is ready for it's next

  Ruby Park Coldwell Banker Realty

  4835 W Sunnyside Ave, Chicago, IL 60630
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  /32

  $1,175,000

  • 15 Beds
  • 10 Baths

  1347 E Hyde Park Blvd, Chicago, IL 60615

  BIG PRICE REDUCTION!!! ATTENTION REHABBERS AND REMODELERS! TREMENDOUS VALUE ADD PLAY! PRIME HYDE PARK LOCATION, CLOSE TO THEUNIVERSITY OF CHICAGO. THREE (3) MASSIVE APARTMENTS - 9 ROOM, 5 BEDROOM, 3 BATHROOM-2800 SQ FT EACH, PLUS A PARTIALLY FINISHED BASEMENT WITH8.5 CEILINGS, LARGE WINDOWS, AND A FULL BATHROOM. 11,250 TOTAL BUILDING SQ.FT. BUILDING IS VACANT AND NEEDS COSMETIC REHAB. PRICE

  Jerome Ettinger Ettinger Realty, Ltd.

  1347 E Hyde Park Blvd, Chicago, IL 60615
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  /43

  $229,000

  • 10 Beds
  • 5 Baths

  8401 S Brandon Ave, Chicago, IL 60617

  ABSOLUTE MONEY MAKER! Great investment opportunity for First-Time Buyers & Savvy Investors! Property Will need a gut rehab. Here's your chance to own a 4-unit property that can provide you with a positive CASH FLOW! This property has potential to profit over 100k in equity after some TLC. Layout features 4 2 beds with 1 bath. 12 Ft Ceilings. Unfinished basement with endless possibility for a

  Janina Farr Coldwell Banker Realty

  8401 S Brandon Ave, Chicago, IL 60617
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  /32

  $520,000

  • 5 Beds
  • 4 Baths

  3645 S Wood St, Chicago, IL 60609

  Welcome to this solid, well-maintained brick two-flat located in the heart of McKinley Park! This versatile property offers endless potential-perfect for owner-occupants, investors, or extended families. Property Highlights: Two spacious units with hardwood floors throughout. Large living rooms and generous bedrooms in both units. Finished basement ideal for extra living space, recreation, or

  Ivan Man Century 21 Realty Associates

  3645 S Wood St, Chicago, IL 60609
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  /36

  $499,000

  • 5 Beds
  • 2 Baths
  • 2,384 Sq Ft

  4042 N Kenneth Ave, Chicago, IL 60641

  This 2,384 SQFT single family home located in the heart of Old Irving Park offers a great combination of location, size, and versatile 2-unit layout that can easily adapt to your choice of use. First enter through the bright and sunny front porch with wall-to-wall windows and into the common foyer staircase room with charming butted door/window casing and separate entrances to each floor/unit.

  Dean Tubekis Coldwell Banker Realty

  4042 N Kenneth Ave, Chicago, IL 60641
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  /29

  $225,000

  • 6 Beds
  • 2 Baths
  • 2,100 Sq Ft

  10643 S Calhoun Ave, Chicago, IL 60617

  Calling All Large Families into this Spacious 6 Bedroom Home! This beauty is Perfect & waiting for You!! This well-maintained home exudes opportunity and space. Living room, Dining room & Eat in Kitchen with Stainless Steel Appliances & Granite Countertops, 6 Bedrooms and 2 Full Bathrooms. New Carpet, New Furnace & New Plumbing. This home has an enclosed sunporch & huge backyard for

  Tennille Ford Coldwell Banker Realty

  10643 S Calhoun Ave, Chicago, IL 60617
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  /48

  $7,150,000

  • 6 Beds
  • 7 Baths
  • 7,790 Sq Ft

  2043 N Clifton Ave, Chicago, IL 60614

  Unique opportunity, offering the ultimate city living with remarkable build and design, this perfectly located Lincoln Park home sits on a rarely available 62.5' wide lot. As you enter this modern and inviting abode, appreciate the extra wide rooms, floor to ceiling windows that spies your private garden oasis. Rebel House Design is credited with redesigning the main floor and new kitchen that

  Marco Mejia Lucid Realty, Inc.

  2043 N Clifton Ave, Chicago, IL 60614
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  /29

  $599,000

  • 7 Beds
  • 3 Baths

  256 W 23rd Place, Chicago, IL 60616

  A great investment building in hot and convenient location . Easy access to downtown, restaurants around , cross the street is Haines Elementary School. 1st floor has front unit and back unit. 1st Front has 2 bedrooms 1 bath with central Heat. 2023 new flooring, new cabinet and granite countertop. 1R has 2 bedrooms and 1 bath with radiator heat. 2nd floor is with 3 bedrooms and 1 bath with

  Rowena Cheng Richland Global Inc

  256 W 23rd Place, Chicago, IL 60616
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  /24

  $297,900

  • 5 Beds
  • 3 Baths
  • 2,400 Sq Ft

  8307 S Morgan St, Chicago, IL 60620

  This fully remodeled two-story home features five bedrooms, three bathrooms, a new roof and siding, smart technology including a wireless video doorbell, and brand-new central heating and cooling. The main floor offers a spacious open-concept living and dining area, a new kitchen with stainless steel appliances, two bedrooms, a full bathroom, and a laundry area with a new washer and dryer.

  Cassandra Sneed EXIT Strategy Realty

  8307 S Morgan St, Chicago, IL 60620
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  /13

  $260,000

  • 5 Beds
  • 2 Baths
  • 2,087 Sq Ft

  1942 E 74th St Unit 3B, Chicago, IL 60649

  CHECK OUT THIS FULLY FURNISHED CONDO! THIS BEAUTIFULLY UPDATED 5 BEDROOMS WITH HARDWOOD FLOORS, 2 FULL BATHROOMS, SEPERATE LIVING ROOM AND DINING ROOM, IN UNIT WASHER AND DRYER READY FOR YOU TO JUST MOVE IN... REALLY!! ALL THE FURNITURE IS STAYING ($10,000 WORTH) YOU CAN RENT IT OUT OR LIVE THERE! BEING SOLD "AS-IS" REALLY LOW TAXES, NO HOMEOWNER EXEMPTION, WHICH MEANS TAXES WILL BE LOWER. THE

  Nadia Meza Classic Realty Group Prestige

  1942 E 74th St Unit 3B, Chicago, IL 60649
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  /4

  $385,000

  • 7 Beds
  • 2 Baths

  7843 S Marquette Ave, Chicago, IL 60649

  Fully occupied brick 2-flat with month-to-month tenants, offering a great investment opportunity with immediate rental income. Each unit features a spacious layout and separate utilities. Well-maintained and conveniently located near public transportation, shopping, and other amenities. A solid addition to any investment portfolio-schedule your showing today.

  Anthony Kirkland Coldwell Banker Realty

  7843 S Marquette Ave, Chicago, IL 60649
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  /36

  $349,900

  • 8 Beds
  • 5 Baths

  2653 W 21st St, Chicago, IL 60608

  Massive 4 unit building with full basement. One block away from Pink line Metra station. Walking distance from groceries, shopping and restaurants. Multiple parking spaces in the back. All units are leased on a month-to-month basis. New Developmemt and construction in the area so ideal for investors or buyers looking to grow their portfolio.

  Freddie Ocampo Realty of America, LLC

  2653 W 21st St, Chicago, IL 60608
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  /29

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  6123 S Ellis Ave, Chicago, IL 60637

  6123 South Ellis: Your Campus Address for a Healthier, Greener Future. Experience the best of both worlds in this LEED Gold-rated, all-electric superhome. Ideally situated directly across from the University of Chicago, the Lab School, the Midway and moments from the picturesque lakefront and Obama Presidential Library Site, this residence offers unparalleled convenience and comfort. Step inside

  Wayne Beals Exit Strategy Realty / EMA Management

  6123 S Ellis Ave, Chicago, IL 60637
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  /9

  $924,900

  • 8 Beds
  • 4 Baths

  1810 N Wood St, Chicago, IL 60622

  EXCELLENT INVESTMENT OPPORTUNITY IN BUCKTOWN!! Great area within hot-trendy Bucktown. Four-Unit Rental Property with Garage. Basement can be easily converted to in-law suite or duplexed down for a fifth unit. Rents well below market rate; with a Remodel, great opportunity to significantly increase rents. Coin laundry & fenced-in back yard.

  Lance Schwimmer BAAN Properties, LLC

  1810 N Wood St, Chicago, IL 60622
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  /15

  $975,000 Open Sun 11AM - 1PM

  • 6 Beds
  • 3 Baths

  4019 N Tripp Ave, Chicago, IL 60641

  Welcome to an exceptional opportunity in the highly sought-after neighborhood of Old Irving Park. Completely gutted rehabbed, everything is new! Great for investment for renting out both units or living in one unit and rent out the other unit for additional income! This elegant 2 units family home located at 4019 North Tripp Avenue, Chicago, IL, presents a blend of comfort and sophistication,

  Mona Jee RE/MAX Premier

  4019 N Tripp Ave, Chicago, IL 60641
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  /18

  $262,900

  • 6 Beds
  • 3 Baths

  7713 S Cornell Ave, Chicago, IL 60649

  Great opportunity to own this two flat Brick apartment building - conveniently located near Stony Island Avenue - easy connection to downtown Chicago and the South Suburban areas! Both units have 2 bedrooms, Livingroom with decorative fireplace, Large Dining Room, Kitchen with oversized cabinets, stove and refrigerator. Hardwood Floors throughout! There is a basement with two extra rooms and a

  Tonya Corder Stages Real Estate LLC

  7713 S Cornell Ave, Chicago, IL 60649
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  /39

  $719,900

  • 8 Beds
  • 3 Baths

  5829 N Washtenaw Ave, Chicago, IL 60659

  Arcadia Terrace. Brick 2 Flat with finished basement. Both true 3br /1bth. Basement 2br /1bth. Newer electrical system. High efficiency hot water boiler, 75 gal. hot water tank. Separated storage room. Laundry room. Basement apartment with front & back entrance, flood control. Large back yard. 2 car brick garage plus space for side parking. Good for live in owners or great income for investor,

  Raza Hussain City Habitat Realty LLC

  5829 N Washtenaw Ave, Chicago, IL 60659
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  /45

  $699,900

  • 5 Beds
  • 3 Baths
  • 2,250 Sq Ft

  2656 W Coyle Ave, Chicago, IL 60645

  Welcome to this stunning five-bedroom, three-bath Jumbo Chicago Brick Bungalow, perfectly located on a corner lot along a peaceful, tree-lined street. The spacious first floor features a welcoming foyer, beautifully refinished hardwood floors, and elegant crown molding throughout. The eat-in kitchen is equipped with stainless steel appliances and a built-in butler's pantry. The sunny living room

  Acimina Bachas Duarte Realty Company

  2656 W Coyle Ave, Chicago, IL 60645
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  /46

  $574,900

  • 5 Beds
  • 3 Baths

  2617 W Crystal St, Chicago, IL 60622

  LEGAL brick 3 flat with 3 separate GFH, HWH, breakers. Decorative fireplaces in 2 units, 2 bedrooms & 1 bath on units 1&2 Gdn is 1 bed / 1 bath. Brick 2 car garage. Property functional, but needs work. Can be great for renovation or as an amazing SFH property. Near Humboldt Park and just N of amazing Division Street. This is a great opportunity - not to be missed!

  Rob Rubin RSR Management Inc

  2617 W Crystal St, Chicago, IL 60622
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  /52

  $1,200,000

  • 9 Beds
  • 5 Baths

  1727 W Roscoe St, Chicago, IL 60657

  Introducing a truly special property located in prime Roscoe Village neighborhood. Amazing opportunity to own a fully occupied 2-Flat + Coach House. FRONT BUILDING offers 2 units: 1st floor is 2 bedroom/1 bath and the 2nd floor is a huge duplexed up 4 bedroom/2 bath. In the back is a COACH HOUSE: 1st floor is a 1 bedroom /1 bath, 2nd floor is a huge duplexed up 2 bedroom/1 bath. Every unit has

  Neal Ratner Apartment and Home Seekers

  1727 W Roscoe St, Chicago, IL 60657
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  /12

  $884,000

  • 10 Beds
  • 4 Baths

  2307 S Leavitt St, Chicago, IL 60608

  Introducing a newly renovated gem in the heart of Chicago! This striking brick four-unit apartment building offers a blend of comfort, style, and convenience, perfect for the urban dweller or savvy investor. Featuring three 2-bedroom, 1-bathroom units and one expansive 3-bedroom, 1-bathroom unit, each apartment has been meticulously updated to cater to modern tastes and needs. Modern kitchens

  Angelo Labriola Sperry Van Ness

  2307 S Leavitt St, Chicago, IL 60608
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  /42

  $395,000

  • 9 Beds
  • 4 Baths

  2227 W 21st St, Chicago, IL 60608

  Located in the vibrant Pilsen area, this three-unit building with a coach house presents a promising investment opportunity. The property features three separate units, each with its own distinct layout, offering versatility for tenants. Additionally, the coach house provides potential for additional rental income or a private living space. While the property holds great investment potential, it

  Dalton Garcia RE/MAX Partners

  2227 W 21st St, Chicago, IL 60608
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  /44

  $4,249,000

  • 5 Beds
  • 6 Baths
  • 9,200 Sq Ft

  1352 N La Salle Dr, Chicago, IL 60610

  Stately mansion nestled on an oversized 33x 149 ft deep lot in the heart of prime Old Town. Rehabbed in 2016 to modernize the floor plan and restore the original masonry and most recently taken through a design refresh by Brianne Bishop Design, this magnificent mansion boasts approximately 9,200 sq ft of timeless elegance, featuring soaring 12-foot ceilings and exquisite craftsmanship throughout.

  Mark Icuss Compass

  1352 N La Salle Dr, Chicago, IL 60610
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  /23

  $244,900

  • 5 Beds
  • 2 Baths
  • 2,900 Sq Ft

  14020 S Green Bay Ave, Chicago, IL 60633

  Welcome to this beautiful Cape Cod, perfectly nestled on a spacious double-wide lot. With 4 generously sized bedrooms and 2 full baths, this home offers ample space for entertaining. Step inside to an inviting open-concept floor plan, where the warmth of a wood-burning fireplace creates the perfect focal point in the family room. The home features stunning hardwood floors that flow seamlessly

  Marge Kubascik Berkshire Hathaway HomeServices Executive Realty

  14020 S Green Bay Ave, Chicago, IL 60633
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  /4

  $599,000

  • 6 Beds
  • 2 Baths

  4979 N Kolmar Ave, Chicago, IL 60630

  Calling All investors and rehabbers! Well maintained brick 2 flat home on a very large lot...38X140. OR live on one floor and rent the other! Terrific location with easy access to all Metro areas of downtown Chicago. Wonderful green space to develop! Zoned RS 3! Very quiet street! Estate sale and property is being sold "as-is!" Hurry! This property will not last long!

  Martha Turner Baird & Warner

  4979 N Kolmar Ave, Chicago, IL 60630
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  /36

  $3,950,000

  • 6 Beds
  • 7 Baths
  • 4,366 Sq Ft

  1963 N Dayton St, Chicago, IL 60614

  Welcome to this exquisite French-inspired limestone masterpiece nestled on one of Lincoln Park's most prestigious and sought-after blocks. Offering 6 spacious bedrooms and 5.2 elegantly appointed bathrooms across four levels of luxurious living, this residence is a true architectural gem that blends timeless design with modern sophistication. Step inside to experience a home flooded with natural

  Marlene Rubenstein Baird & Warner

  1963 N Dayton St, Chicago, IL 60614
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  /14

  $339,000

  • 7 Beds
  • 3 Baths

  3320 W Monroe St, Chicago, IL 60624

  Spacious Graystone 2-Unit in East Garfield Park - Rare Opportunity with Incredible Space and Potential. Welcome to this well-maintained and spacious Graystone 2-unit, located in the rapidly developing East Garfield Park neighborhood. Boasting 7 total bedrooms and 3 full bathrooms, this property offers flexibility and comfort for both owner-occupants and investors alike. Each unit spans

  Faulkner Arnett RE/MAX Premier

  3320 W Monroe St, Chicago, IL 60624
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  /15

  $370,000

  • 5 Beds
  • 3 Baths

  6636 S Rhodes Ave, Chicago, IL 60637

  This is an outstanding opportunity to own a nicely updated 3 unit building in the desirable up and coming Woodlawn area! Conveniently located minutes from the University of Chicago and upcoming Obama Presidential Library. Plenty of kitchen cabinets and spacious rooms with a washer/dryer hookup in basement for further income. Low maintenance yard with 2 car garage. Easy access to expressway

  Chon Lemon Real People Realty

  6636 S Rhodes Ave, Chicago, IL 60637
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  /17

  $399,999

  • 9 Beds
  • 3 Baths

  7921 S Hermitage Ave, Chicago, IL 60620

  SOLID INVESTMENT!!! YOUR OPPORTUNITY TO OWN A BEAUTIFUL WELL TAKEN CARE OF 3 UNIT BUILDING. 3x INCOME AWAITS W/ MAJOR UPDATES IN CURRENT PROCESS. ALREADY INCLUDES SEPARATE HEATING UNITS AND WATER TANKS, NEWER WINDOWS THROUGHOUT, CERAMIC TILED KITCHENS AND BATHROOMS, BUZZER AND INTERCOM SYSTEM. COIN OPERATED WASHER AND DRYER INCLUDED FOR ADDITIONAL INCOME.

  Regina Wallace HomeSmart Connect LLC

  7921 S Hermitage Ave, Chicago, IL 60620
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  /9

  $1,224,000

  • 8 Beds
  • 4 Baths

  1454 W Ohio St, Chicago, IL 60642

  Rare, Classic, Solid Brick QUAD, in one of Chicago's hottest areas! Four updated units across the street from Bickerdike Square Park. Located close to hot Fulton Market District and very popular Division Street/Wicker Park neighborhoods. Steps to transportation, restaurants, bars, shopping, and all that urban living offers. Well maintained, owner-occupied building with FOUR fully leased rental

  Angela Frangias Frangias Realty

  1454 W Ohio St, Chicago, IL 60642

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