5-Bedroom Homes for Sale in Cook County IL

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  /30

  $375,000

  • 5 Beds
  • 2 Baths

  1611 Saint Charles Rd, Maywood, IL 60153

  Great investment opportunity, both units are rented on a month-to-month basis. Property is being Sold As Is.

  David Diaz Realty of America, LLC

  1611 Saint Charles Rd, Maywood, IL 60153
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  /17

  $365,000

  • 7 Beds
  • 4 Baths

  9152 S Halsted St, Chicago, IL 60620

  Prime Investment Alert - Cash-Flowing 4-Unit with Bonus Lot! Turnkey, income-producing brick 4-unit building with 100% occupancy and a proven rental history. Two units are on active leases, while two are month-to-month, giving you both immediate cash flow and flexibility to raise rents. The property also includes an adjacent lot - perfect for expansion or outdoor amenities that can boost income

  Dana Nolan Keller Williams ONEChicago

  9152 S Halsted St, Chicago, IL 60620
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  /31

  $724,999

  • 6 Beds
  • 3 Baths

  5759 N Bernard St, Chicago, IL 60659

  Hard to find Legal 3-Flat in the Heart of Albany Park This beautifully updated 3-flat offers spacious, modern living in one of Chicago's most diverse and vibrant neighborhoods. The first and second-floor units feature hardwood floors throughout, updated kitchens and baths, and generous closet space in each bedroom. The finished basement includes 2 bedrooms and 1 bathroom-ideal for in-law

  Mohammed Iftikhar Guidance Realty

  5759 N Bernard St, Chicago, IL 60659
• 

  

  

  /17

  $110,000

  • 6 Beds
  • 2 Baths

  7159 S Winchester Ave, Chicago, IL 60636

  Packed with potential, this solid two-unit is an ideal value-add project for investors, rehabbers, or experienced homeowners looking to create long-term equity. Each level offers a spacious, flexible layout ready for your redesign-update kitchens and baths, refresh flooring, and modernize mechanicals to command strong rents or set up a live-in/lease-one "house hack." A full basement provides

  Israel Dominguez Realty of America, LLC

  7159 S Winchester Ave, Chicago, IL 60636
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  /49

  $720,000

  • 9 Beds
  • 3 Baths

  5169 S Michigan Ave, Chicago, IL 60615

  Seller offering 10,000 in credits towards the buyer's closing cost with a list price offer! 5169 S Michigan Ave is a well-maintained 3-unit rehabbed building in vibrant Washington Park. Each of the three spacious units have been updated with modern kitchens featuring quartz countertops and stainless steel appliances, plus larger back decks perfect for everyday use or entertaining.

  Phillip Dixon Compass

  5169 S Michigan Ave, Chicago, IL 60615
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  /61

  $489,000

  • 6 Beds
  • 4 Baths

  5125 S Elizabeth St, Chicago, IL 60609

  Beautifully updated and well-maintained, this frame 3-flat is a great opportunity for both investors and owner-occupants. The first and second floors each offer 2 bedrooms and 1 bathroom, while the spacious third floor features 3 bedrooms, 1 bathroom, and a large family room-perfect for additional living space or entertaining. All units have been updated with modern kitchens that include granite

  Ronald Ohr Avenue 1 Realty Group

  5125 S Elizabeth St, Chicago, IL 60609
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  /16

  $459,000

  • 6 Beds
  • 2 Baths

  4863 N Kilpatrick Ave, Chicago, IL 60630

  Investor Opportunity in North Mayfair! Discover this charming 2-flat situated on an oversized lot in the highly desirable North Mayfair neighborhood. Nestled on a quiet, tree-lined street, this property offers a rare combination of space, location, and potential. Just minutes from shopping, dining, public transportation, and expressway access. Each spacious unit features generous living and

  Peter Deja Cross County Realty Inc.

  4863 N Kilpatrick Ave, Chicago, IL 60630
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  /32

  $415,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  1971 W 97th St, Chicago, IL 60643

  Welcome to 1971 W 97th st, This solid brick 5 bed 2 bath Chicago Bungalow in the Beverly neighborhood is awaiting you. Step through the front door to be welcomed by beautiful hardwood floors that run throughout the 1st floor. High ceilings and oversized windows allow for tons of natural light. You will fall in love with all the trim detail and clean lines. The first floor boasts 2 bedrooms and a

  Steve Budzik ICandy Realty LLC

  1971 W 97th St, Chicago, IL 60643
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  /30

  $425,000

  • 6 Beds
  • 4 Baths

  817 W 51st Place, Chicago, IL 60609

  Beautifully Renovated 2-Flat in Englewood! This impeccably renovated property offers the perfect blend of modern comfort and investment potential. Each spacious unit features a chef's kitchen with quartz countertops, top-of-the-line stainless steel appliances, and sleek modern tile. Luxury vinyl plank flooring runs throughout, complemented by stylish bathrooms and cozy electric fireplaces in both

  Richard Lomax Fulton Grace Realty

  817 W 51st Place, Chicago, IL 60609
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  /52

  $4,800,000

  • 6 Beds
  • 7 Baths
  • 8,549 Sq Ft

  640 Hill Rd, Winnetka, IL 60093

  Greeley and Winnetka schools!! Welcome to Meadowpool - a distinguished Tudor residence nestled on a meticulously landscaped and wooded one acre lot. Built in 1923, the home's design exudes classic Tudor charm with stucco and stone exterior and a slate roof. The entryway is adorned with leaded glass windows and rich woodwork and leads to a charming living room featuring a limestone fireplace. The

  Deborah Richwine @properties Christie's International Real Estate

  640 Hill Rd, Winnetka, IL 60093
• 

  

  /18

  $429,000

  • 9 Beds
  • 4 Baths

  625 N Monticello Ave, Chicago, IL 60624

  Beautiful Humboldt Park Discounted 2-Flat. Unit 1 is duplexed W/ 6 bedrooms & 3 bathrooms. Unit 2 has 3 bedrooms 1 bathRm.Gorgeous kitchens w/granite countertops, and hardwood floors. Ceramic tile updated Bathrms .Separate Heating & Electric. 2 exterior parking spaces. RENTAL INCOME on 2nd fl. Property Sold "AS IS " Agents check Brokers Remarks . Property already discounted. Send POF , Send Offers

  Angel Morales Golden City Realty, Inc.

  625 N Monticello Ave, Chicago, IL 60624
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  /55

  $549,900

  • 6 Beds
  • 4 Baths

  2101 48th Ct, Cicero, IL 60804

  Future Homeowners & Community Investors! Looking to call a striking and lavishly new rehabbed home yours? Welcome to this stunning BRAND NEW 2 unit multi-family located in the vibrant and rising town of Cicero. This freshly gut rehab has been remodeled down to the studs (2025) in order to provide a premium luxury living experience. Each unit has 3 bedrooms / 1.5 baths with separate living and

  Edgar Diaz Duarte Realty Company

  2101 48th Ct, Cicero, IL 60804
• 

  

  /26

  $475,000

  • 6 Beds
  • 3 Baths
  • 3,000 Sq Ft

  1703 N Monticello Ave, Chicago, IL 60647

  This generously sized home offers versatile living across multiple levels. The main floor features a sunlit living room, formal dining room, a well-appointed kitchen, one bedroom, and a full bathroom. Upstairs, you'll find three additional bedrooms and another full bathroom. An additional third-floor space provides extra room for storage or potential expansion. The finished basement includes a

  Joel Halperin Baird & Warner

  1703 N Monticello Ave, Chicago, IL 60647
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  /30

  $444,900

  • 6 Beds
  • 2 Baths

  4032 W Wilcox St, Chicago, IL 60624

  Welcome to this beautiful two-story Building!! Both floors incorporate spacious living and dining room areas with incredible lighting. You'll find yourself in a fully renovated bathroom with brand new flooring. First floor has two bedrooms and Second floor has 3 bedrooms. Remodeled kitchens which feature stainless steel appliances. In addition, the basement is unfinished for your Ideas. As you

  Rocio Rodriguez Solaris Enterprises Inc

  4032 W Wilcox St, Chicago, IL 60624
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  /29

  $575,000

  • 7 Beds
  • 3 Baths

  4629 W Parker Ave, Chicago, IL 60639

  Beautifully updated Belmont Cragin 2-unit brick building with a full finished basement, just blocks from major stores, groceries, and public transit. Each unit has its own HVAC system, the roof was coated 2 years ago, and windows have been updated.The first floor offers 2 bedrooms, 1 bathroom, hardwood floors, formal dining and living rooms, and spacious bedrooms. The second floor features 2

  Luz Gutierrez Garcia RE/MAX LOYALTY

  4629 W Parker Ave, Chicago, IL 60639
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  /36

  $585,000

  • 5 Beds
  • 2.5 Baths
  • 3,219 Sq Ft

  11854 Swilly Ct, Orland Park, IL 60467

  Have you been searching for a spacious 5-bedroom, 2.5 bathroom home with a finished basement in the highly desired Orland Park School District? Do you dream of living on a quiet cul-de-sac, tucked away from the hustle and bustle of La Grange Road and the mall? Welcome to 11854 Swilly Ct. - a home that checks all the boxes! From the moment you step inside, you'll be captivated by the light-filled,

  Denise Manning Keller Williams Infinity

  11854 Swilly Ct, Orland Park, IL 60467
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  /32

  $1,495,000

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

  3045 W Ardmore Ave, Chicago, IL 60659

  Once-in-a-lifetime opportunity! Absolute perfection and attention to detail! This stately Tudor home has been completely refurbished and reimagined with no detail overlooked and no expense spared! A designer showcase of stunning architectural details with high-end, custom finishes throughout. Versatile floorplan with several bedroom and in-home office space options. Supreme location right

  Sophia Worden Berkshire Hathaway HomeServices Chicago

  3045 W Ardmore Ave, Chicago, IL 60659
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  /67

  $1,150,000

  • 5 Beds
  • 3.5 Baths

  4853 N Leavitt St, Chicago, IL 60625

  Stunning and spacious 5-Bedroom Single Family Home in Lincoln Square, close to Winnemac Park! This updated home offers the perfect blend of character, space, and modern comfort. With 5 bedrooms up and 3.1 baths, it provides incredible flexibility for today's lifestyle. The main level is ideal for entertaining, featuring a formal living room, elegant dining room, and a thoughtfully updated kitchen

  Scott Curcio Baird & Warner

  4853 N Leavitt St, Chicago, IL 60625
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  /44

  $549,500

  • 5 Beds
  • 2 Baths

  5054 W Hutchinson St, Chicago, IL 60641

  Great Location in Portage Park, Long term owner . Well maintained building , One 3 bed 1 bath on top floor, 2 bed one bath on main level , both units have private enclosed rear porchs , Full basement , two car brick garage. Walking distance to 6 corners , great transportation area.

  John Fleming Baird & Warner

  5054 W Hutchinson St, Chicago, IL 60641
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  /11

  $6,900,000

  • 5 Beds
  • 8 Baths

  1438 N Dearborn St, Chicago, IL 60610

  Behind this classic historic Gold Coast facade lies an extraordinary reinvention. Meticulously stripped to the shell and rebuilt just two years ago as a custom residence for the current owners by Environs Development, this is a rare Gold Coast resale that lives like new construction - thoughtfully reimagined with a floorplan that caters perfectly to modern living without a single compromise. In a

  Kevin Wood @properties Christie's International Real Estate

  1438 N Dearborn St, Chicago, IL 60610
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  /40

  $600,000

  • 8 Beds
  • 3 Baths

  3734 W Sunnyside Ave, Chicago, IL 60625

  Massive. Versatile. Rare. This extra-wide 37-foot lot holds an expanded two-flat with an oversized three-car garage and endless possibilities. The owner's duplex-down boasts 5 bedrooms, two full kitchens, hardwood floors, and a sprawling living/dining room perfect for big gatherings. Upstairs, the bright 3 bed unit + den/office/nursery) features huge living and dining rooms, a dishwasher-equipped

  Kevin Hinton Keller Williams ONEChicago

  3734 W Sunnyside Ave, Chicago, IL 60625
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  /40

  $1,495,000

  • 5 Beds
  • 4 Baths

  1335 Asbury Ave, Evanston, IL 60201

  Don't miss this beauty! With 12' ceilings and beautiful original wood molding and hardwood floors throughout, this stunning home is move in ready. The layout of the house is such that rooms can be repurposed based on your lifestyle. The entry with its arched doorway steps leads up to a foyer with a stunning staircase. On one side you will find the immense living room complete with wood burning

  Lynn Briskin @properties Christie's International Real Estate

  1335 Asbury Ave, Evanston, IL 60201
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  /46

  $467,500

  • 5 Beds
  • 2 Baths

  941 Marengo Ave, Forest Park, IL 60130

  Charming Two-Flat on an Extra-Wide Lot - Your Home, with Built-In Income Potential! This rare 60-foot-wide lot offers a unique opportunity to enjoy the space, comfort and yard of a single-family home while benefiting from rental income. Family-owned and lovingly maintained, this two-unit property is ideal for an owner-occupant looking for a long-term tenant, short-term rental/Airbnb or

  Tabitha Murphy Berkshire Hathaway HomeServices Chicago

  941 Marengo Ave, Forest Park, IL 60130
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  /17

  $450,000

  • 11 Beds
  • 3 Baths

  8942 S Baltimore Ave, Chicago, IL 60617

  Looking for a cash-flowing 3-unit? Look no more! This property was renovated in 2023 and has since been fully occupied by tenants and managed by a professional property management company. All it needs now is for you to put a little TLC back into the building from normal wear and tear. Property is AS-IS but in 2023 all new plumbing, electrical, and mechanicals. The property has two occupied units

  Pamela Mondane Coldwell Banker Realty

  8942 S Baltimore Ave, Chicago, IL 60617
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  /36

  $539,999

  • 9 Beds
  • 4 Baths

  3810 W Ohio St, Chicago, IL 60624

  TERRIFIC INVERSTMENT HAS BECOME AVAILABLE! HUGE 3 UNIT BUILDING PLUS A FULL FINISHED BASEMENT. HIGHLY UP AND COMING HUMBOLDT PARK NEIGHBORHOOD, ONLY MINUTES FROM THE GARFIELD CONSEVAROTY/PARK. PROPERTY FEATURES ALL SEPARATE FORCED AIR HEATING, ALL SEPARATE UTILITIES, NEWER REAR PORCH, AND HUGE ALL CEMENTED REAR PARKING AREA FOR UP TO 4 CARS. LOW TAXES TO MAXIMIZE YOUR ROI. COME SEE YOUR NEW

  William Mombela PROSALES REALTY

  3810 W Ohio St, Chicago, IL 60624
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  /15

  $380,000

  • 6 Beds
  • 3 Baths

  2315 W 21st St, Chicago, IL 60608

  Pilsen 2 unit. The 2nd floor is duplex with the attic and offers a 3 bedrooms (possible 4 bedrooms) with 2 full bathrooms, living room, dining and modern kitchen with granite counter tops, hardwood floors throughout main floor and carpet on the attic. 1st floor offers a 3 bedrooms, living room and dining and kitchen. The rear has parking space for 4 cars.

  Oscar Campos RE/MAX Mi Casa

  2315 W 21st St, Chicago, IL 60608
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  /11

  $175,000

  • 5 Beds
  • 2 Baths
  • 1,509 Sq Ft

  6939 S Ada St, Chicago, IL 60636

  SPACIOUS 5 BED 2 BATH HOME WITH HARDWOOD FLOORING. LARGE REAR PORCH AND YARD AREA WITH PARKING PAD. POTENTIAL FOR A 6TH BEDROOM ON THE 2ND FLOOR. UNFINISHED BASEMENT AWAITS YOUR CREATIVE IDEAS. SUPER LOW TAXES UNDER 700 PER YEAR

  Joseph Konney Top Care Realty LLC

  6939 S Ada St, Chicago, IL 60636
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  /14

  $549,000

  • 5 Beds
  • 3 Baths

  9011 Bronx Ave, Skokie, IL 60077

  Opportunity knocks! This well-maintained 2-flat in a highly desirable Skokie location is now available for the first time in more than 20 years. Perfectly situated within walking distance to downtown Skokie, shopping, dining, and the Yellow Line, this property offers an outstanding investment or owner-occupant opportunity. Unit 1 features a spacious 2BD/1BA layout, while Unit 2 offers a generous

  Jose Hernandez Coldwell Banker Realty

  9011 Bronx Ave, Skokie, IL 60077
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  /9

  $310,000

  • 5 Beds
  • 2 Baths

  328 27th Ave, Bellwood, IL 60104

  Outstanding opportunity to own this fully rented 2-flat in Bellwood! This property sits on a DOUBLE lot (separate PIN) on a quiet street. Both units are rented month to month allowing flexibility for new owner. Spacious layouts and lots of natural sunlight. Second floor was updated with vinyl floors and paint, has 3 bedrooms, first floor is in a good shape too and has 2 bedrooms. Unfinished

  Joanna Nytko HomeSmart Connect LLC

  328 27th Ave, Bellwood, IL 60104
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  /81

  $2,999,000

  • 5 Beds
  • 4 Baths

  116 N Willard Ct Unit PH01, Chicago, IL 60607

  BEST VALUE PENTHOUSE WITH PRIVATE ROOFTOP IN THE WEST LOOP! LAST 2 UNITS REMAIN IN THIS DEVELOPMENT. Tucked away on a quiet side street in the heart of Chicago's vibrant West Loop, this stunning new-construction duplex penthouse offers an unparalleled blend of luxury, space, and privacy. Spanning two expansive levels with over 1700 sq ft of private rooftop deck, this 5-bedroom + den/office,

  Sabina Szura Baird & Warner

  116 N Willard Ct Unit PH01, Chicago, IL 60607
• 

  

  /23

  $950,000

  • 6 Beds
  • 3 Baths

  4850 N Rockwell St, Chicago, IL 60625

  Introducing this classic 3 unit brick building...situated on a lovely tree-lined street in the heart of Lincoln Square. Fully occupied and well-maintained, this building offers a tremendous investment opportunity. All 3 units are 2 bedroom / 1 bathroom layouts and are very spacious in size (almost 1400 sqft). Each apartment gets great natural light and has a separate living room, dining room and

  Owen Duffy Fulton Grace Realty

  4850 N Rockwell St, Chicago, IL 60625
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  /32

  $515,000

  • 9 Beds
  • 3 Baths

  1510 S Hamlin Ave, Chicago, IL 60623

  Beautifully updated brick 2-flat with a finished non-conforming garden unit located in the heart of Chicago's North Lawndale neighborhood.Recent updates in 2017 Roof, complete tear-off w/ new membrane w/ 1/2" insulation in 2017 with fresh silver coating applied in 2022,All Low-E Argon gas double hung windows.Basement floor dug w/new sewer line,2022 new glass block windows,2/3 of basement has

  Clemente Lopez Chicagoland Brokers, Inc.

  1510 S Hamlin Ave, Chicago, IL 60623
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  /50

  $375,000

  • 5 Beds
  • 2 Baths
  • 1,600 Sq Ft

  6540 S Vernon Ave, Chicago, IL 60637

  Beautifully updated home situated on a spacious double lot, offering plenty of outdoor space and ample street parking. This 5-bedroom, 2-bath property features generous living, dining, and family rooms, providing flexibility and comfort for everyday living. For added convenience, a washer and dryer are included. With its updates and roomy layout, this home is move-in ready and perfect for a

  Erika Villegas Re/Max In The Village

  6540 S Vernon Ave, Chicago, IL 60637
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  /33

  $1,399,000

  • 5 Beds
  • 5 Baths
  • 7,167 Sq Ft

  4858 W Chase Ave, Lincolnwood, IL 60712

  Stunning, One-of-a-Kind Custom-Built Brick Home perfectly situated in one of the area's most sought-after neighborhoods. Pride of ownership is evident throughout. Soaring 10-foot ceilings span all three levels, complemented by beautifully crafted specialty ceilings in nearly every room. Two fireplaces are cleverly positioned to be enjoyed from five separate spaces, enhancing the home's warmth

  Connie Aparcedo Coldwell Banker Realty

  4858 W Chase Ave, Lincolnwood, IL 60712
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  /47

  $545,000

  • 5 Beds
  • 3 Baths

  3623 S Emerald Ave, Chicago, IL 60609

  Welcome to 3623 S. Emerald Avenue, a beautifully updated brick two-flat in the heart of Bridgeport. With its classic Chicago facade, bold yellow entry doors, and modern interiors. This property is ideal for both investors and owner-occupants seeking style, comfort, and income potential. Each unit offers a modern layout with tall ceilings, hardwood floors, and oversized windows that fill the space

  Brian Aurelio @properties Christie's International Real Estate

  3623 S Emerald Ave, Chicago, IL 60609
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  /14

  $849,900

  • 8 Beds
  • 4 Baths

  8836 Bronx Ave, Skokie, IL 60077

  Incredible 4-unit building in Skokie featuring four spacious two-bedroom, one-bath units approximately 1,000 sq ft each. Several units have been recently updated with modern kitchens and bathrooms. Hardwood floors throughout the building add to its appeal. Each unit offers an HVAC system, including Ac's for added convenience. Great school districts. Ample parking available in the back for

  Harris Ali Sky High Real Estate Inc.

  8836 Bronx Ave, Skokie, IL 60077
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  /38

  $1,350,000

  • 8 Beds
  • 4 Baths

  1431 N Maplewood Ave, Chicago, IL 60622

  Stunning Greystone 3-Flat with spacious units, a 2-car garage, and strong in-place rental income. Fully updated with new mechanicals, plumbing, and electrical, this turnkey property ensures low maintenance for years ahead. Unit 1 (3BD/2BA Duplex-Down, $3,200/mo) features hardwood floors, a granite/stainless kitchen, private deck, spa-like marble baths, radiant heated concrete floors on the lower

  Tim Stassi Dwell One Realty

  1431 N Maplewood Ave, Chicago, IL 60622
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  /39

  $4,250,000

  • 6 Beds
  • 6.5 Baths
  • 6,200 Sq Ft

  2730 N Magnolia Ave Unit 32, Chicago, IL 60614

  Enjoy living on an extra wide, 40' lot on this beautiful Lincoln Park tree lined block. This newer construction custom home feels very current and well as totally timeless. An inviting front porch is the perfect place to relax and also welcomes you into this classically designed space. The width can be felt immediately and allows for grand room sizes and perfect spaces for entertaining as well as

  Emily Sachs Wong @properties Christie's International Real Estate

  2730 N Magnolia Ave Unit 32, Chicago, IL 60614
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  /26

  $239,900

  • 5 Beds
  • 2 Baths
  • 2,200 Sq Ft

  1144 Grant Ave, Chicago Heights, IL 60411

  CAN BE USED AS A HUGE SINGLE FAMILY HOUSE OR A CASH FLOWING 2-UNIT IN CHICAGO HEIGHTS! LOW TAXES! CORNER LOT. BRAND NEW ASPHALT DRIVEWAY This gut rehabbed home was renovated up and down from A-Z! With a total of 5 bedrooms, 2 baths and an unfinished walk out basement there is nothing like this for the price! This home boasts a brand new roof, windows, facia soffits and brand new gutters will be

  Kenneth Hoffman Hoffman Realtors LLC

  1144 Grant Ave, Chicago Heights, IL 60411
• 

  

  /9

  $250,000

  • 6 Beds
  • 2 Baths

  4643 W Monroe St, Chicago, IL 60644

  This Two unit brick property with 2 Car garage offers great potential! Both units are occupied by MTM tenants! Both Units need to be updated. First floor has 3 bedrooms and 1 bathroom. Second floor offers 3 bedrooms and 1 bathroom. Both units include separate living and dining rooms plus back porch. Full unfinished basement has a separate entrance and exit along with a kitchen, bathroom, and

  Autoria Morrow A Morrow Properties

  4643 W Monroe St, Chicago, IL 60644

Showing Results 161 - 200, Page 5 of 18