5-Bedroom Homes for Sale in Chicago, IL

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  /40

  $449,900

  • 6 Beds
  • 2 Baths

  6806 S Rockwell St, Chicago, IL 60629

  Fantastic opportunity in the Chicago Lawn area! This solid brick 2-unit property offers spacious layouts in both apartments, each featuring a bright living room, kitchen with dining area, 3 bedrooms, and 1 full bath. Appliances include refrigerator, stove, and microwave for added convenience. The unfinished basement provides additional storage space and includes laundry hookups. A brand-new 2-car

  Jose Martinez RE/MAX Mi Casa

  6806 S Rockwell St, Chicago, IL 60629
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  /14

  $829,000

  • 9 Beds
  • 6 Baths

  6349 S Maryland Ave, Chicago, IL 60637

  Set in exceptionally well-located Woodlawn on the confluence of Hyde Park walking distance to University of Chicago Campus. Built New 2022 Developer Owned and Operated. Expansive footprint, 3 flats all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Engineered floors, Fireplace, Curated Gallery of

  Karen Biazar North Clybourn Group, Inc.

  6349 S Maryland Ave, Chicago, IL 60637
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  /47

  $495,000

  • 9 Beds
  • 3 Baths

  6605 S Maryland Ave, Chicago, IL 60637

  Fully Rehabbed 2-Unit in Prime East Woodlawn! Welcome to this spacious two-unit building in East Woodlawn, near the University of Chicago and the Obama Presidential Center. Tons of new construction on Maryland Ave. The property has 9 bedrooms and 3 bathrooms, offering great living space and rental potential. Each unit has separate utilities. While there's no central air, both units have HVAC

  Phillip Younan Fulton Grace Realty

  6605 S Maryland Ave, Chicago, IL 60637
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  /38

  $500,000

  • 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

  Loreal Urso Baird & Warner

  4229 N Kedzie Ave, Chicago, IL 60618
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  /29

  $775,000

  • 8 Beds
  • 3 Baths

  4946 N Mozart St, Chicago, IL 60625

  LOCATION, LOCATION, LOCATION!!! DON'T MISS OUT ON THIS CHARMING CLASSIC JUMBO RED BRICK 2 FLAT WITH GREAT BONES IN THE DESIRABLE LINCOLN SQUARE/BUD LONG NEIGHBORHOOD!!! GREAT OPPORTUNITY FOR OWNER OCCUPIED OR SAVVY INVESTOR TO REMODEL TO YOUR PREFERENCE OR RENT OUT FOR POSITIVE CASH FLOW. LOCATED ON A QUIET RESIDENTIAL STREET NEAR TO RIVER PARK WITH A POOL, RIVER, KAYAK LAUNCH, TENNIS COURT,

  Sophath Sath PROSALES REALTY

  4946 N Mozart St, Chicago, IL 60625
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  /35

  $530,000

  • 9 Beds
  • 3 Baths

  3849 W Maypole Ave, Chicago, IL 60624

  Welcome to 3849 W Maypole Ave, a beautifully maintained three-story multi-unit property offering incredible space, functionality, and income potential! Each floor features 3 spacious bedrooms, a full bathroom, living room, dining area, and a fully equipped kitchen - ideal for owner-occupants or investors looking for rental income. Located right across from the iconic Garfield Park, enjoy

  Noemi Ochoa Luna Realty Group

  3849 W Maypole Ave, Chicago, IL 60624
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  /14

  $424,000

  • 7 Beds
  • 5 Baths

  38 W 78th St, Chicago, IL 60620

  Excellent Investment Opportunity in Chicago! This solid brick 3-unit building is a cash-flowing gem, perfect for both savvy investors and buyers ready to stop renting and start owning. The property features two spacious units with 3 bedrooms and 1.5 baths each, currently occupied with long-term, month-to-month tenants, providing immediate rental income. The lower-level unit includes 1 bedroom and

  Frank Montro Keller Williams Preferred Rlty

  38 W 78th St, Chicago, IL 60620
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  /72

  $425,000

  • 10 Beds
  • 5 Baths

  2711 S Hamlin Ave, Chicago, IL 60623

  Welcome to 2711 Hamlin, a rare legal 4-unit property in Chicago offering two separate two-unit buildings on an oversized lot. The front building features two spacious units along with a recently renovated full bathroom completed in 2023, plus an attic space that includes a separate one-bedroom apartment, providing flexibility for extended living or additional rental income. The rear building adds

  Ivan Blanco Baird & Warner

  2711 S Hamlin Ave, Chicago, IL 60623
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  /17

  $1,050,000

  • 6 Beds
  • 3 Baths

  3853 N Janssen Ave, Chicago, IL 60613

  Beautiful grey stone three flat on an amazing street in Lakeview just blocks away form Wrigley Field. Family owned since the 1920's. This building will be well suited for a developer or someone who knows how to bring a property back to its original glory.

  Thomas Marchetti Baird & Warner

  3853 N Janssen Ave, Chicago, IL 60613
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  /45

  $599,000

  • 5 Beds
  • 3 Baths

  3608 N Tripp Ave, Chicago, IL 60641

  Welcome to 3608 N Tripp Ave, a classic Chicago brick two-flat located on a quiet, tree-lined street in highly sought-after Irving Park. This well-maintained property sits on an extra-wide 5,304 sq ft lot and offers exceptional space, flexibility, and investment potential for both homeowners and savvy investors. With over 2,400 sq ft of above-grade living space and an additional 1,355 sq ft of

  Amanda Zick @properties Christie's International Real Estate

  3608 N Tripp Ave, Chicago, IL 60641
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  /30

  $475,000

  • 6 Beds
  • 3 Baths

  206 N Leamington Ave, Chicago, IL 60644

  Brick 2-Flat + Bonus Unit in Austin! Fully occupied and income-producing, this corner-lot property features two spacious 2BR units plus a finished 1BR garden apartment. The property sits on a corner lot with two separate PINS, fenced yard, and privacy landscaping that can be included for a packaged deal. Perfect for investors or owner-occupants looking to offset their mortgage. Prime location

  Keona Robinson Real People Realty

  206 N Leamington Ave, Chicago, IL 60644
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  /28

  $1,595,000

  • 5 Beds
  • 4 Baths
  • 4,400 Sq Ft

  2305 N Commonwealth Ave Unit 1N, Chicago, IL 60614

  Incredible vintage masterpiece! Rare opportunity in East Lincoln Park! This exquisite five-bedroom, four-bath duplex offers approximately 4,400 square feet and truly lives like a single-family home. Nestled in an intimate boutique building, just steps from the Lincoln Park Zoo, North Pond, and Lake Michigan, it blends timeless character with generous space and modern amenities. Built in the early

  Joanne Nemerovski Compass

  2305 N Commonwealth Ave Unit 1N, Chicago, IL 60614
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  /47

  $1,175,000

  • 8 Beds
  • 5 Baths

  1817 N Lawndale Ave, Chicago, IL 60647

  Boutique Eco & Smart Apartments. All Electric Building, providing modern day efficiency. Eco-efficiency: Ultra-efficient wi-fi controlled multi-zone artic heat pump and air-conditioning. Luxury oversized Low-E casement windows, insulation, and building wrap & a refreshed building facade. Wifi-controlled designer ceiling fans in every room with remote dimmers. Widely available street parking in

  Andy Andrade Kale Realty

  1817 N Lawndale Ave, Chicago, IL 60647
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  /67

  $579,000

  • 6 Beds
  • 3 Baths

  2117 N Mulligan Ave, Chicago, IL 60639

  Welcome home. Gorgeous and spacious property rehabbed 2 Unit property home. The home features a beautiful kitchen with an open floor plan concept with granite countertops, tile backsplash bran newer custom build white cabinets which kitchen leads to a 4-season sunroom, perfect for an office space or just an extra storage room/ 2 nice bedrooms in the 1st level, spacious living room & living room

  Silvia Hernandez RE/MAX City

  2117 N Mulligan Ave, Chicago, IL 60639
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  /58

  $5,750,000

  • 6 Beds
  • 8 Baths
  • 9,740 Sq Ft

  1019 N Wolcott Ave, Chicago, IL 60622

  Prepare to be captivated by one of Chicago's most extraordinary real estate offerings: The Lincoln Street Bath House, a jaw-dropping fusion of historic grandeur and cutting-edge luxury. One of only four surviving municipal bath houses in the city, this rare architectural masterpiece-originally built between 1894 and 1918-has been transformed into a spectacular private residence that radiates

  Jennifer Mills Jameson Sotheby's Intl Realty

  1019 N Wolcott Ave, Chicago, IL 60622
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  /19

  $385,000

  • 8 Beds
  • 3 Baths

  8909 S Houston Ave, Chicago, IL 60617

  BEWARE OF RENTAL SCAMS. UNITS NOT ON MARKET FOR RENT. Welcome to this 3-unit property, designed for modern living and savvy investing. The layouts provide spacious living areas with plenty of natural light, Modern fixtures throughout, Updated kitchen and bathrooms, Washer and dryer hook-up in each unit. This building is ideal for owner-occupiers seeking rental income or investors looking for a

  Elaine Dubois Abram Property Management & Real Estate LLC

  8909 S Houston Ave, Chicago, IL 60617
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  /30

  $320,000

  • 5 Beds
  • 2.5 Baths
  • 1,454 Sq Ft

  12053 S Michigan Ave, Chicago, IL 60628

  Totally remodeled Spacious and inviting beautiful two-story home features 5 bedrooms, 2.5 baths, and a fully finished basement-perfectly designed for comfortable family living. With room to grow, entertain, and relax. This gorgeous home is a warm and welcoming space just waiting for the right family to call it home.

  Dora Wooden Illinois Star, LTD

  12053 S Michigan Ave, Chicago, IL 60628
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  /10

  $349,900 Open Sat 1PM - 3PM

  • 5 Beds
  • 2 Baths

  4910 W Gladys Ave, Chicago, IL 60644

  Welcome to this stunningly updated Chicago classic brick 2-unit property, where timeless elegance meets modern upgrades. This meticulously maintained residence boasts rich oak hardwood floors throughout, exuding warmth and sophistication in every corner. The second-floor unit features 3 spacious bedrooms and 1 full bathroom, offering abundant natural light and thoughtful layout. The first-floor

  Rob Wilczynski Luna Realty Group

  4910 W Gladys Ave, Chicago, IL 60644
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  /13

  $1,200,000 Open Fri 12PM - 1PM

  • 6 Beds
  • 3 Baths

  2433 W Dakin St, Chicago, IL 60618

  Bell School District Alert! Hot new listing of a double brick, Chicago-style, two-flat, with a finished basement, front entry, side driveway, and extra wide (35' RS-3) lot with beautiful yard and garden. Lovingly maintained and owned by the same family for over 50 years. Improvements in 2025 include: New roof silver-coat, new boiler, cedar outdoor decks, tuckpointing and chimney rebuilt. Newer

  Joe Wilcox The Wilcox Company

  2433 W Dakin St, Chicago, IL 60618
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  /27

  $479,900

  • 9 Beds
  • 3 Baths

  4636 S Keating Ave, Chicago, IL 60632

  Introducing an exceptional multi-unit property in Garfield Ridge, featuring two well-appointed units along with a convenient in-law suite in the basement. The first-floor apartment boasts three spacious bedrooms and a modern bathroom, recently updated with new flooring, stylish lighting fixtures, and an elegant backsplash in the kitchen. Second floor is a 3 bed 1 bath that was updated in 2022.

  Erick Escobedo Realty of America, LLC

  4636 S Keating Ave, Chicago, IL 60632
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  /2

  $279,000

  • 6 Beds
  • 2 Baths

  Unlisted Address

  Here is an opportunity to obtain a 2flat building in the very desirable Austin area. Just blocks away from Columbus Park, schools, public transportation and I290 expressway. Only minutes to the nearest suburb. Property has good bones and loads of potential. Features generous space with 3brs and 1full bath in each unit. Full unfinished basement and 2car garage. Great for investors, rehabbers or

  Sharon Moore Real People Realty

  Unlisted Address
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  /35

  $440,000 Open Sat 1PM - 3PM

  • 6 Beds
  • 3 Baths

  4317 S Sawyer Ave, Chicago, IL 60632

  Don't miss this once-in-a-lifetime investment opportunity at 4317 S Sawyer Ave-perfect for a new or seasoned landlord! This solid brick 2-flat features two spacious units, each with 2 bedrooms and 1 bathroom, plus a full basement and a huge, partially finished attic offering great potential for storage or future expansion. The property includes 3 electric and 3 gas meters for separate utilities.

  Valeria Guerrero Su Familia Real Estate Inc

  4317 S Sawyer Ave, Chicago, IL 60632
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  /36

  $419,000

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

  2728 W 39th Place, Chicago, IL 60632

  Look no more. Come to check out this solid and spacious span three level brick home. It boasts 2 spacious beds and 1.5 bath on the main floor, and a master en-suite located in the attic. The furnished basement offers an in-law unit with 2 additional bedrooms and 1 bath, providing ample living space. It equips with central heating and central air. Over the years, the home has undergone many

  Angela Kwan Goodland Realty Inc.

  2728 W 39th Place, Chicago, IL 60632
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  /24

  $590,000

  • 7 Beds
  • 3 Baths

  2511 N Laramie Ave, Chicago, IL 60639

  SOLID AND WELL MAINTAINED BRICK 3 FLAT IN BELMONT CRAGIN AREA. GOOD SIZE LIVING ROOM W/WESTERN EXPOSURE. 3 ORIGINAL BRS (1ST & 2ND FLOOR). CT BATH, EAT-IN KITCHEN, HARDWOOD FLOORS UNDER CARPETING, ENCLOSED PORCH. NEWER BOILERS/HEATERS 2017-2020, TEAR OFF ROOF 2017. FRONT IRON FENCE. EXTRA WIDE LOT, BRICK 2.5 CAR GARAGE PLUS POSSIBLE ADDITIONAL PARKING SPACE, NICE GARDEN, CEMENT PATIO. SEPARATE

  John Kulesza Beaulieu Real Estate

  2511 N Laramie Ave, Chicago, IL 60639
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  /53

  $6,500,000

  • 5 Beds
  • 4.5 Baths
  • 6,800 Sq Ft

  1964 N Burling St, Chicago, IL 60614

  This East Lincoln Park crown jewel marries history and architectural significance with luxurious interiors. The home is located on a double 50 x 123.4 lot. This Italianate-style residence at 1964 North Burling was originally built in 1883 as a single-family home on a former nursery and horse truck farm. It is part of the Sheffield National Register Historic District and, significantly, is rated

  Colette Cachey Smithburg @properties Christie's International Real Estate

  1964 N Burling St, Chicago, IL 60614
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  /23

  $149,900

  • 5 Beds
  • 3 Baths

  10901 S Michigan Ave, Chicago, IL 60628

  Beautiful Single Family Residence with basement and outdoor parking, being used as a 2 Unit property. 1 Bedroom in first floor Unit, and 4 Bedrooms in second floor Unit. Seller is addressing zoning for this property, it should be a 2 Unit. Great investment opportunity, live in one and rent the other! Subject to prior offer cancellation.

  Michael Olszewski Area Wide Realty

  10901 S Michigan Ave, Chicago, IL 60628
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  /17

  $895,000

  • 8 Beds
  • 4 Baths

  4241 N Laramie Ave, Chicago, IL 60641

  4241 N. Laramie Avenue is a legal four-unit building in Portage Park with (4) 2-bedroom/1-bath apartments plus a non-conforming garden unit. Units feature hardwood floors, laminate countertops, a mix of white/stainless appliances, and two surface parking spots. All apartments are boiler-heated except Unit 2S, which has individual HVAC. The property is located just north of Irving Park Road and

  Ryan Blake Nara Advisors, Inc

  4241 N Laramie Ave, Chicago, IL 60641
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  /22

  $825,000

  • 6 Beds
  • 4 Baths

  3847 W School St, Chicago, IL 60618

  Everything is new from 2019 - no deffered maintenance - perfect armchair investment in Avondale. 80,400 in gross lease income (both leases end 5/31/26-they are lined up for the next owner). Unit 1 is a 4 bed duplex down, and the second unit is a 3 bed duplex up-all finishes and mechanicals from 2019. A 30-foot-wide lot offers great floor plans and a massive backyard. This is perfect for owner

  Klopas Stratton Team Jameson Sotheby's Int'l Realty

  3847 W School St, Chicago, IL 60618
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  /45

  $324,900

  • 5 Beds
  • 3 Baths
  • 2,690 Sq Ft

  8444 S Essex Ave, Chicago, IL 60617

  Welcome to this spectacular 5 bedroom and 3 full bathroom home with a beautiful finished basement just minutes from Lake Michigan beach. This beautifully updated home offers an abundance of space and natural light throughout. The gleaming hardwood floors welcome you in the spacious living room with a stunning fireplace and a grandiose bay window with wonderful views of the beautiful tree lined

  Arturo Olivares Grandview Realty LLC

  8444 S Essex Ave, Chicago, IL 60617
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  /22

  $249,000

  • 8 Beds
  • 3 Baths

  8253 S Brandon Ave, Chicago, IL 60617

  Solid income producing potential! Currently set up as 3 Units, this building offers a competitive cap rate, making it a great opportunity for an owner occupant or a smart investor. Units 1F & 1R offer 2BR/1BA each, with an open floorplan and hardwood floors. Kitchen and baths feature tasteful espresso cabinets, granite counters, and tile finishes. Unit 2 is a huge 4BR/1BA apartment that occupies

  Andria Hernandez Compass

  8253 S Brandon Ave, Chicago, IL 60617
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  /25

  $229,900

  • 5 Beds
  • 1 Bath
  • 985 Sq Ft

  6742 S Honore St, Chicago, IL 60636

  Great, and spacious home waiting for you to call home. Home features Five bedrooms. Beautiful kitchen with Granite Countertops, and SS appliances. A modern bathroom. Hardwood floor in the living and dining room. Unfinished basement but with lots of potential for more living space. One car garage, and a good-sized yard. Come and show!

  Yazmin Orozco St Joseph's Real Estate LLC

  6742 S Honore St, Chicago, IL 60636
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  /9

  $949,999

  • 6 Beds
  • 3 Baths

  1728 N Francisco Ave, Chicago, IL 60647

  Unique multi units occupy by family for many years nicely maintain an oversized lot with newer garage and extra parking spaces for 2 or more cars, 606 trail right in your back yard by Western and California, located between Wicker Park and Humboldt Park. First floor unit has Central heat. All units are well maintain lots of improvements you wont be disappointed.

  Yolanda Arroyo Chicagoland Brokers, Inc.

  1728 N Francisco Ave, Chicago, IL 60647
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  /30

  $769,000

  • 6 Beds
  • 4 Baths

  2727 N Artesian Ave, Chicago, IL 60647

  Sunny 3-flat in a prime Logan Square location near the Bucktown/Avondale border. Beautifully maintained and updated throughout the years by the same family. First-floor unit has been updated and features soaring 9-foot ceilings, coffered ceilings in the dining room, gorgeous hard wood floors, open concept living & dining room, kitchen has beautiful cabinets & backsplash, French doors open to

  Kathy Jewusiak Berkshire Hathaway HomeServices Chicago

  2727 N Artesian Ave, Chicago, IL 60647
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  /61

  $1,500,000

  • 10 Beds
  • 9 Baths

  2710 N Artesian Ave, Chicago, IL 60647

  Turnkey 4-Unit in Prime Logan Square. Rare opportunity to own a well-maintained 4-unit building on a quiet, tree-lined street in one of Chicago's most sought-after neighborhoods. Each unit has its own PIN, offering potential for future condo conversion. Strong unit mix: (2) 3-bed / 2-bath units and (2) duplex-downs (2 bed / 2 bath and 2 bed / 2.5 bath). All units feature separate utilities,

  Travis Wallace Jameson Sotheby's International Realty

  2710 N Artesian Ave, Chicago, IL 60647
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  /5

  $219,000

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft

  15 E 118th St, Chicago, IL 60628

  Priced to SELL!! LOW TAXES (No exemption applied)... Five spacious bedrooms, high ceilings and three full bathrooms, including a master suite that features an impressive 8x6 walk-in closet. Second floor laundry room and a lounge area perfect for relaxation or private family space. This home is a perfect blend of style, comfort, and modern amenities, ready to welcome you with open arms. Agents

  Monique Giles Illinois Real Estate Partners

  15 E 118th St, Chicago, IL 60628
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  /45

  $519,900 Open Thu 2:30PM - 4PM

  • 8 Beds
  • 3 Baths

  7245 S Washtenaw Ave, Chicago, IL 60629

  RARE TO FIND UPDATED MULTI-UNITS BUILDING WITH THREE SEPRATE NEW HIGH EFFICENCY FURNACE,DUCT WORK,A/C CONDENSORS.THREE NEW KITCHENS WITH SOLID WOOD CABINETS,SOFT CLOSE FEATURE AND EXOTIC QUARTZ COUNTER TOPS.NEW STAINLESS STEEL APPLIANCES PER UNIT,THREE NEW BATHROOMS WITH POLISHED QUARTZ FINISHED TILE,NEW VANITY AND FIXTURES.ALL FAMLIY ROOMS WITH DECOR FIRE PLACE.NEW CONCRETE WALK WAY.BRICK TWO

  Salvador Gonzalez RE/MAX Mi Casa

  7245 S Washtenaw Ave, Chicago, IL 60629
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  /19

  $810,000

  • 9 Beds
  • 4 Baths

  2036 W Birchwood Ave, Chicago, IL 60645

  BEAUTIFUL ROGERS PARK BRICK 3-FLAT with parking pad in rear! Each Unit has 3 BRs 1 BTH totaling 9 beds 3 baths. Enjoy LOTS of Space WITH DINING ROOMS + FRONT And BACK SUNROOMS (use back sunroom for an extra bedroom), with outside space to add your chairs and grill! HVAC, Central A/C, Stainless Steel Appliances, Separate Utilities for Each Unit. Coin Laundry in Basement with an Additional

  David Williamson Choice Realty Group Inc.

  2036 W Birchwood Ave, Chicago, IL 60645
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  /42

  $475,000

  • 7 Beds
  • 3 Baths

  4122 W Cermak Rd, Chicago, IL 60623

  Step into this timeless Chicago 3-flat, where stunning original woodwork meets thoughtful modern upgrades. Perfect for both investors and owner-occupants, the property features two tenant-occupied units and one owner-occupied unit. Garden & 1st Floor Units: Each with 2 bedrooms and 1 full bath 2nd Floor Unit: 3 spacious bedrooms and 1 full bath The building offers plenty of charm with large

  Shandra Phillips Village Realty, Inc.

  4122 W Cermak Rd, Chicago, IL 60623
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  /32

  $379,900

  • 6 Beds
  • 4 Baths

  2737 W 38th Place, Chicago, IL 60632

  Your Search Ends Here - Turnkey 2-Unit in Unbeatable Location! This beautifully updated 2-unit is the total package! Each unit offers 3 spacious bedrooms, 1.5 baths, stunning renovated kitchens, brand-new flooring, and sun-filled living rooms with oversized closets. Enjoy both front and rear entrances, a private fenced yard perfect for grilling and entertaining, plus a 2-car garage for added

  Melania Reyes RE/MAX Mi Casa

  2737 W 38th Place, Chicago, IL 60632
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  /38

  $275,000

  • 8 Beds
  • 6 Baths

  17 N Austin Blvd, Chicago, IL 60644

  Endless Potential in Historic Austin - All-Brick 3-Unit with 4-Car Garage This solid, all-brick 3-unit property has been in the family for years and is now ready for its next chapter. Fully gutted and primed for renovation, it offers an incredible opportunity for investors or owner-occupants alike. Highlights include: Brand new roof and recent tuckpointing Each main floor offers

  David Thomas Blue Door Dave Inc

  17 N Austin Blvd, Chicago, IL 60644

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