5-Bedroom Homes for Sale in Chicago, IL

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  /20

  $612,500

  • 5 Beds
  • 3 Baths

  4224 N Kimball Ave, Chicago, IL 60618

  Fantastic Albany Park location! Rehabbed 2 unit with a duplex up 3br 2ba unit rented at $2440 to 11/1/25 so perfect for owner occupants to move in and a beautiful backyard with a newer built (2019) 2 car garage which is rented month to month at $284 to a neighbor, tenants are awesome and happy to stay if you want to extend their leases. 2br 1ba unit is rented $1700. Furnaces/waterheaters and

  Henry Lazerow Fulton Grace Realty

  4224 N Kimball Ave, Chicago, IL 60618
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  /47

  $325,000

  • 5 Beds
  • 3 Baths

  10715 S Avenue G, Chicago, IL 60617

  Looking for the ideal investment property, or an owner-occupied income generating property? This charming, award-winning, 2-Unit Chicago-style brick bungalow is filled with character, charm and income potential! This captivating East Side home features recent updates including a new boiler system, electrical and plumbing improvements, tuckpointing, and 2nd floor windows, combined with timeless

  Dan Schlaack Coldwell Banker Realty

  10715 S Avenue G, Chicago, IL 60617
• 

  

  

  /31

  $561,000

  • 9 Beds
  • 3 Baths

  1532 S Homan Ave, Chicago, IL 60623

  Welcome to this exceptional, fully renovated 2Unit Greystone - an outstanding investment opportunity completed in 2025. Each of the units features 3 spacious bedrooms, a full bathroom, generous living and dining rooms, and an inviting enclosed back porch accentuated by soaring, high 10 ft ceilings. The interiors have been updated with a modern white palette, complemented by stylish 42-inch

  Yevhen Hurtovyi Realta Real Estate

  1532 S Homan Ave, Chicago, IL 60623
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  /30

  $300,000

  • 5 Beds
  • 2 Baths
  • 1,968 Sq Ft

  5145 S Troy St, Chicago, IL 60632

  TONS of space in this classic Chicago home! NOTE...Zoning will likely permit conversion to a 2 unit...but buyer needs to confirm with the City! 5 total bedrooms -- with the possibility of up to 7!!! If you have been looking for a "related living" property -- this is it! 2 kitchens and tons of extras! Recent improvements included: roof, siding and some mechanicals! The basement is HUGE and

  Jeffrey Gregory Realty Executives Success

  5145 S Troy St, Chicago, IL 60632
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  /42

  $1,475,000

  • 6 Beds
  • 4.5 Baths
  • 2,700 Sq Ft

  6316 N Magnolia Ave, Chicago, IL 60660

  Step into your private OASIS IN THE CITY with this truly unique single-family home-a stately 1895 Queen Anne residence nestled on a quiet, tree-lined street in the heart of Edgewater Glen. This architecturally significant home has been thoughtfully restored to preserve its original character, blending timeless charm with high-end modern updates. Offering over 2,700 square feet of living space,

  Curtis Hunt Coldwell Banker Realty

  6316 N Magnolia Ave, Chicago, IL 60660
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  /10

  $545,000

  • 15 Beds
  • 3 Baths

  4311 W Palmer St, Chicago, IL 60639

  This property features three legal units, with one vacant-perfect for owner-occupant financing options like FHA or conventional loans. Live in one and rent the others to generate immediate passive income. Walking distance to parks, schools, shops, and public transit. The area is steadily appreciating, adding long-term value. This won't last long on the market-contact the listing agent today to

  Anna Sophia Chacon Charles Rutenberg Realty of IL

  4311 W Palmer St, Chicago, IL 60639
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  /2

  $435,000

  • 9 Beds
  • 3 Baths

  1609 S Sawyer Ave, Chicago, IL 60623

  ATTENTION INVESTORS/DEVELOPERS: 2 ADJOINING GRAYSTONE BUILDINGS SELLING AS A PACKAGE (1607 AND 1609 S. SAWYER listing 12161956, each separate price, PREFERRED TO BE SOLD TOGETHER) TOTAL OF 18 BEDS, 6 BATHS, AND ROOM FOR EXPANSION, 1607 S. Sawyer has option to purchase adjacent double wide lot on 16th Street at FMV (confirm with city of Chicago). PRIME LOCATION ACROSS THE STREET OF DOUGLAS PARK

  Barbara Kieca Hometown Real Estate

  1609 S Sawyer Ave, Chicago, IL 60623
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  /2

  $445,000

  • 9 Beds
  • 3 Baths

  1607 S Sawyer Ave, Chicago, IL 60623

  ATTENTION INVESTORS/DEVELOPERS: 2 ADJOINING GRAYSTONE BUILDINGS SELLING AS A PACKAGE (1607 AND 1609 S. SAWYER listing 12161956, each separate price, PREFERRED TO BE SOLD TOGETHER) TOTAL OF 18 BEDS, 6 BATHS, AND ROOM FOR EXPANSION, 1607 S. Sawyer has option to purchase adjacent double wide lot on 16th Street at FMV (confirm with city of Chicago). PRIME LOCATION ACROSS THE STREET OF DOUGLAS PARK

  Barbara Kieca Hometown Real Estate

  1607 S Sawyer Ave, Chicago, IL 60623
• 

  

  /20

  $335,000

  • 5 Beds
  • 3 Baths

  7923 S Carpenter St, Chicago, IL 60620

  Welcome to this classic and well-maintained brick 2-flat, nestled on a quiet, tree-lined street in Chicago's Auburn Gresham neighborhood. This property offers the perfect opportunity for both savvy investors and owner-occupants looking to generate rental income. The fully screened-in porch and stately wrought iron fence offer curb appeal and peace of mind. Each spacious unit features generously

  Rebecca Martinez Berkshire Hathaway HomeServices Chicago

  7923 S Carpenter St, Chicago, IL 60620
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  /30

  $385,000

  • 5 Beds
  • 4 Baths
  • 2,796 Sq Ft

  629 E 87th Place, Chicago, IL 60619

  Step into this beautifully Chicago bungalow - a perfect blend of classic charm and modern comfort. This spacious home is ideal for families of all sizes, featuring an updated kitchen and bathroom that make everyday living a delight. Situated on an oversized lot, it offers generous indoor and outdoor spaces, perfect for entertaining guests or enjoying quiet evenings. You'll love the convenience

  LaToya McDaniel Coldwell Banker Realty

  629 E 87th Place, Chicago, IL 60619
• 

  

  /12

  $680,000

  • 9 Beds
  • 3 Baths

  461 W 28th Place, Chicago, IL 60616

  Remarkable 3 legal unit building (with coach house), fully renovated with open floor plans and within walking distance to Healy school and Mark Sheridan Math & Science Academy. All 3 apartments have gas forced air, central air, washer/dryer, hardwood floor, generous size bedrooms and open kitchen and living room.All units are fully occupied. .

  Qian Kun Chen Kale Realty

  461 W 28th Place, Chicago, IL 60616
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  /2

  $650,000

  • 6 Beds
  • 3 Baths

  943 N Fairfield Ave, Chicago, IL 60622

  **Gut Rehab Needed** Don't miss this rare chance to own a solid brick 3-unit building in the heart of red-hot Humboldt Park! Whether you're an investor looking to generate strong rental income or a savvy homeowner seeking a property with income potential, this is the perfect entry point. Each unit offers spacious layouts with tons of upside potential. The property also features a massive 4+

  Ryan Carney Dreams & Keys Real Estate Group

  943 N Fairfield Ave, Chicago, IL 60622
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  /49

  $759,900

  • 8 Beds
  • 3 Baths

  4100 W George St, Chicago, IL 60641

  THIS BEAUTIFUL ALL BRICK, WELL MAINTAIN BUILDING PRESENTS A GREAT INVESTMENT OPPORTUNITY. FIRST AND SECOND FLOOR FEATURES 3 BEDROOMS, HUGE LIVING-ROOM, BIG DINING ROOM, WITH HARDWOOD FLOORS, IN UNIT LAUNDRY. GARDEN UNIT FEATURES 2 BEDROOMS, LIVING ROOM, KITCHEN AND FULL BATHROOM, LAUNDRY ROOM WITH COIN OPERATED WASHER AND DRYER. LOCATED IN A DESIRABLE AREA WITH CONVENIENT ACCESS TO SHOPS,

  Sandra Ardon Su Familia Real Estate Inc

  4100 W George St, Chicago, IL 60641
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  /11

  $249,900

  • 9 Beds
  • 3 Baths

  6522 S Peoria St, Chicago, IL 60621

  Don't miss this spacious and well-maintained Greystone featuring two generous units plus a finished garden unit (not a legal apartment). Each unit offers a full dining room, eat-in kitchen, and separate utilities-providing privacy and convenience for all occupants. First Floor: Beautiful hardwood floors throughout, 3 comfortable bedrooms, and inviting living and dining spaces. Enjoy outdoor

  Andrea Crockwell Kale Realty

  6522 S Peoria St, Chicago, IL 60621
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  /32

  $6,950,000

  • 5 Beds
  • 6 Baths
  • 8,400 Sq Ft

  800 N Michigan Ave Unit 63, Chicago, IL 60611

  Remarkable opportunity to acquire full floor Park Tower penthouse at a truly outstanding value. Delivering panoramic 360 degree views of Chicago's world-class architecture and Lake Michigan, plus captivating sunrise to sunset views. This 5 bedroom 4.2 bath home spans 8,400 square feet perched atop the Park Hyatt Hotel, where first-class amenities are at your disposal: Spa, Indoor Pool, Fitness,

  Jeffrey Lowe Compass

  800 N Michigan Ave Unit 63, Chicago, IL 60611
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  /44

  $7,900,000

  • 7 Beds
  • 9 Baths
  • 12,250 Sq Ft

  209 E Lake Shore Dr Unit 14, Chicago, IL 60611

  Chicago's finest residence available for the first time. This incredible combination of two units offers a glorious 12,000+ square foot full-floor home in Benjamin Marshall's finest building on East Lake Shore Drive. Designed both for gracious family living and large-scale entertaining, this 7 Bedroom/7.2 Bathroom home speaks only of quality the moment you step off the elevator into the private

  Jeffrey Lowe Compass

  209 E Lake Shore Dr Unit 14, Chicago, IL 60611
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  /50

  $2,399,000

  • 6 Beds
  • 4.5 Baths
  • 5,900 Sq Ft

  1414 N Mohawk St, Chicago, IL 60610

  Welcome to one of Old Town's finest homes built on and oversized lot and surrounded by mature gardens of Boxwood, Limelight Hydrangea and Thorndale Ivy. Enter through its custom iron gates and be ready to fall in love. This home views like a story book with all of its special features and architectural details. Full limestone and brick construction originally built in 2012 and perfected

  Cara Buffa Berkshire Hathaway HomeServices Chicago

  1414 N Mohawk St, Chicago, IL 60610
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  /14

  $154,900

  • 5 Beds
  • 1.5 Baths
  • 1,298 Sq Ft

  10742 S Prairie Ave, Chicago, IL 60628

  5 bedroom & 1.5 bath brick bungalow. 3 bedrooms on main level and 2 on second level. Eat in kitchen with pantry. Unfinished basement. Enclosed porch, fenced yard and 2 car garage. This property is eligible nder the Freddie Mac FirstLook Initiative through 7/13/2025. Only owner occupant, non-profit and Neighborhood Stabilization Program (NSP) offers will be reviewed and considered during First

  Mera Kordic RE/MAX Premier

  10742 S Prairie Ave, Chicago, IL 60628
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  /14

  $895,000

  • 6 Beds
  • 6 Baths

  3648 S Paulina St, Chicago, IL 60609

  Ownership spared no expense in this exceptional fully renovated 4-unit property located at 3648 S Paulina in Chicago. This two-building offering includes a classic brick front building and a fully rehabbed rear coach house, each containing two thoughtfully designed units. No detail was spared in this high-end renovation, with all-new plumbing and electrical systems, brand-new kitchens and

  Angelo Labriola Sperry Van Ness

  3648 S Paulina St, Chicago, IL 60609
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  /23

  $399,900

  • 7 Beds
  • 4 Baths

  6917 S Aberdeen St, Chicago, IL 60621

  Recently updated extra large brick 2 flat on a quiet block. Modern finishes include - white kitchen cabinets, granite counter tops, ceramic tile backsplash, new SS appliances new light fixtures, mirrors, faucets...... 2 bedrooms on first floor and 3 bedrooms on the second. Finished basement duplexed to the first floor with additional 2 bedrooms and 1 bath creates extended living space. This house

  Alicja Grzych RE/MAX City

  6917 S Aberdeen St, Chicago, IL 60621
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  /19

  $110,000

  • 5 Beds
  • 3 Baths

  6527 S Marshfield Ave, Chicago, IL 60636

  Unlock the potential in this vintage brick 2 flat to make it your own. some rehab work has been started, but there are still extensive repairs to be made. Each unit has spacious formal dining room, and some hardwood floors. There is a 2 car detached garage, and a full unfinished basement.

  Barbara Thouvenell Baffoe P.R.S. Associates, Inc.

  6527 S Marshfield Ave, Chicago, IL 60636
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  /30

  $279,900

  • 5 Beds
  • 3 Baths

  7125 S Cornell Ave, Chicago, IL 60649

  Situated in the South Shore Neighborhood of Chicago & a short distance from South Shore Country Club & Obama Library! Well maintained 2-unit building! 1st floor features 2 Bedrooms, 1 Bath, dining & living room& back porch! 2nd floor features 3 bedroom, 1 bath dining & living room & back porch! Full, clean basement includes an additional bathroom & washer & dryer! Newer boiler! Perfect for owner

  Denise Hoekstra RE/MAX 1st Service

  7125 S Cornell Ave, Chicago, IL 60649
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  /36

  $269,000

  • 6 Beds
  • 2 Baths

  1721 W Steuben St, Chicago, IL 60643

  QUIET. EXTRAORDINARY. READY. Smart Buy in Morgan Park! Welcome to this well-maintained, fully-occupied 2-flat in the heart of the neighborhood, perfect for first-time multifamily buyers or experienced investors looking to build long-term wealth. Price reduced from $275k to $269k, a substantial cost savings for the right buyer! This property sits on 3 full city lots (that's the extraordinary part)

  Dona Crane EXIT Strategy Realty

  1721 W Steuben St, Chicago, IL 60643
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  /25

  $675,000

  • 9 Beds
  • 6 Baths

  2716 W Polk St, Chicago, IL 60612

  Investor's dream in the heart of the city WITH VERY strong CAP rate! This all-brick 3-flat is a prime opportunity with incredible income potential. Each spacious unit boasts 3 bedrooms and 2 baths, updated interiors, laundry in-unit. Rents are currently below market, offering room for increased profitability. The first and second floors feature soaring 9-ft ceilings, while the third floor

  Neveen Michael Keller Williams Infinity

  2716 W Polk St, Chicago, IL 60612
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  /25

  $800,000

  • 6 Beds
  • 3 Baths

  4652 N Magnolia Ave, Chicago, IL 60640

  TOTAL GUT REHAB. 2Bedrooms/1Bathroom/kitchen/Living Room on all 3 Floors Basement is unfinished and can be its own unit. The basement height is 6 ft appx. at it's highest point. The property also comes with a detached 2-car garage and fenced-in yard. Great uptown location on small 2 block run of Magnolia - close to the train, lake and shopping districts. Great rent potential and an area that is

  Ruqia Naqi Baird & Warner

  4652 N Magnolia Ave, Chicago, IL 60640
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  /37

  $365,000

  • 8 Beds
  • 8 Baths

  6455 S Marshfield Ave, Chicago, IL 60636

  Exceptional opportunity for investors. This Huge 2 Flat brick house includes an attached church/hall building that could easily be redeveloped. Parking lot fits 8-10 cars. Month to Month tenants bringing in a 4k monthly rent roll that could easily be increased. About 8 bedrooms with over 5 bathrooms in total. Full basement with loading dock. Endless possibilities, schedule your showing today!

  Maureen Chwarzynski Baird & Warner

  6455 S Marshfield Ave, Chicago, IL 60636
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  /22

  $2,199,999

  • 6 Beds
  • 6 Baths

  1420 W Fulton St, Chicago, IL 60607

  Fully occupied and completely renovated in 2015, this like-new historic brick 3-flat offers three identical 2 bed / 2 bath units with high-end finishes throughout. Features include quartz countertops, Bosch appliances, wine fridges, Kohler fixtures, wide-plank hardwood floors, Hunter Douglas blinds, fireplaces, in-unit laundry, and oversized Trex decks with gas hookups. Each unit is equipped with

  Jack Wiley Jameson Sotheby's International Realty

  1420 W Fulton St, Chicago, IL 60607
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  /25

  $400,000

  • 6 Beds
  • 4 Baths

  2322 S Trumbull Ave, Chicago, IL 60623

  RENOVATED Multi Unit! 1st Floor & 2nd Floor have the same layout; Formal Living Room & Dining Room with 2 Bedrooms. Garden Unit has 1n Bedroom. The Finished Attic also has one Bedroom. Lovely backyard and a 2 car garage. The rents are below market and should be higher. All Tenants are Month to Month.

  Jose Villasenor Realty of America, LLC

  2322 S Trumbull Ave, Chicago, IL 60623
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  /25

  $880,000

  • 8 Beds
  • 4 Baths

  1943 N Whipple St, Chicago, IL 60647

  Palmer Square/Logan Square- This updated apartment building sits on an oversized extra deep lot in an A+ location right off the 606 Bloomingdale Trail just 3.5 blocks from Palmer Square, 2 blocks from Humboldt Park and just steps to the Blue Line "L", Logan Square Farmer's Market, and all the wonderful restaurants and shops this fantastic neighborhood has to offer. 1st and 2nd floor apartments

  Michael Hall Baird & Warner

  1943 N Whipple St, Chicago, IL 60647
• 

  

  /22

  $315,000

  • 6 Beds
  • 2 Baths

  6239 S Bishop St, Chicago, IL 60636

  Two story building for a family or as an income property, located in West Englewood. Apartments were rehabbed in 2023. Currently no tenants. The building is located near public transportation and expressways. Ogden Park is just a five minute walk. Plenty of restaurants and stores nearby. The basement is unfinished but has plenty of space for a laundry room and storage.

  Jorge Lopez Charles Rutenberg Realty

  6239 S Bishop St, Chicago, IL 60636
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  /21

  $1,300,000

  • 10 Beds
  • 4 Baths

  600 N Pine Ave, Chicago, IL 60644

  A property truly like no other, step into timeless elegance and modern versatility with this extraordinary Queen Anne Victorian, thoughtfully converted into a sprawling 10-bedroom, 4-bathroom two-unit residence. Situated on a tree-lined street in Chicago's vibrant West Side, this one-of-a-kind property blends 19th-century charm with 21st-century comfort, perfect for multigenerational living or a

  Joseph Reyna Real People Realty

  600 N Pine Ave, Chicago, IL 60644
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  /50

  $2,599,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 4.5 Baths
  • 7,000 Sq Ft

  425 W Superior St, Chicago, IL 60654

  Exquisitely appointed and impeccably maintained, this 7000 SQFT home in River North's sought-after mansion district has it all: 5 bedrooms, 4.1 baths, 4 private terraces, a fully finished lower level, an attached two-car garage and an in-home elevator services all floors. Entertain on a grand scale with outdoor spaces and large recreation rooms on multiple levels. The first level features a

  Carrie McCormick @properties Christie's International Real Estate

  425 W Superior St, Chicago, IL 60654
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  /3

  $500,000

  • 5 Beds
  • 2 Baths
  • 3,248 Sq Ft

  3328 W Warren Blvd, Chicago, IL 60624

  Own a Rare Piece of Chicago History Don't miss this incredible opportunity to restore a true architectural gem. This massive Romanesque Revival Greystone, built circa 1890 by renowned architect Charles Weary, sits on an extra-wide 35' x 125' lot in red-hot East Garfield Park. Rich in character and potential, this rarely available historic mansion offers the perfect canvas for your vision.

  Cynthia Grunst-Bednarz Baird & Warner

  3328 W Warren Blvd, Chicago, IL 60624
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  /51

  $3,500,000

  • 5 Beds
  • 7 Baths
  • 6,500 Sq Ft

  34 E Bellevue Place, Chicago, IL 60611

  Quintessentially old Chicago on the outside and exquisitely modern on the inside, 34 E. Bellevue Pl. is a flawlessly renovated 5 bed/5.5 bath, 6500-square-foot, three-story single family home in the Gold Coast with a fully finished basement and three outdoor spaces including a roof deck. Located on a distinguished residential street just one block from the lakefront, an award-winning, luxury real

  Tim Salm Jameson Sotheby's Intl Realty

  34 E Bellevue Place, Chicago, IL 60611
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  /71

  $4,500,000

  • 6 Beds
  • 9 Baths

  446 W Huron St Unit 450, Chicago, IL 60654

  This masterfully designed 6-bedroom, 6-bathroom single-family home in Near North offers over 8,500 square feet of bespoke living space. Paired with four private outdoor areas, this is a rare opportunity to experience expansive, luxurious city living in one of Chicago's most sought-after neighborhoods. The residence is a true showcase of craftsmanship, scale, and thoughtful detail. The

  Emily Sachs Wong @properties Christie's International Real Estate

  446 W Huron St Unit 450, Chicago, IL 60654
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  /47

  $750,000

  • 6 Beds
  • 3 Baths

  2909 N Hoyne Ave, Chicago, IL 60618

  Welcome to this well-maintained and stylishly updated 2-flat with additional non-conforming basement unit, perfectly positioned on a full 25x125 lot in the heart of West Lakeview-less than a block from Hamlin Park! This high-demand location is surrounded by million-dollar homes and offers unbeatable access to outdoor and urban amenities! Inside, this turnkey investment features a total of 6

  Leigh Marcus @properties Christie's International Real Estate

  2909 N Hoyne Ave, Chicago, IL 60618
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  /31

  $454,900

  • 6 Beds
  • 3 Baths
  • 2,484 Sq Ft

  6137 W Giddings St, Chicago, IL 60630

  Welcome to this beautifully updated two-story home with a full finished basement, offering a total of eight bedrooms - six on the first and second floors, plus two additional bedrooms in the basement - along with a dedicated home office plus three modern full bathrooms, one on each level. The stylish kitchen is a chef's dream, showcasing granite countertops, brand-new white shaker cabinets, an

  Khawaja Nizamuddin White Stairs Inc

  6137 W Giddings St, Chicago, IL 60630
• 

  

  /10

  $525,000

  • 8 Beds
  • 3 Baths

  1826 S Drake Ave, Chicago, IL 60623

  This beautiful well kept graystone building in the heart of NORTH LAWNDALE can be your's! New furnaces, central air, and a new roof are in place for your comfort and peace of mind. This property is located just 6 miles west of downtown Chicago. It's seated in an up and coming community where there is ongoing community development and enhancement projects occurring. Public transportation via train

  Elliott Taylor Jr Realty Plus

  1826 S Drake Ave, Chicago, IL 60623
• 

  /2

  $189,999

  • 5 Beds
  • 2 Baths

  7142 S Lowe Ave, Chicago, IL 60621

  Nice affordable brick 2 flat on tree lined street. Featuring a 2 bedroom and a 3-bedroom unit. Hardwood flooring throughout living room, dining room, and bedrooms. The 2nd floor is in good condition, but the 1st floor and exterior of the property needs work. Once repaired, this building will generate good rental income. There is a full basement which is waiting for your expanded living ideas.

  Luis O. Rojas Turn Key Realty Solutions

  7142 S Lowe Ave, Chicago, IL 60621
• 

  

  /11

  $669,000

  • 6 Beds
  • 3 Baths

  6024 W Addison St, Chicago, IL 60634

  Fantastic investment opportunity to own a turnkey, income-producing property in the heart of Portage Park. This solid brick building features a legal two-flat plus a fully finished garden-level in-law apartment, offering excellent cash flow and flexibility for both investors and owner-occupants looking to decrease their mortgage expense by living in one unit and renting out the others. Located

  Dennis Degelmann Real 1 Realty

  6024 W Addison St, Chicago, IL 60634

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