5-Bedroom Homes for Sale in Chicago, IL

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  /45

  $1,200,000

  • 8 Beds
  • 4 Baths

  2421 W 21st Place, Chicago, IL 60608

  Attention Investors! Discover a rare Multi-Parcel Investment Opportunity on 21st Place! This is your chance to capture not just one, but three prime parcels in a sought after and fast-developing area! Located at 2421 (4-Unit Multi-Family), 2423 (Lot), and 2427 (Single-Family Home with Additional Lots), this prime package represents a smart and profitable opportunity for savvy investors and

  Richard Harnik First Midwest Realty LLC

  2421 W 21st Place, Chicago, IL 60608
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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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  /36

  $720,000

  • 9 Beds
  • 4 Baths

  2958 S Lowe Ave, Chicago, IL 60616

  Solid, income-producing multi-unit real estate seldom combines convenience, tenant appeal, and location as well as this corner-lot property at 2958 S Lowe Ave in Chicago. The building comprises four spacious apartments-two on the first floor (each 2 bedrooms, 1 bath) and two on the second floor (one 2-bedroom, 1 bath and one 3-bedroom, 1 bath)-each flowing naturally with hardwood flooring through

  Hugo Sanchez Realty of America, LLC

  2958 S Lowe Ave, Chicago, IL 60616
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  /49

  $799,900

  • 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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  /39

  $299,999

  • 15 Beds
  • 8 Baths

  5016 S Paulina St, Chicago, IL 60609

  Incredible opportunity in the rapidly evolving Back of the Yards neighborhood! 5016 S Paulina St offers a solid multi-unit investment with strong income potential in one of Chicago's up-and-coming areas. This property is ideal for seasoned investors looking to expand their portfolio or for buyers seeking a long-term hold in a high-growth market. This building is perfectly positioned for steady

  Fernando Rocha Jr. RE/MAX LOYALTY

  5016 S Paulina St, Chicago, IL 60609
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  /10

  $299,900

  • 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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  /31

  $3,195,000

  • 6 Beds
  • 5.5 Baths

  2678 N Orchard St, Chicago, IL 60614

  This is not your cookie-cutter Lincoln Park home. Situated on an oversized lot (25x145), this exceptional residence offers sophistication, functionality, and high design at every turn. With 12-foot ceilings on the main level, stunning walnut floors, and custom finishes throughout, every detail has been thoughtfully considered. A grand staircase and elevator provide seamless access across all

  Joanne Nemerovski Compass

  2678 N Orchard St, Chicago, IL 60614
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  /50

  $2,399,000 Open Sun 1PM - 3PM

  • 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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  /3

  $159,900

  • 5 Beds
  • 2 Baths

  738 W 87th St, Chicago, IL 60620

  Calling all Owner Occupants and Investors! Spacious 2-unit building situated on a double lot-ideal for additional yard space or future development. A great opportunity to live in one unit and rent the other or convert the property into a large single-family home. Property features: Separate utilities, Full basement, 2-car garage, Plenty of outdoor space Property is being sold AS-IS. Bring your

  Irene Perez Coldwell Banker Realty

  738 W 87th St, Chicago, IL 60620
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  /15

  $1,150,000

  • 7 Beds
  • 3 Baths

  2014 N Whipple St, Chicago, IL 60647

  A Charming 3-Unit in Logan Square! It is located a few blocks from the vibrant Palmer Park in the heart of Logan Square. It is perfect for multi-family living or investment and surrounded by the local charm of Logan Square. This beautiful building offers the perfect blend of modern comfort and vintage charm. The building breakdown is as follows Unit 1: Spacious 2-bedroom, 1-bathroom with new

  Siobhan Robinson MRS Real Estate Firm

  2014 N Whipple St, Chicago, IL 60647
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  /27

  $499,000

  • 6 Beds
  • 3 Baths

  3035 W Flournoy St, Chicago, IL 60612

  CLASSIC TOTALLY RENOVATED CHICAGO GREYSTONE 2FLAT!!! FEATURING 2 LARGE KITCHENS W/ QUARTZ COUNTERTOPS / ALL STAINLESS STEEL APPL'S / 3 BEDROOMS ON EACH FLOOR / 3 FULL BATHS / ENJOY THE CHARM OF HARDWOOD FLOORS THROUGHOUT / ALL NEW PLUMBING / NEW ELECTRIC / ALL NEW WINDOWS / ALL NEW HVAC W/ SEP HEATING / SEP ELECTRIC / SEPARATE UTILITIES / LARGE LAUNDRY ROOM / FULL FINISHED BSMT W/ POSSIBLE

  Maxine Dugar Charles Rutenberg Realty

  3035 W Flournoy St, Chicago, IL 60612
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  /26

  $769,000

  • 7 Beds
  • 3 Baths

  5814 N Campbell Ave, Chicago, IL 60659

  This classic extra-wide Chicago 2-flat sits on an oversized 33-ft wide lot that allows for truly expansive interiors with generously sized rooms and fantastic layouts with two 3-bedroom 1-bath apartments with dens, sunrooms and kitchens with walk-in pantries and a lower level 1BR apartment for a total of 7 bedrooms and 3 full baths. Offering the perfect blend of space, charm and versatility in a

  Michael Hall Baird & Warner

  5814 N Campbell Ave, Chicago, IL 60659
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  /34

  $849,000 Open Sun 12PM - 2PM

  • 5 Beds
  • 3 Baths

  2025 N Sawyer Ave, Chicago, IL 60647

  This beautifully updated frame 2-flat in prime Logan Square is a rare gem, featuring a duplexed-up owner's unit drenched in natural light, thanks to multiple skylights and an open, airy layout. The renovated owner's unit boasts a chef's dream kitchen, an expansive great room, and a private outdoor deck perfect for entertaining. Custom-built-ins, abundant closet space, and thoughtful touches

  Linda Sanchez Green Chicago Real Estate, LLC

  2025 N Sawyer Ave, Chicago, IL 60647
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  /14

  $164,900

  • 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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  /51

  $775,000

  • 7 Beds
  • 4 Baths

  2625 W Greenleaf Ave, Chicago, IL 60645

  Charming, vintage 3-flat building in Rogers Park features 3 units, each with 2 br + den and a LEGAL basement apartment with 1 br + a full bath. Unbeatable location. Rents are below market, offering an exceptional opportunity for investors looking for a high-potential rental property or owner occupants seeking additional rental income.

  Emilia Salonikas Coldwell Banker Realty

  2625 W Greenleaf Ave, Chicago, IL 60645
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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

  $409,900

  • 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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  /30

  $750,000

  • 6 Beds
  • 3 Baths

  1448 W Taylor St, Chicago, IL 60607

  Exceptional Investment or Rehab Opportunity - Classic 3-Unit Brick Building in the Heart of Little Italy! A rare find in one of Chicago's most historic and dynamic neighborhoods, this charming all brick 3-flat is perfectly situated just steps from vibrant Taylor Street in Little Italy. Nestled on a quiet, tree-lined block, this property offers the ideal combination of character, location, and

  Danielle Dowell Berkshire Hathaway HomeServices Chicago

  1448 W Taylor St, Chicago, IL 60607
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  /27

  $459,900

  • 5 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  7022 W 64th St, Chicago, IL 60638

  Welcome to this beautifully 2-story step ranch located in the desirable Clearing neighborhood! Offering three full levels of living space, this spacious home is perfect for families, or anyone needing room to grow. The main floor features a bright, inviting living room with a gas log fireplace, a full bathroom, a half bath, and a main-level bedroom with hardwood floors that flow seamlessly into

  Mayra Hernandez RE/MAX MI CASA

  7022 W 64th St, Chicago, IL 60638
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  /21

  $388,000

  • 6 Beds
  • 3 Baths

  3651 S Archer Ave, Chicago, IL 60609

  Fantastic investment or live-in opportunity in vibrant McKinley Park! Zoned C1-2 for both residential and commercial use, this property features two spacious units - each offering 3 bedrooms, 2 bathrooms, and in-unit laundry. Major improvements after seller purchase include porches, electrical upgrades, garage, roof, and code-required deconversion from 4 units. Interiors are primed for cosmetic

  Sally Haynes Keller Williams Rlty Partners

  3651 S Archer Ave, Chicago, IL 60609
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  /22

  $5,995,000

  • 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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  /31

  $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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  /46

  $4,050,000

  • 5 Beds
  • 7 Baths
  • 5,918 Sq Ft

  2209 N Seminary Ave, Chicago, IL 60614

  Seeing is believing. Step into this extraordinary double lot 48' by 115' home in Lincoln Park and be amazed. For your buyers that are looking for something different and unique. Beautiful five-bedroom 4.3 bath home with wonderful huge side yard and patio. Originally a single lot home, owners purchased the lot next door and did a major renovation incorporating the additional space. They

  Suzanne Gignilliat @properties Christie's International Real Estate

  2209 N Seminary Ave, Chicago, IL 60614
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  /36

  $275,000

  • 6 Beds
  • 2 Baths

  1721 W Steuben St, Chicago, IL 60643

  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. Priced at just $275k, this property sits on 3 full city lots - offering rare outdoor space, expansion potential , or added privacy. Each spacious unit features 3 bedrooms and 1

  Dona Crane EXIT Strategy Realty

  1721 W Steuben St, Chicago, IL 60643
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  /8

  $130,000

  • 5 Beds
  • 3 Baths

  4038 W Adams St, Chicago, IL 60624

  ***Attention all investors*** Add instant sweat equity to this 2-flat. This property needs a full renovation but has excellent potential. Sold strictly as-is. Seller does not provide survey. Cash or hard money only. Buyer will take subject to and remain responsible for vacating the Order of Permanent injunction recorded as doc #0926005097

  Anthony Disano Parkvue Realty Corporation

  4038 W Adams St, Chicago, IL 60624
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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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  /46

  $1,419,990

  • 10 Beds
  • 8 Baths

  1928 W 21st St, Chicago, IL 60608

  Modern 4-Unit in the Heart of Pilsen | Fully Renovated | Turnkey Investment or Live-In Opportunity Exceptional, fully renovated and permitted 4-unit property in the vibrant Pilsen neighborhood. This classic Chicago brick building blends historic charm with modern finishes, offering four thoughtfully designed apartments - each with 2 full baths and in-unit laundry: two spacious 3-bedroom/2-bath

  Bryan Esenberg Built Chicago

  1928 W 21st St, Chicago, IL 60608
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  /50

  $1,669,000

  • 6 Beds
  • 3.5 Baths
  • 3,615 Sq Ft

  1927 W Erie St, Chicago, IL 60622

  Welcome to this luxurious home, in Chicago's West Town neighborhood, with a modern design and exceptional comfort. Inside top-tier finishes include, custom millwork, wide-plank hardwood floors, 10' ceilings, 8' doors, LED lighting, ambient lighting, modern fixtures, and high end appliances. In the living room, floor-to-ceiling windows flood the space with natural light, complemented by a warm

  Jennifer Christopher Oak Leaf Realty

  1927 W Erie St, Chicago, IL 60622
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  /54

  $750,000

  • 8 Beds
  • 4 Baths

  5125 N La Crosse Ave, Chicago, IL 60630

  Drop in showing this Sunday (7/13/25) from 12:00 PM to 2:00 PM - don't miss this fantastic opportunity! Incredibly spacious and unique 2-flat with additional finished basement (in law unit), situated on an oversized 50' wide lot in the highly sought-after Jefferson Park/Forest Glen neighborhood. This property lives like a massive single-family home and offers tremendous versatility and income

  Julianna Gil Gil & Gil Group Corp.

  5125 N La Crosse Ave, Chicago, IL 60630
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  /23

  $240,000

  • 6 Beds
  • 2 Baths

  7042 S Carpenter St, Chicago, IL 60621

  Welcome to 7042 S Carpenter Street - A Solid Brick Two-Flat with Endless Potential! Nestled in a growing pocket of Chicago's Greater Englewood community, this classic brick two-flat is an ideal opportunity for owner-occupants and savvy investors alike. Each spacious unit features three bedrooms and one full bathroom, offering generous living space perfect for families or rental income The

  Nicole Wheatly EXIT Strategy Realty

  7042 S Carpenter St, Chicago, IL 60621
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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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  /50

  $3,199,000

  • 6 Beds
  • 5.5 Baths
  • 6,400 Sq Ft

  3830 N Wayne Ave, Chicago, IL 60613

  Elegant Southport Corridor Residence in the Blaine School District Situated on the coveted one-way stretch of Wayne Street, just steps from the vibrant Southport Corridor and within the highly sought-after Blaine School District, 3830 N. Wayne offers an extraordinary blend of timeless elegance, comfort, and functionality. Set on an oversized 37.5-foot-wide lot, this 6,400-square-foot home

  Klopas Stratton Team Jameson Sotheby's Int'l Realty

  3830 N Wayne Ave, Chicago, IL 60613
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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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  /35

  $1,249,000 Open Sun 11AM - 12:30PM

  • 5 Beds
  • 3.5 Baths

  3572 W Medill Ave, Chicago, IL 60647

  Don't miss the opportunity to own this stunning, fully renovated single family home in the heart of Logan Square. Meticulously remodeled, this 5 bedroom, 3.5 bathroom home pairs high end design with superior attention to detail. The entry opens to a bright and airy dining room featuring expansive wide-plank flooring, detailed custom millwork, and a gas fireplace with a quartz surround framed by

  Kimber Galvin Berkshire Hathaway HomeServices Chicago

  3572 W Medill Ave, Chicago, IL 60647
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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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  /58

  $900,000

  • 8 Beds
  • 5 Baths

  2531 W Lyndale St, Chicago, IL 60647

  Stunning rehabbed legal 4-unit in the Heart of Logan Square/West Bucktown! This multi-unit building is currently operating as a rehabbed 3-unit with a legal, 4th unit that is currently an unfinished garden apartment. This very large building was recently beautifully rehabbed and features a very large, rear addition and huge rehabbed 1ST FLOOR UNIT SIMPLEX + 2 DUPLEXED UNITS ON THE 2ND & 3RD

  Derek Disera Compass

  2531 W Lyndale St, Chicago, IL 60647
• 

  

  /36

  $545,000

  • 9 Beds
  • 4 Baths

  3810 W Ohio St, Chicago, IL 60624

  OPEN SUNDAY 07/27 11-12. 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

  William Mombela PROSALES REALTY

  3810 W Ohio St, Chicago, IL 60624

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