3,832

Chicago, IL Homes for Sale under $500,000

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  • /16

    $275,000

    • 1 Bed
    • 1 Bath

    20 N State St Unit 1013, Chicago, IL 60602

    Rare opportunity to own a truly unique industrial penthouse loft in one of the Loop's most distinctive residential buildings-a converted warehouse unlike any other in the neighborhood. Located on the top floor, this exceptional residence features dramatic soaring ceilings, the highest in the building, creating an expansive and airy living space rarely found in downtown Chicago. Character and

    Matt Laricy Americorp, Ltd

    20 N State St Unit 1013, Chicago, IL 60602
  • /21

    $264,900

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    1221 N Dearborn St Unit 812N, Chicago, IL 60610

    Sleek, stylish, and updated, this Gold Coast duplex one-bedroom lives like a private retreat in the heart of the city. Two levels of living space with beautiful red oak hardwood floors in a natural finish, complemented by a rebuilt hardwood staircase and modern lighting that gives the home a clean, contemporary feel. The redesigned kitchen features quartz countertops, stainless steel appliances,

    Camie Cirrincione Redfin Corporation

    1221 N Dearborn St Unit 812N, Chicago, IL 60610
  • /23

    $299,990

    $25K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 1,505 Sq Ft

    633 S Plymouth Ct Unit 702, Chicago, IL 60605

    Live the authentic loft lifestyle in the historic Pope Building, ideally located in the heart of Printer's Row! This oversized 1-bedroom, 1.5-bath concrete loft offers approximately 1,500 square feet of open living space with soaring 12-foot ceilings, beautiful hardwood floors, and oversized windows that flood the home with natural light. The expansive open-concept floor plan is perfect for both

    Matt Laricy Americorp, Ltd

    633 S Plymouth Ct Unit 702, Chicago, IL 60605
  • /23

    $219,000

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft

    4250 N Marine Dr Unit 531, Chicago, IL 60613

    Welcome to 4250 N Marine Dr #531, a spacious and thoughtfully updated one-bedroom home in the iconic Imperial Towers. This oversized open floor plan creates a comfortable layout with generous room sizes, wood laminate flooring, newer windows, excellent natural light, and updated window treatments installed in 2023. Throughout the home, you'll find abundant closet space and smart storage

    Trevor Hughes Paper Plane Realty

    4250 N Marine Dr Unit 531, Chicago, IL 60613
  • /18

    $219,999

    • Studio
    • 1 Bath
    • 570 Sq Ft

    345 N Lasalle St Unit 1109, Chicago, IL 60654

    Welcome to the perfect River North studio at The Sterling Private Residences, offering an unbeatable location and a full suite of amenities. This bright and inviting home features engineered flooring, oversized windows that fill the space with natural light, and an open kitchen with a breakfast bar overlooking the living area. The unit has been thoughtfully updated with new lighting, a newer

    Matt Laricy Americorp, Ltd

    345 N Lasalle St Unit 1109, Chicago, IL 60654
  • /42

    $399,999

    Pending
    • 4 Beds
    • 2 Baths
    • 1,700 Sq Ft

    2623 N Melvina Ave, Chicago, IL 60639

    MULTIPLE OFFERS RECEIVED -- Please submit your Highest and Best offer by Monday @ 5PM. You do not want to miss this charming Bungalow style Single Family Home in the heart of Belmont Central, on an extra wide - 33 foot- lot! The home is nestled between the Montclare and Belmont Cragin neighborhoods, LESS THAN ONE BLOCK from Riis Park Tennis Courts & in close proximity to the Brick Yard! The

    Joshua Irizarry Fulton Grace Realty

    2623 N Melvina Ave, Chicago, IL 60639
  • /24

    $449,900

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,264 Sq Ft

    6028 N Oriole Ave, Chicago, IL 60631

    Welcome to this classic all-brick Cape Cod in desirable Norwood Park. This 3-bedroom, 1.1-bath home offers a sun-drenched living room and seperate dining room, creating a warm and welcoming atmosphere for everyday living and entertaining. Charming details include original build-ins, original hardwood floors, trims/mouldings. The country style kitchen provides plenty of room and features updated

    Rafal Szypcio Coldwell Banker Real Estate Group

    6028 N Oriole Ave, Chicago, IL 60631
  • /48

    $425,000

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

    4846 S Tripp Ave, Chicago, IL 60632

    Three finished levels. Five bedrooms. Three full baths. One classic Chicago bungalow. Main floor features two bedrooms, one full bath, a separate dining room, and a kitchen with a walk-in pantry. Many of the home's original details have been preserved, including crown molding, built-ins, accent sconces, and hardwood floors. An enclosed rear porch provides flexible space for a home office, reading

    Beata Kozakiewicz Sterling Group Inc

    4846 S Tripp Ave, Chicago, IL 60632
  • /19

    $359,900

    • 3 Beds
    • 2.5 Baths
    • 1,630 Sq Ft

    7002 W Belden Ave, Chicago, IL 60707

    Beautifully updated and modern 3-Bed/2.5-Bth tri-level townhome ready for new owners! The main level features a bright, open floor plan with a spacious living and dining area showcasing gorgeous hardwood floors, a cozy fireplace and sliders leading to your private balcony. The living room flows seamlessly into the eat-in kitchen, complete with crisp white cabinets and stainless steel appliances.

    Marina Collazo Redfin Corporation

    7002 W Belden Ave, Chicago, IL 60707
  • /21

    $225,000

    • 1 Bed
    • 1 Bath
    • 683 Sq Ft

    440 N Wabash Ave Unit 2907, Chicago, IL 60611

    Experience exceptional city living in this bright and spacious 1-bedroom, 1-bath condo in the heart of River North. Floor-to-ceiling windows fill the home with natural light and showcase stunning south-facing views of the skyline and Riverwalk. The kitchen features stainless steel appliances and granite countertops, while wood laminate flooring runs throughout the space. Generous closet space

    Matt Laricy Americorp, Ltd

    440 N Wabash Ave Unit 2907, Chicago, IL 60611
  • /23

    $349,900

    $9K PRICE DROP Pending
    • 3 Beds
    • 2 Baths

    6209 N Mozart St Unit 3S, Chicago, IL 60659

    Vintage charm meets contemporary style in this sunny and spacious 3-bedroom, 2-bath top-floor condo on a quiet, tree-lined street. This inviting home features hardwood floors throughout, an extra-wide living room with elegant coved ceilings with a decorative fireplace, and a separate dining room with ample space for a full-sized dining set. Enjoy the best of both worlds with cozy radiator heat

    Tara Leinenweber Redfin Corporation

    6209 N Mozart St Unit 3S, Chicago, IL 60659
  • /29

    $415,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    1311 W Fillmore St Unit A, Chicago, IL 60607

    Welcome home to this beautifully updated 2 bed, 2 bath condo tucked away on a quiet tree-lined street in the heart of Little Italy/University Village. This spacious home offers an ideal open-concept layout with hardwood floors throughout, great natural light, and a cozy wood-burning fireplace anchoring the living and dining space. The updated kitchen features quartz countertops, ample cabinet

    Almir Bajric Real Broker LLC

    1311 W Fillmore St Unit A, Chicago, IL 60607
  • /21

    $340,000

    Pending
    • 2 Beds
    • 2 Baths

    6139 N Paulina St Unit 1, Chicago, IL 60660

    Welcome home to this beautiful 2-bedroom, 2-bath condominium in the heart of Edgewater! This spacious home blends vintage charm with modern finishes, featuring an open-concept living and dining area filled with natural light, hardwood floors throughout, and a thoughtfully designed layout perfect for both everyday living and entertaining. The kitchen offers ample cabinet space, stainless steel

    Jason Marsing Fulton Grace Realty

    6139 N Paulina St Unit 1, Chicago, IL 60660
  • /16

    $495,000

    Pending
    • 3 Beds
    • 1 Bath

    3551 N Reta Ave Unit 2, Chicago, IL 60657

    Charming 3-bedroom, 1-bath second-floor unit in an intimate three unit building on a picturesque tree-lined street just blocks from Wrigley Field. Filled with original character and charm, this home features high ceilings, hardwood floors throughout, and abundant natural light. The bright living room showcases a wood burning fireplace and three large windows and flows through an arched doorway

    Layching Quek Redfin Corporation

    3551 N Reta Ave Unit 2, Chicago, IL 60657
  • /26

    $349,995

    Pending
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    525 W Hawthorne Place Unit 2004, Chicago, IL 60657

    Rarely Available 20th-Floor 2-Bedroom, 2-Bath Residence at Hawthorne Place with Sweeping Lake Michigan & Wrigley Field Views! Experience luxury living in one of Lakeview East's premier full-service buildings, Hawthorne Place. This rarely available and highly sought-after floor plan offers approximately 1,200 square feet of beautifully designed living space with two generously sized bedrooms, two

    Matt Laricy Americorp, Ltd

    525 W Hawthorne Place Unit 2004, Chicago, IL 60657
  • /29

    $475,000

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    201 N Westshore Dr Unit 604, Chicago, IL 60601

    Experience sophisticated city living in this spacious 2 bedroom, 1.5 bath condo at The Lancaster! Floor-to-ceiling windows fill the home with natural light, while the open-concept living and dining area flows seamlessly into the kitchen, featuring granite countertops, stainless steel appliances, a breakfast bar, and pantry. A desirable split-bedroom floor plan provides added privacy. The generous

    Layching Quek Redfin Corporation

    201 N Westshore Dr Unit 604, Chicago, IL 60601
  • /31

    $330,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,042 Sq Ft

    3827 W Hayford St, Chicago, IL 60652

    Charming one-story single-family home with 3 bedrooms and 1 bathroom, recently remodeled and move-in ready. Hardwood floors run throughout the bedrooms, and ceramic tile flows through the living room and kitchen. Enjoy cozy evenings by the electric fireplace, plus the comfort of central heating and cooling. Outside, you'll find a 2-car detached garage, a convenient patio, and a fenced yard, great

    Rosa Flores Redfin Corporation

    3827 W Hayford St, Chicago, IL 60652
  • /23

    $369,900

    Pending
    • 4 Beds
    • 3 Baths
    • 2,281 Sq Ft

    5718 W Superior St, Chicago, IL 60644

    Step into comfort and style in this thoughtfully remodeled home in the heart of Chicago's Austin neighborhood! This timeless Cape Cod is perfectly designed for modern living with timeless charm, situated on an expansive 1.5 city lots. A welcoming front porch leads into the bright, open living and dining spaces featuring rich hardwood floors and a classic gas fireplace, creating the ideal setting

    Melissa Kingsbury Redfin Corporation

    5718 W Superior St, Chicago, IL 60644
  • /16

    $265,000

    • 2 Beds
    • 1 Bath
    • 906 Sq Ft

    4250 N Marine Dr Unit 2130, Chicago, IL 60613

    Two bedrooms. Lake view. Endless possibilities. Perched on the 21st floor of sought-after, investor friendly Imperial Towers, this bright and move-in-ready home offers something buyers rarely find at this price point: the flexibility of a two-bedroom floor plan without sacrificing light, views, or location. Whether you need a dedicated home office, guest room, creative space, or simply room to

    Wanda Austin-Wingood Redfin Corporation

    4250 N Marine Dr Unit 2130, Chicago, IL 60613
  • /27

    $365,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,463 Sq Ft

    5406 S East View Park Unit 3, Chicago, IL 60615

    Beautiful top-floor 2-Bed/2-Bth condo with tons of vintage charm in East View Park! This light-filled home features expansive windows and a sunroom off the living area. The spacious living room showcases a cozy fireplace and gleaming hardwood floors that extend throughout the unit. The formal dining room is truly a standout, complete with rich wood-paneled walls, beamed ceilings, and an original

    Cesar Juarez Redfin Corporation

    5406 S East View Park Unit 3, Chicago, IL 60615
  • /19

    $365,000

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    6007 N Sheridan Rd Unit 29F, Chicago, IL 60660

    Set in Malibu, a full-amenity lakefront building in Edgewater, this home offers unbeatable access to beaches, bike paths, parks, dining, and transit, including the CTA Red line and express buses. Steps from various grocery stores, including Mariano's and Whole Foods. Tastefully remodeled unit with expansive windows and 2 balconies flood the place with light. Full amenity building with 24/7

    Kate Seemann Redfin Corporation

    6007 N Sheridan Rd Unit 29F, Chicago, IL 60660
  • /38

    $265,000

    • 4 Beds
    • 2 Baths

    9913 S Parnell Ave, Chicago, IL 60628

    Welcome to 9913 S. Parnell! This spacious 4-bedroom, 2-bath home offers a functional layout with plenty of flexibility. The open kitchen creates a welcoming gathering space. The home offers a three-season room on the main level, ideal for a home office, playroom, or additional living space, and a finished basement including a dedicated office/den area. Recent improvements completed in June 2026

    Jean Walker Redfin Corporation

    9913 S Parnell Ave, Chicago, IL 60628
  • /30

    $438,000

    • 2 Beds
    • 2 Baths
    • 1,273 Sq Ft

    1515 S Prairie Ave Unit 506, Chicago, IL 60605

    Welcome to this beautiful southeast-facing corner residence in the highly sought-after Prairie House, perfectly situated in Chicago's desirable South Loop. This bright and spacious 2-bedroom, 2-bath condo offers 1,273 square feet of comfortable living space with spectacular views of Lake Michigan, Soldier Field, and the Museum Campus from your private outdoor balcony. The open-concept living and

    Jennifer Stokes Habetler Redfin Corporation

    1515 S Prairie Ave Unit 506, Chicago, IL 60605
  • /55

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,409 Sq Ft

    260 E Chestnut St Unit 2904, Chicago, IL 60611

    LUXURY LAKEFRONT LIVING IN THE HEART OF STREETERVILLE Experience an extraordinary lifestyle from this rarely available high-floor residence, perfectly positioned just steps from Lake Michigan and the world-renowned Magnificent Mile. Nestled high above the city on the 29th floor, this impressive 2-bedroom, 2-bathroom home offers nearly 1,409 square feet of thoughtfully designed living space and

    Slawomir Rachmaciej Exit Realty Redefined

    260 E Chestnut St Unit 2904, Chicago, IL 60611
  • /17

    $374,900

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    1249 W Roscoe St Unit 1, Chicago, IL 60657

    Welcome to 1249 W. Roscoe- located on a beautiful tree lined street just steps to Southport Corridor! This 2-bedroom home combines the perfect mix of vintage charm and modern updates, offering everything you need for comfortable city living. Inside, you'll find beautiful Brazilian cherry hardwood floors throughout, and exposed brick. The open-concept kitchen features a custom subway tile

    Kathryn Schrage Redfin Corporation

    1249 W Roscoe St Unit 1, Chicago, IL 60657
  • /10

    $274,900

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    260 E Chestnut St Unit 2505, Chicago, IL 60611

    Move right into this beautifully maintained one bedroom in an unbeatable location. This home offers a clean, functional layout with great natural light and a comfortable living space that's easy to make your own. Truly move in ready, making it a perfect option for a primary residence, in town, or investment. Located just steps from everything Streeterville has to offer, you're surrounded by top

    Jacob Reiner Redfin Corporation

    260 E Chestnut St Unit 2505, Chicago, IL 60611
  • /23

    $247,500

    • 1 Bed
    • 1 Bath
    • 849 Sq Ft

    440 N Wabash Ave Unit 3204, Chicago, IL 60611

    Bright and sunny 1 bedroom, 1 bath corner unit with stunning city views in a prime River North location! This spacious unit features new carpet throughout and an open concept living and dining area with two walls of windows that flows into the kitchen with a breakfast bar that opens to the living area. The bedroom is generously sized to accommodate a queen or king bed and offers two closets

    Jacqueline Colando Redfin Corporation

    440 N Wabash Ave Unit 3204, Chicago, IL 60611
  • /27

    $324,900

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    811 S Lytle St Unit 110, Chicago, IL 60607

    Welcome to 811 S Lytle St, Unit 110-a loft-style 2-bedroom, 1.5-bath condo in Little Italy with a private double balcony providing delightful park views. The home offers a functional open layout ideal for everyday living and entertaining. Both bedrooms provide flexible options for sleeping, guests, or a home office, and in-unit laundry adds day-to-day convenience. Freshly painted and move-in

    Camie Cirrincione Redfin Corporation

    811 S Lytle St Unit 110, Chicago, IL 60607
  • /36

    $435,000

    Pending
    • 5 Beds
    • 4 Baths

    5011 S Kilbourn Ave, Chicago, IL 60632

    Exceptional investment opportunity in the heart of Chicago! This well-maintained all-brick three-unit building offers an ideal combination of owner-occupant potential and strong rental income. Rehabilitated in 2024, the property features three spacious units with a total of five bedrooms and four full bathrooms, providing versatile living arrangements for a variety of buyers. The recently

    Kimberly Brown-Lewis Redfin Corporation

    5011 S Kilbourn Ave, Chicago, IL 60632
  • /33

    $425,000

    Pending
    • 2 Beds
    • 2.5 Baths

    4930 S Cornell Ave Unit E, Chicago, IL 60615

    Very rarely available two bedroom townhome in the heart of Hyde Park. Freshly painted and completely move in ready, this home offers the space and privacy of a single family home with the convenience of low maintenance living. The bright main level features hardwood floors, soaring ceilings, oversized windows, a fireplace, and an open living and dining space overlooking the beautifully landscaped

    Jacob Reiner Redfin Corporation

    4930 S Cornell Ave Unit E, Chicago, IL 60615
  • /76

    $345,000

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths

    4925 S Justine St, Chicago, IL 60609

    Excellent opportunity to own this newly remodeled, turnkey frame 2-unit property located in the heart of Back of the Yards! Perfect for an investor looking for strong rental income or an owner-occupant looking to live in one unit and rent out the other. This property has undergone a recent rehab and features brand-new kitchen cabinets boasting modern finishes, completely updated contemporary

    Angelica Pasten Century 21 Hallmark Ltd.

    4925 S Justine St, Chicago, IL 60609
  • /25

    $349,995

    • 1 Bed
    • 1.5 Baths
    • 955 Sq Ft

    435 W Erie St Unit 1506, Chicago, IL 60654

    Stunning River North Condo with Sweeping City Views in Erie Center Tower! Welcome home to this spacious and sun-filled 1-bedroom, 1.1-bath residence in the highly sought-after Erie Center Tower. This beautifully maintained home features an open-concept floor plan designed for today's lifestyle, with a generous living room, cozy fireplace, and floor-to-ceiling windows that flood the space with

    Matt Laricy Americorp, Ltd

    435 W Erie St Unit 1506, Chicago, IL 60654
  • /23

    $475,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,342 Sq Ft

    6209 N Caldwell Ave, Chicago, IL 60646

    Charming 2-Bed/1.5-Bth classic ranch in the highly sought-after Edgebrook neighborhood, offering the perfect blend of suburban tranquility within Chicago city limits. This home boasts fantastic curb appeal with mature landscaping and large windows that fill the space with natural light. Step inside to a bright and inviting living room featuring hardwood floors that extend throughout much of the

    Niki Syllantavos Redfin Corporation

    6209 N Caldwell Ave, Chicago, IL 60646
  • /23

    $220,000

    Pending
    • 4 Beds
    • 3 Baths
    • 1,798 Sq Ft

    8810 S Racine Ave, Chicago, IL 60620

    Welcome to this inviting bungalow in the heart of Chicago's Auburn Gresham neighborhood. The charming front porch leads into a space filled with character, including original hardwood flooring and arched doorways. The spacious living room is filled with natural light from the large bank of windows, while the formal dining room with chair rail details is perfect for hosting meals. The updated

    Melissa Kingsbury Redfin Corporation

    8810 S Racine Ave, Chicago, IL 60620
  • /34

    $435,000

    $35K PRICE DROP Pending
    • 3 Beds
    • 1.5 Baths
    • 1,573 Sq Ft

    5704 N Major Ave, Chicago, IL 60646

    Welcome to this classic brick English Tudor home, perfectly situated on a peaceful, tree-lined street. Combining timeless character with thoughtful updates, this home offers comfortable living spaces both inside and out. The main level features two spacious bedrooms and a beautifully renovated full bathroom with a modern walk-in shower. Enjoy entertaining in the separate formal dining room, while

    Niki Syllantavos Redfin Corporation

    5704 N Major Ave, Chicago, IL 60646
  • /19

    $425,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,102 Sq Ft

    2045 W Concord Place Unit 307, Chicago, IL 60647

    OPEN 8/16 CANCELLED -Live in the center of Wicker Park in this bright and spacious 2-bedroom, 1.5-bath condo offering an open floor plan, private outdoor space, and an unbeatable location just off Milwaukee Avenue. Southwest-facing exposures fill the home with natural light, while the generous living and dining area provides plenty of space to entertain, relax by the fireplace, or step outside to

    Matt Laricy Americorp, Ltd

    2045 W Concord Place Unit 307, Chicago, IL 60647
  • /26

    $389,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    701 S Wells St Unit 2005, Chicago, IL 60607

    Stunning Printer's Row 2B/2B with breathtaking city views and a highly sought-after split floor plan. This bright, open-concept home is designed for both comfortable living and effortless entertaining, featuring expansive living and dining space, hardwood floors, fireplace, and floor-to-ceiling windows that flood the unit with natural light. The updated kitchen boasts granite countertops, a large

    Vishakha Patel Compass

    701 S Wells St Unit 2005, Chicago, IL 60607
  • /26

    $395,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,976 Sq Ft

    2636 N Neva Ave, Chicago, IL 60707

    Welcome to this clean, well-maintained brick bungalow situated on a 30' lot in the beautiful Montclare neighborhood. The main floor features a spacious living room highlighted by a lovely bay window, a formal dining room, two comfortable bedrooms with classic hardwood flooring, a full bathroom, and an inviting eat-in kitchen. Other amenities include an enclosed front porch and an expansive deck

    Nancy Huetteman Redfin Corporation

    2636 N Neva Ave, Chicago, IL 60707
  • /21

    $375,000

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    2343 N Greenview Ave Unit 105, Chicago, IL 60614

    Rarely available and perfectly located in the heart of Lincoln Park/DePaul! Move right into this gorgeous 2-bedroom, 1,100-square-foot duplex-down condo offering an open, spacious layout and numerous recent updates. The main level features refinished hardwood floors, a wood-burning fireplace, ample dining space, and an updated kitchen with 42-inch cabinetry, stainless steel appliances, quartz

    Matt Laricy Americorp, Ltd

    2343 N Greenview Ave Unit 105, Chicago, IL 60614
  • /47

    $389,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    33 W Delaware Place Unit 13A, Chicago, IL 60610

    Stunning, Newly Renovated Gold Coast Condo - Perfect for Investors and Homeowners! Rarely available two-bedroom, two-bathroom corner residence in the heart of the Gold Coast, offering breathtaking southeast views of Chicago's iconic skyline. This bright and spacious home has been thoughtfully renovated and is move-in ready, featuring newly refinished hardwood floors stained in a sophisticated

    Patrick O'Dwyer Compass

    33 W Delaware Place Unit 13A, Chicago, IL 60610

Showing Results 281 - 320, Page 8 of 18

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