Douglas Homes under $500,000

Welcome to Douglas, a vibrant neighborhood nestled in the heart of Chicago, Illinois. Known for its rich history and diverse community, Douglas offers a unique blend of urban living and suburban charm. As you stroll through the tree-lined streets, you'll discover a mix of architectural styles, from classic brick bungalows to modern condominiums, making it an attractive destination for homebuyers seeking character and affordability.

One of the standout features of Douglas is its accessibility to public transportation and major highways, making commutes to downtown Chicago a breeze. The neighborhood is also home to several parks, including the beautiful Douglas Park, which boasts sports facilities, walking trails, and lush green spaces perfect for picnics and relaxation. The community is vibrant, with local shops, cafes, and restaurants that reflect the rich cultural tapestry of the area.

For those looking for homes under $500,000, Douglas is an ideal choice. The real estate market here offers a variety of options, catering to first-time buyers, families, and investors alike. You can find spacious single-family homes and cozy condos, all within a budget that allows for comfortable living without sacrificing quality.

With its welcoming atmosphere, strong sense of community, and affordable housing options, Douglas is not just a place to live—it's a place to thrive. Whether you're looking to plant roots or invest in a promising neighborhood, Douglas invites you to explore all that it has to offer. Come discover your dream home in this charming Chicago enclave!

Newest Douglas Homes under $500,000

$150,000

1 Beds ⋅ 1 Baths ⋅ 12773683 MLS ⋅ NEW Status

Spacious 1 bedroom condo, filled with natural light and lake views. Move in ready! Beautiful South/East views, located on the top floor. Walking distance to Lake Michigan. Close to Hospital, llT, McCormick Place Convention Center, MotorRow restaurants and shops and centrally located next to I-55 , 90, and 290. Elevator building. PARKING permit is available within the condo community. Great for owner or investor. RENTALS ALLOWED.

345 E Eastgate Place Unit #604, Chicago

$469,000

3 Beds ⋅ 3 Baths ⋅ 12762308 MLS ⋅ ACTIVE Status

Fresh opportunity in the heart of Bronzeville! Step into this spacious 3-bedroom, 2.5-bath, single-level penthouse condo that offers the perfect blend of comfort, style and an unbeatable Chicago location just minutes from downtown Chicago, Lake Michigan, The Illinois Institute of Technology, Guaranteed Rate Field and major expressways. Thoughtfully updated in 2024. The home features re-finished hardwood floors, beautiful new cabinetry, quartz countertops, stainless steel appliances and updated lighting throughout. The open kitchen and living room create a fantastic living space, including a huge kitchen island that is the center for cooking and entertaining. The Main living space is complemented by two private rooftop patio desks off the kitchen and living room, each with views of the neighborhood and downtown Chicago, perfect for enjoying your morning coffee, tending to a container garden, or taking in the sunset. The spacious primary suite offers a walk-in closet, private balcony, and a luxurious en-suite bath with a jetted soaking tub and separate rainfall shower. Each bedroom offers ample space for a king size bed and full bedroom set, in addition to a second walk-in closet and private balcony on the secondary bedroom. The home also features in-unit washer and dryer, a new furnace that was installed in January 2026, providing reliable heating and air conditioning. Adding to that peace of mind, the unit also comes with a covered garage parking space that is included at no additional monthly cost.

3541 S Prairie Avenue Unit #4, Chicago

$250,000

6 Beds ⋅ 2 Baths ⋅ 12759576 MLS ⋅ ACTIVE Status

3549 S Indiana Avenue, Chicago

$225,000

2 Beds ⋅ 1 Baths ⋅ 12749724 MLS ⋅ ACTIVE Status

Welcome to this well-maintained 2-bedroom, 1-bath condo offering comfortable city living in a convenient South Loop/Bronzeville location. This spacious and affordable home features large windows that provide abundant natural light, generous in-unit storage, fresh paint, and new laminate flooring throughout. An exterior parking space and additional storage are also included. Enjoy easy access to public transportation, shopping, dining, parks, and everyday conveniences, all just minutes from your door. A great opportunity for buyers looking for value, space, and accessibility in the city. Monthly assessments include Cambridge Condo Association at $572 and Eastgate Village HOA at $94.42.

345 E Eastgate Place Unit #302, Chicago

$335,000

2 Beds ⋅ 2 Baths ⋅ 12736225 MLS ⋅ ACTIVE Status

Beautifully-updated and move-in ready 1,500 sq ft, 2 bed/2 bath + den/office space condo, featuring hardwood floors throughout, an open-concept layout, and tons of natural light. Modern kitchen with granite countertops, stainless steel appliances, abundance of cabinetry, and breakfast bar seating. Both brand-new, fully-updated bathrooms showcase contemporary finishes. The oversized primary suite includes a walk-in closet and a luxurious en suite bath with dual vanity, soaking tub, and separate shower. The unit also includes bonus office space, 5 closets for excellent storage, 2 private patios, in-unit washer/dryer, and 1 designated garage parking space in a shared secure area. This prime location provides easy access to highways, public transit, Lake Shore Drive, restaurants, shopping, and parks - everything the South Loop lifestyle has to offer.

31 E 26Th Street Unit #3, Chicago

$335,000

3 Beds ⋅ 2 Baths ⋅ 12736911 MLS ⋅ ACTIVE Status

Step inside this beautifully maintained and luxurious 3-bedroom, 2-bathroom condo you'll appreciate the warm and inviting atmosphere, abundant natural light and the beautiful hard wood floors that flow throughout the home. The spacious open-concept living and kitchen area is perfect for both everyday living and entertaining, featuring custom made window shutters, a cozy gas fireplace and a granite breakfast bar. The kitchen offers stainless steel appliances and custom cabinetry with plenty of storage. All three bedrooms are generously sized with ample closet space, including one bedroom featuring beautiful windowed French doors. The spacious primary suite is a true retreat, with sliding doors leading to a private rear balcony. The ensuite bathroom features a relaxing whirlpool tub, separate walk-in shower, and dual-sink vanity. Additional features include in-unit laundry with a newer stackable washer and dryer, dedicated storage on the ground level, and an assigned parking space in the building's back lot. The unit is also rentable, making this an excellent opportunity for both homeowners and investors. LOCATION, LOCATION, LOCATION! Enjoy easy access to multiple public transportation options and near major expressways, with Downtown Chicago and Chinatown just minutes away. The property is also within walking distance of several colleges including the Illinois Institute of Technology (IIT) and close to Chicago's beautiful lakefront and beaches. Enjoy the convenience of nearby grocery stores, restaurants, shopping, highly regarded charter schools, cultural attractions, and the iconic Chicago White Sox Stadium. With easy access to everything the city has to offer, this is an incredible opportunity to own a home in one of Chicago's most exciting and rapidly evolving neighborhoods. Don't wait-schedule your showing today and make this exceptional condo yours!

3745 S Michigan Avenue Unit #2, Chicago

$309,900

6 Beds ⋅ 4 Baths ⋅ 12674388 MLS ⋅ ACTIVE Status

Attention investors and rehabbers! Spacious brick two-flat built in 2001 featuring two 2-bedroom, 2-bath units plus a finished English basement and detached 2-car garage. Property requires a full renovation. Excellent opportunity to restore and add value in the growing Bronzeville area. Conveniently located near public transportation, major expressways, downtown Chicago, parks, and neighborhood amenities. Property is being sold as-is.

3736 S Calumet Avenue, Chicago

Start Your Search

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.