South Deering Homes for Sale

Welcome to South Deering, a hidden gem nestled on the far southeast side of Chicago, Illinois. This vibrant neighborhood is a harmonious blend of rich history and modern living, making it an ideal place for families and individuals seeking a welcoming community. With its roots tracing back to the early 20th century, South Deering boasts a unique character that reflects its industrial past while embracing the future.

One of the standout features of South Deering is its stunning residential charm. The neighborhood is primarily composed of single-family homes, many of which showcase classic brick facades and spacious yards, perfect for outdoor gatherings and family activities. The tree-lined streets create a picturesque backdrop, inviting residents to take leisurely strolls and enjoy the community’s serene atmosphere.

For those looking to make South Deering their home, there are a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re in search of a cozy starter home or a larger property for a growing family, the real estate options here are plentiful. The affordability of homes in South Deering makes it an attractive choice for first-time buyers and seasoned investors alike.

In addition to its residential appeal, South Deering offers convenient access to parks, schools, and local amenities, ensuring that everything you need is just a stone’s throw away. The community spirit is palpable, with friendly neighbors and local events that foster connections.

Explore the charm of South Deering today, and discover why so many are proud to call this neighborhood home. Your perfect home awaits!

Newest South Deering Homes for Sale

$249,900

3 Beds ⋅ 2 Baths ⋅ 12713244 MLS ⋅ ACTIVE Status

GREAT SPLIT-LEVEL SINGLE-FAMILY HOME WITH 3 BEDROOMS, 1 FULL BATH, AND 1 HALF BATH, LOCATED IN A GREAT NEIGHBORHOOD! MANY RECENT UPDATES INCLUDE A NEW KITCHEN WITH QUARTZ COUNTERTOPS, UPDATED BATHROOMS, REFINISHED HARDWOOD FLOORS, ALL-NEW LIGHT FIXTURES, NEW VINYL TILE FLOORING IN THE LOWER LEVEL, NEW RECESSED LIGHTING IN THE LIVING ROOM, AND NEW WINDOWS ON THE SECOND FLOOR. THE MAIN LEVEL FEATURES A SUNNY, SPACIOUS LIVING ROOM AND DINING ROOM WITH RECESSED LIGHTING, PLUS A NICE KITCHEN WITH AN EAT-IN BREAKFAST SPACE. THE UPPER LEVEL OFFERS 3 SPACIOUS BEDROOMS AND A FULL BATH. THE LOWER LEVEL INCLUDES A LARGE FAMILY ROOM, HALF BATH, LAUNDRY ROOM, AND UTILITY ROOM. LARGE STORAGE IN THE CRAWL BASEMENT. ENJOY A 2-CAR GARAGE WITH A PARTY DOOR, A LARGE YARD, AND A PATIO-PERFECT FOR ENTERTAINING. CONVENIENT LOCATION! A NICE HOME IN A NICE NEIGHBORHOOD. PRE-APPROVED BUYERS-DON'T MISS THIS OPPORTUNITY! SHOW AND SELL NOW!!!

10508 S Bensley Avenue, Chicago

$299,900

3 Beds ⋅ 2 Baths ⋅ 12712250 MLS ⋅ ACTIVE Status

WELCOME TO THIS BEAUTIFULLY UPDATED HOME OFFERING 3 BEDROOMS AND 1 BATH ON THE MAIN LEVEL, PLUS A NICELY FINISHED BASEMENT WITH AN ADDITIONAL BEDROOM AND FULL BATHROOM. THE HOME FEATURES MODERN UPDATES THROUGHOUT WHILE MAINTAINING A WARM, INVITING FEEL. THE EXTRA SPACE DOWNSTAIRS IS PERFECT FOR GUESTS, A PRIVATE RETREAT, OR FLEXIBLE LIVING. New AC to be installed! A TRUE MOVE IN READY GEM!

9824 S Escanaba Avenue, Chicago

$259,000

4 Beds ⋅ 2 Baths ⋅ 12711921 MLS ⋅ ACTIVE Status

10426 S Calhoun Avenue, Chicago

$195,000

2 Beds ⋅ 1 Baths ⋅ 12707381 MLS ⋅ PRICE CHANGE Status

Welcome home to this beautifully updated brick raised ranch on a quiet tree lined street in the heart of South Deering! Step inside to a bright and inviting living room featuring hardwood floors. The remodeled kitchen is designed for both style and function, and chic shaker cabinetry perfect for everyday meals and entertaining. The main level offers two generously sized bedrooms and a tastefully updated full bathroom. Downstairs, the basement provides exceptional storage space, a third bedroom, a dedicated laundry area, and endless possibilities for future expansion, recreation space, or a home gym. Enjoy outdoor living in the private, fully fenced backyard, ideal for gatherings, pets, and gardening. A detached two-car garage provides convenient parking and additional storage. Located in Chicago's South Deering neighborhood, this home offers easy access to shopping, dining, schools, public transportation, and major expressways. Nearby attractions include Trumbull Park with its recreation center, sports fields, and fitness facilities, as well as Big Marsh Park, a popular destination for biking, walking trails, nature enthusiasts, and outdoor recreation. Don't miss this move-in ready opportunity to own a charming, updated home with room to grow in a convenient South Side location. Schedule your private showing today!

10145 S Bensley Avenue, Chicago

$222,999

3 Beds ⋅ 2 Baths ⋅ 12705190 MLS ⋅ ACTIVE Status

Beautifully rehabbed 3bedroom, 2bath home in a quiet Chicago neighborhood, featuring a bright open concept layout and refinished hardwood floors throughout. The interior showcases a modern black and white design theme with brand new white cabinets, quartz countertops, stainless steel appliances, a new modern white backsplash, modern black ceiling fans, and sleek black hardware for a clean, contemporary feel. The home is equipped with a full forced-air HVAC system with central AC-no radiators, providing efficient heating and cooling year round. Both bathrooms have been fully updated with white tile, new modern vanities, and stylish black fixtures, creating a fresh, spa like look. The home sits on a fully gated lot and includes an extremely well maintained 2 car garage with a spacious concrete parking pad in front-perfect for extra parking or hosting family and friends outdoors. The backyard is very spacious, offering plenty of room for gatherings, gardening, or creating your own outdoor oasis. Enjoy a quick drive to downtown Chicago and the convenience of being able to reach Indiana quickly, plus easy access to major highways for a smooth commute. The library is just one block away, and parks are nearby. This move in ready home is truly a must see-don't miss this gem!

10055 S Oglesby Avenue, Chicago

$260,000

5 Beds ⋅ 2 Baths ⋅ 12664904 MLS ⋅ PRICE CHANGE Status

6-bedroom, 1.5-bath brick home in the South Deering/Trumbull Park area! Features hardwood, ceramic, and laminate flooring, remodeled bathrooms, stainless steel refrigerator and stove, and quartz kitchen countertops. Master bedroom bath. The main level offers 3 bedrooms, with 2 dormer-style bedrooms on the upper level and 1 large bedroom in the basement. Shingle roof, and circuit breakers. Basement includes both interior and exterior access. Garage with awning. Oversized Chicago Lot. Fast access to I-90/I-94. Close to Marian R. Byrnes Natural Area and Trumbull/Lyman Park.

10134 S Bensley Avenue, Chicago

$269,900

3 Beds ⋅ 2 Baths ⋅ 12638438 MLS ⋅ ACTIVE Status

Step into worry-free living with this beautifully renovated home, complete with a home warranty. This impressive all brick home features 3 spacious bedrooms and 1 full bath on the second level, plus an additional half bath in the finished basement for added convenience. The updated kitchen shines with new appliances, modern finishes, and stylish cabinetry, making it perfect for everyday living and entertaining. Designed for connection and everyday living, the spacious dining room flows seamlessly off the kitchen and features a charming pass-through view window that is perfect for entertaining, staying connected with guests, and creating an open, and inviting feel. Enjoy elegant hardwood flooring, recessed can lighting, and beautiful light fixtures throughout that add warmth and sophistication to every room. The finished basement offers additional living space ideal for a family room, recreation area, home office, or guest space. This move-in-ready gem combines comfort, style, and functionality This is a must-see for buyers seeking modern updates and extra living space! BOOK YOUR SHOWINGS NOW!

10118 S Luella 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.