We analyze thousands of real estate agents in Chicago’s South Side neighborhood and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for August 2026.*
69 recent sales
$35K-$515K price range
$260K median price
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
Information and statistics on the latest trends in the South Side real estate market. *
Apr 1, 2026 - Jun 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Apr 2026 - Jun 2026).
South Side’s rolling three-month data through June 2026 shows home values climbing meaningfully from a year ago, with the typical home value up about 14 percent while Chicago overall is growing more slowly. Compared with the citywide median sale price, South Side homes are still more affordable, even as local prices trend higher.
In the latest period, buyers are seeing more options, with active listings slightly above last year and around 1,545 homes on the market. Conditions are still tilted toward sellers though, as months of supply sits at 5.2 locally versus just 2.8 across Chicago, and roughly a quarter of homes sell above list price.
Momentum has picked up this spring, with homes sold and pending sales both higher than three months ago and typical days on market dropping from 91 to 76. With about one-third of listings going off the market within two weeks and the average sale-to-list ratio near 98 percent, well-priced homes are moving efficiently. Buyers and sellers who want to navigate these shifting trends in South Side can turn to Agent Pronto to connect with a knowledgeable local agent.
South Side offers residents a vibrant, neighborly mix of culture, community, and opportunity, with accessible services, local businesses, parks, and a resilient, inclusive spirit that keeps neighbors connected.
South Side in Chicago covers a wide area of neighborhoods with quick access to downtown via the Red and Green Lines and major routes like Lake Shore Drive and the Dan Ryan Expressway. From historic streets in Bronzeville to waterfront trails in South Shore, residents find a mix of long‑time community roots and everyday convenience that works for commuters, students, and families alike.
Outdoor access is a major draw. The lakefront at Promontory Point and Oakwood/41st Street Beach offers paths for biking and jogging along Lake Michigan. Large parks, including Jackson Park and Washington Park, give South Side residents access to playgrounds, athletic fields, and cultural events.
Everyday needs are close at hand. Neighborhood commercial corridors feature local staples like Original Jimmy’s Red Hots and cafes, barbershops, and small grocers, while larger shopping areas in nearby Loop and Near North Side are a short drive or train ride away. Cultural landmarks such as the DuSable Black History Museum and Education Center and the Museum of Science and Industry sit near residential streets, creating a rare blend of quiet blocks and major attractions.
Housing ranges from classic brick two‑flats and bungalows to updated condos and newer construction. Because each pocket of South Side has its own character and price point, working with a local expert helps clarify where transit options, schools, and amenities best match your goals. Agent Pronto connects buyers and sellers with trusted South Side agents so your move feels more informed and less stressful.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“I've worked with Shawn Jones for nearly 10 years. He helped me find my first apartment, and first home after getting married. He is a deeply considerate, caring, and experienced agent. I can't recommend him highly enough.”
“Rose Riodan, did excellently well, always available for phone calls, chat and prompt with emails. Gave great advice and recommendations that supported making informed decisions.”
“We had an amazing experience working with Andrew at Century 21 Circle! From the very beginning, Andrew was incredibly knowledgeable, patient, responsive, and always willing to go above and beyond for us. He was quick to respond to every question and did everything he could to get us into showings, even when we needed to move quickly or work around our schedules. Buying a home can be stressful, but Andrew made the process feel so much easier. We always felt like he had our best interests in mind and genuinely wanted to help us find the right home. We couldn’t have asked for a better realtor and are so grateful for everything he did to help us find our home! If you’re looking for a realtor, we highly recommend Andrew and the team at Century 21 Circle!”
“Kim was easy to work with. She explained everything very clearly, which was something important to me as a first time seller. Her attention to detail and open communication were greatly appreciated and I highly recommend working with her.”
“Emir is a wonderful agent! His expertise in real estate was great and he was extremely helpful with any questions. He was patient and always responded in a timely manner. I would highly recommend hiring Emir as your agent!”
“We've known Brittany for many years and we have had experience working with her in the past. We chose to work with her once more because of our wonderful experience In the past. I would highly recommend her because of her professional approach and her genuine interest to provide the best to her customers.”
“Paula was fantastic! She was knowledgeable, very responsive, and was able to walk me through the process step-by-step as a first-time seller. Would highly recommend to anyone and everyone!”
“I previously used Jeffry Phillips to sell a house I inherited. It was a very emotional time and he was fantastic. He was very knowledgeable and gave suggestions of things that could be done to the house prior to selling it. Because that experience was so positive and he was so professional I utilized his services when it was time for me to sell my house. When it came time to sell my home, he was professional and extremely knowledgeable about the Garfield Ridge neighborhood. I would highly recommend him to any of my friends family, and neighbors if they are buying or selling a house.”
“Katherine Rubis was very patient with me during the year that I was looking for homes. She was always available to discuss our next steps or to show me new listings. Every single part of the process that Katherine handled was very smooth and easy for me. She is an outstanding agent and I will definitely call her when I am in the market to sell or buy a home again. There is nothing else she could have done to make me more satisfied with working with her. I have zero complaints.”
“Vicky knows real estate and has excellent communication skills. She relayed her recommendations and expectations. Her experience expedited the sale of my home. I had a contract in less than two days. She is a hard worker and always available to respond to questions or concerns. I highly recommend her for an agent.”
“Melissa Young is an excellent realtor. I highly recommend her.”
“Laura is Amazing!”
“Working with Tracy to buy our home was a great experience and she was always available and communicative even as we navigated some difficult parts of the negotiation with the seller. She was personally at every visit and even at the inspection and closing, going way above and beyond my expectations and previous experiences with buying agents. Thanks to her we found a home for our family and while we don't plan to buy in the near future I'd be happy to work with her again and again. Thanks Tracy!”
“Steven was very helpful, knowledgeable, passionate, and most importantly he met all of my needs! I will definitely use him for all of my future home purchases in the near future. Thanks again Steven, he's definitely a ROCK STAR! I can't wait to work with him in the near future. Betty Ng”
“Meldina is an expert in the local market and an exceptional negotiator. Her professionalism, communication, and dedication exceeded our expectations. We highly recommend her!”
“Barb was 1/20 realtors who was willing to work with me in the beginning over 9 years ago. This is when I first purchased my home. I was cheap buyer. It went without saying I was going to be using her for the sale of the home 9 years later. She handled the hurdles flawlessly and talked me through and coached me the entire way. To say I appreciate her is an understatement. I sold my home after we relocated it of state and she coordinated every logistic of that sale on my behalf to he best of her ability. I recommend her without fail and would point every person in her direction that has a need for a solid realtor.”
“It was a joy to work with Kathryn she was able to answer every question I had, her knowledge goes a long way and I will definitely recommend her to friends and family.”
“Working with Kolby Banks was an exceptional experience. His professionalism, deep market knowledge, and proactive communication turned a complex process into a seamless one. Kolby is a sharp negotiator who truly advocates for his clients' best interests. If you want a realtor who is transparent, detail-oriented, and results-driven, we highly recommend Kolby Banks. He’s simply the best in the business!”
“Our house could be considered high end property in the neighborhood. Cinny worked hard to get it under the contract in a week and sold our house a little over a month. We are happy about the result. During the process, there were ups and downs which made us nervious. Cinny listened to our concerns and gave us professional advice.”
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”
There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around South Side. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your South Side Realtor® or real estate agent today.
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