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Berkshire Hathaway HomeServices Chicago
- Agent Pronto
- Illinois
- Chicago
- Southwest Side
The best way to find top real estate agents in Southwest Side, Chicago, IL
Skip the search. We analyze thousands of real estate agents in Chicago’s Southwest Side neighborhood and nationwide to find you proven local pros, for free.
Compare top Southwest Side real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for May 2026. *
* 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.
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Southwest Side real estate Market Report.
Information and statistics on the latest trends in the Southwest Side real estate market, updated for May 2026. *
Southwest Side is seeing steady activity, with 568 homes on the market and 579 new listings in March 2026. Buyers are keeping pace, as 559 homes went under contract, signaling solid demand. Even with this active flow of listings and contracts, inventory is still down 10.55% from last year, which helps keep conditions tight.
Prices are holding firm in response to this supply and demand balance. The typical home value is about $280,000, well below the broader Chicago figure of $411,050, and is up 1.82% from a year ago. List prices are edging upward, with the median list price at $289,900 in March and projected to reach $290,350 in April 2026.
Homes are spending more time on the market, now a median of 69 days, which is nearly 23% longer than a year ago and up almost 3% just since last month. Even so, this is still a seller’s market, with a strong market gauge reading of 10 and roughly 32.76% of homes selling above list price, supported by an average sale-to-list ratio of 0.98. Whether you are a buyer trying to navigate tighter inventory or a seller aiming to price correctly in these shifting conditions, Agent Pronto can connect you with a local agent who understands the Southwest Side market.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Southwest Side has to offer.
Southwest Side offers residents a strong sense of community, affordable housing, plentiful parks and green spaces, locally owned shops and eateries, family-friendly events, and convenient access to jobs and transit.
Southwest Side offers a distinctly rooted feel compared with trend-focused North Side neighborhoods, drawing many who want long term stability and strong community ties. Spanning areas like Gage Park, Chicago Lawn, and West Lawn, it blends classic brick bungalows with multi generation homes and newer construction. Families value local schools such as Curie High School and Gage Park High School, and the easy access to Midway Airport appeals to frequent travelers and aviation workers.
Daily life leans practical and community focused. Residents gather at Marquette Park for soccer leagues, walking paths, and lake views, while smaller parks dot residential blocks. Casual dining ranges from long standing taquerias along 55th Street to classic Polish and Lithuanian spots closer to Garfield Ridge. The Chicago Transit Authority Orange Line and nearby bus routes keep commutes into downtown manageable, especially for those who split work between home and the Loop.
The housing market here can move quickly, particularly near transit corridors and well regarded schools. Buyers benefit from understanding micro neighborhood differences and upcoming infrastructure projects, and sellers gain an edge by timing listings around seasonal demand and local trends. Whether you are moving within the Southwest Side or arriving from elsewhere in Cook County, Agent Pronto can connect you with a local real estate professional who understands this community and can guide both buyers and sellers from preparation through closing.
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“After a bad experience with another Realtor, Kathy was recommended to me by a friend and I couldn't of been more pleased that I went with the recommendation. Kathy has great attention to detail when it comes to reviewing the home in person and had a very strategic approach in a multiple bid scenario that won my home at a fair market value. She was also extremely responsive at anytime of the day and was always available to answer any questions!!! It was such a relief to have Kathy as my realtor. Truly best in class service!”
Berkshire Hathaway Chicago
“Kim was outstanding throughout both the sale of our home and the purchase of our new one. Her expertise and guidance were instrumental in making the entire process smooth and stress-free. She brings a wealth of knowledge and experience, which was evident every step of the way. We cannot recommend Kim more, and are grateful that she was part of our new home journey! (Our kids loved her too!)”
Wirtz Real Estate Group, Inc.
“Great job would recommend”
Century 21 Circle
“Great experience! Very attentive, honest, and dedicated. Professional, efficient, and easy to work with. Highly recommended!”
Century 21 Affiliated
“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.”
Century 21 Realty Associates
“Our experience with Laura was excellent. From the moment we reached out to her everything moved forward quickly. As a first-time seller, I felt comfortable throughout the entire process thanks to Laura's knowledge, accessibility, and responsiveness. She also took the time to understand and cater towards our specific needs. I would highly recommend Laura.”
Berkshire Hathaway Homeservices
“Shawn is a perfect example of everything a new homeowner could want in a realtor. He's patient, informative and passionate about helping you find the right home. Shawn goes the extra mile in preparing detailed documents on every listing you visit and has a vast knowledge of property pros and cons. You also know you'll get a honest and trustworthy professional at your side when you work with him. I can't recommend Shawn enough!”
Berkshire Hathaway HomeServices
“Brittany was wonderful to work with. I always felt like she was trying to help me get the house I wanted. It did not feel like she just wanted to sell me the first house to be done.”
Compass
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”
REALTY OF AMERICA
“Renee O'Brien was very understanding, helpful, and kind .... knowledgable in the house situation and problem solving to move the sale along swiftly...”
Keller Williams North Shore West
“Before using Jeffry as my agent, I had looked at several homes with 3 other agents for almost a year. Within 2 months of working with Jeffry, we found the home that I had been looking for and was the perfect fit.”
Berkshire Hathaway Home Services Chicago
“John Campobasso was great to work with in selling our unit. He was professional, knowledgeable, and guided us through every step of the process. We really appreciated how upfront and straightforward he was. He always gave us honest feedback and clear expectations. He made the whole experience feel smooth and much less stressful than we anticipated. We’re so glad we worked with him and would definitely recommend his services to anyone looking to buy or sell.”
Keller Williams Thrive Realty
“Great agent - professional, communicative, and results driven. I would highly recommend Steven to anyone buying or selling a home.”
RE/MAX Suburban
“I highly recommend Emir Vulic as a real estate agent. He is incredibly professional, kind, and truly cares about his clients. Emir always provided personalized attention, great market advice, and made sure every decision was in my best interest. He was responsive, trustworthy, and a pleasure to work with throughout the entire process. I’m very grateful for his guidance and would not hesitate to work with him again.”
Owners.com
““Working with Meldina Dervisevic to sell our single-family home in Wheeling was an excellent experience from start to finish. Her market knowledge, pricing strategy, and attention to detail helped us attract the right buyer quickly and confidently. Meldina guided us through every step of the process, communicated clearly, and handled negotiations with professionalism and care. Thanks to her expertise, our home sold smoothly and with great results. We highly recommend Meldina to anyone looking to sell their home.””
Century 21 Dream Homes
“Great to work with in all respects, from start to finish!”
Century 21 Affiliated
“Immediately upon meeting Tracy Anderson, I knew that she was the perfect realtor for us. Her local area sales experience, personal involvement and life history within the neighboring suburbs, the positive attitude she projects, and her light-hearted personality were unquestionably ideal for meeting our home selling goals. Tracy managed our sales process expertly and with ease, reflecting a humble confidence and control that created trust and excitement for us. We immediately realized her sales strategy would propel us smoothly to a gratifying sales experience. Prior to live posting on the MLS, we received multiple full price offers from the first day private showings. Tracy's clear communication and skilled negotiating with all involved parties, even prompted an above price offer. We could not be more elated with our time spent with Tracy and her very personal approach. Of course, I sincerely recommend her as a highly exceptional real estate agent.”
Compass
“Dan was very professional throughout the entire process. He was knowledgeable about the neighborhood and broader trends and we were able to respond quickly to market conditions. Dan is very fair, honest, and trustworthy. He is also candid about the condition of the property but strives to get the most value possible for the seller out of the sale. He hired a professional photographer which helped with marketing the property and bringing out its best features. We would recommend Dan to our family and friends.”
Century 21 SGR
“Kathryn went above and beyond. She worked the selling of the home while we were out of the country even. She was the perfect fit for us as an agent.”
Century 21 Affiliated
Frequently Asked Questions
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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 Southwest 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.
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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.
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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.
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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 Southwest Side Realtor® or real estate agent today.
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