“Kim was a pleasure to work with. Great experience with Kim all the way around.”
- Agent Pronto
- Illinois
- Chicago
- Southwest Side
The best way to find top real estate agents in Southwest Side, Chicago, IL
We analyze thousands of real estate agents in Chicago’s Southwest Side neighborhood and nationwide to find you proven local professionals, for free.
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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 November 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.
The easiest way to find a top agent you can trust.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
- Tell us what you need.
- Answer a few quick questions about your real estate goals.
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- Whether you’re buying, selling, or both, you’ll have a proven expert on your side.
Southwest Side real estate Market Report.
Information and statistics on the latest trends in the Southwest Side real estate market. *
Latest Rolling 3-Month Snapshot
Jul 1, 2026 - Sep 30, 2026
Quarterly Pricing Trends for Southwest Side
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Southwest Side
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Southwest Side
Rolling three-month data ending on quarter boundaries when available.
Quarterly Inventory and Sales Activity for Southwest Side
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Southwest Side
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Southwest Side
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 (Jul 2026 - Sep 2026).
Inventory on Chicago’s Southwest Side has tightened slightly in this rolling three-month view, with active listings down about 5% from a year ago. New listings and closed sales have also slipped year over year, signaling a bit less turnover even as 606 homes went under contract. With months of supply rising to 3.7 and the market gauge still pointing to a seller’s market, conditions lean toward sellers but with more balance than in past years.
Home values have moved up over the past year, with the typical sale price on the Southwest Side increasing about 5% while the city of Chicago overall rose closer to 8%. Asking prices have climbed even faster, with median list price up more than 12% year over year, suggesting sellers are testing higher price points.
Despite those higher list prices, buyers are still bidding strongly on well-priced homes. Nearly 42% of recent sales closed above asking, and the typical home is selling for essentially full list price, at just under 100% of asking. Homes are taking slightly longer to sell than a year ago, with median days on market now around 59, but almost 46% still go off-market within two weeks. With these mixed signals, both buyers and sellers on the Southwest Side can benefit from Agent Pronto’s help in finding an agent who understands current pricing and pace in this neighborhood.
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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“Daniel had helped us in the past with the purchase of our first home so it was an easy decision when we decided it was time to move again to use him. He was accommodating, helpful and gave insight when we were looking for a new house in a new area. He listened to our wants and pointed things out we may not have noticed ourselves. This time we used Daniel for the sale of our condo and the purchase of our new home and was attentive, engaged & made both the purchase and sale happen seamlessly. I highly recommend Daniel to anyone selling or buying! With him you will find someone who genuinely wants to help with the difficult process of buying / selling.”
“Laura is hard working, dedicated, and responsive. She understood the challenges of a cash-only sale and made things happen that would have been dropped by less motivated realtors. As my listing agent she closed a sale on a property that was very difficult to sell at a sales price that other realtors balked at. She earned every penny of her commission. Hire her! You won’t regret it.”
“Selling our condo was a much smoother experience than I expected, and I truly have Larry to thank for that. From the very beginning, he was knowledgeable, responsive, and incredibly professional. Night or Day, weekday or weekend Larry answered the phone and communicated actively any information about the process to us. A true professional. He guided us through every step of the process, answered all of my questions, and always made us feel confident in the decisions we were making. What impressed me most was his negotiation skills. Larry advocated for our best interests every step of the way and worked hard to secure the best possible outcome. We always felt like he had our back and never settled for less than what our home was worth. If you’re looking for an agent who is honest, strategic, communicative, and genuinely invested in their clients, we can’t recommend Larry Lazar highly enough. Selling a home can be stressful, but he made the entire process seamless. We would absolutely work with him again and recommend him to anyone buying or selling a home.”
“Cannot emphasize enough how helpful Brad was during this whole process. We had literally zero idea about what we were doing and he helped in so many ways.”
“Working with Henry and the Heart of Chicago Homes team was an incredible experience from start to finish. Throughout the entire process, I always felt supported, informed, and confident knowing he and the team had our best interests in mind. We were searching in one of the most competitive markets, and the townhome we fell in love with ended up receiving multiple offers. Although our offer wasn’t accepted initially, Henry stayed persistent and maintained consistent communication with the listing agent. Thanks to his dedication and follow-up, he was able to position us next in line and ultimately help us secure our dream home when the first deal fell through. Even though we originally had the second-best offer, his hard work, relationships, and determination made all the difference. We couldn’t be more grateful and would highly recommend Henry and his team to anyone looking to buy or sell a home!”
“We cannot thank Mike and his team enough for their hard work. They are the definition of professional and were always one step ahead, keeping us informed every step of the way. They made what can usually be a stressful process feel incredibly easy and made the entire process seamless. They truly get things done. Highly recommend!”
“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.”
“Jakeshia Thomas provided a great service. She helped us navigate a concurrent closing deal involving multiple real estate transactions, She repeated us, the buyers. She went above and beyond, making our real estate experience smooth and stress-free. Her level of professionalism and patience when working with first-time is unmatched. I can’t say enough positive things about her.”
“We had an amazing experience working with Primal and cannot recommend him highly enough! From the beginning, he was incredibly responsive to every question we had—no matter how big or small. We truly appreciated how kind and patient he was with us, especially as we changed our minds multiple times about location and price. He never made us feel rushed or pressured, and instead took the time to help us find the right fit. What really stood out was how honest and down-to-earth he is. He pointed out things we would have never considered on our own, which made us feel informed and confident in our decision-making process. It was clear he genuinely had our best interests at heart. He worked so hard on our behalf and ultimately helped us secure a beautiful apartment that checked all of our (many) boxes. Even with his busy schedule, he consistently went above and beyond in his communication and support. Primal is everything you could want in a realtor: knowledgeable, honest, kind, compassionate, and friendly. We HIGHLY recommend working with him for any real estate needs, whether you're looking to rent an apartment or buy a house. He will go above and beyond to help you find exactly what you're looking for!”
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”
“Reggie was amazing and so supportive through the whole process. He always took the time to explain anything that was confusing to me as a first time home buyer and he helped me find everyone else I needed to help me with the home buying process like a loan processor and attorney and everything. Highly recommend him to anyone and everyone!”
“Eicka did an outstanding job with selling my hope. She was knowledgeable and she provided a speedy process. Her communication and negotiation skills were amazing. She is also incredibly personable-making communication easy. She also shares a great deal of appreciation to her clients. I highly recommend her support and expertise in the business of realty. Whether you are a buyer, seller, or need guidance-she will be an asset to your journey.”
“She was very helpful especially to a first time home buyer. Whatever questions I had about the property she would answer it or get the answer from the listing agent. Was always on time for showings. Would definitely recommend her especially for first time buyers”
“She's was amazing from start to finish. Helped me close as soon as possible. And spent time helping find our perfect home. Set us with a great lawyer! She worked well on communication and keeping us informed throughout the process. She did so well that I recommended to help my mother sell her home.”
“Kat was simply amazing! I was a first time buyer with a lot of gaps in my knowledge and she was super about answering my questions, responding to my last minute “wait what about..” moments and just educating me about what the expect. She is someone who clearly gets a lot out of helping folks find their perfect place and was always the first to ask the tough questions that I didn’t think to/know you could ask!”
“Miguel was amazing 10/10 definitely recommend! He is very knowledgeable and super attentive, he really made this first time home buying process very smooth and the best of all is that he was very understanding.”
“Juan helped us immensely in buying our first home and answered every question we had. Would 100% recommend.”
“Antonio was always available for questions and always prompt in his replies. An ecellent experience.”
“Thalia is an amazing realtor! 10/10! 5 stars! As a first time home buyer, I did not know what to expect or what the process of buying a home was. Thalia was amazing when she sat down with me and walked me through each and every step. She is extremely knowledgeable, and always available. I really appreciated her efficiency; Thalia works at the buyers pace, and when she says something will get done…..it gets done. She was always available to answer any and all of my questions….at anytime of the day! I am so happy Thalia was my realtor, and if I ever need to buy or sell a property, I will be calling Thalia back.”
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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