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Real estate in Chicago’s Southwest Side neighborhood.

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 October 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. *

Latest Rolling 3-Month Snapshot

Jul 1, 2026 - Sep 30, 2026

Median sale price
$310K
-0% from Q2 '26
Median list price
$326K
+5.1% from Q2 '26
Active listings
1,249
-0.4% from Q2 '26
Homes sold
516
-2.3% from Q2 '26
New pendings
606
-6.2% from Q2 '26
New listings
664
-6.5% from Q2 '26

Quarterly Pricing Trends for Southwest Side

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Southwest Side Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $253K Median sale price in Jan 2022 - Mar 2022: $245K Median sale price in Apr 2022 - Jun 2022: $260K Median sale price in Jul 2022 - Sep 2022: $246K Median sale price in Oct 2022 - Dec 2022: $245K Median sale price in Jan 2023 - Mar 2023: $234K Median sale price in Apr 2023 - Jun 2023: $260K Median sale price in Jul 2023 - Sep 2023: $259K Median sale price in Oct 2023 - Dec 2023: $259K Median sale price in Jan 2024 - Mar 2024: $257K Median sale price in Apr 2024 - Jun 2024: $275K Median sale price in Jul 2024 - Sep 2024: $285K Median sale price in Oct 2024 - Dec 2024: $278K Median sale price in Jan 2025 - Mar 2025: $273K Median sale price in Apr 2025 - Jun 2025: $285K Median sale price in Jul 2025 - Sep 2025: $295K Median sale price in Oct 2025 - Dec 2025: $285K Median sale price in Jan 2026 - Mar 2026: $280K Median sale price in Apr 2026 - Jun 2026: $310K Median sale price in Jul 2026 - Sep 2026: $310K Median list price in Oct 2021 - Dec 2021: $249K Median list price in Jan 2022 - Mar 2022: $250K Median list price in Apr 2022 - Jun 2022: $255K Median list price in Jul 2022 - Sep 2022: $255K Median list price in Oct 2022 - Dec 2022: $235K Median list price in Jan 2023 - Mar 2023: $245K Median list price in Apr 2023 - Jun 2023: $255K Median list price in Jul 2023 - Sep 2023: $259K Median list price in Oct 2023 - Dec 2023: $269K Median list price in Jan 2024 - Mar 2024: $259K Median list price in Apr 2024 - Jun 2024: $287K Median list price in Jul 2024 - Sep 2024: $275K Median list price in Oct 2024 - Dec 2024: $267K Median list price in Jan 2025 - Mar 2025: $280K Median list price in Apr 2025 - Jun 2025: $284K Median list price in Jul 2025 - Sep 2025: $290K Median list price in Oct 2025 - Dec 2025: $283K Median list price in Jan 2026 - Mar 2026: $289K Median list price in Apr 2026 - Jun 2026: $310K Median list price in Jul 2026 - Sep 2026: $326K Oct 2021 - Dec 2021 Median sale price $253K Median list price $249K Jan 2022 - Mar 2022 Median sale price $245K Median list price $250K Apr 2022 - Jun 2022 Median sale price $260K Median list price $255K Jul 2022 - Sep 2022 Median sale price $246K Median list price $255K Oct 2022 - Dec 2022 Median sale price $245K Median list price $235K Jan 2023 - Mar 2023 Median sale price $234K Median list price $245K Apr 2023 - Jun 2023 Median sale price $260K Median list price $255K Jul 2023 - Sep 2023 Median sale price $259K Median list price $259K Oct 2023 - Dec 2023 Median sale price $259K Median list price $269K Jan 2024 - Mar 2024 Median sale price $257K Median list price $259K Apr 2024 - Jun 2024 Median sale price $275K Median list price $287K Jul 2024 - Sep 2024 Median sale price $285K Median list price $275K Oct 2024 - Dec 2024 Median sale price $278K Median list price $267K Jan 2025 - Mar 2025 Median sale price $273K Median list price $280K Apr 2025 - Jun 2025 Median sale price $285K Median list price $284K Jul 2025 - Sep 2025 Median sale price $295K Median list price $290K Oct 2025 - Dec 2025 Median sale price $285K Median list price $283K Jan 2026 - Mar 2026 Median sale price $280K Median list price $289K Apr 2026 - Jun 2026 Median sale price $310K Median list price $310K Jul 2026 - Sep 2026 Median sale price $310K Median list price $326K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
21
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

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.

Find your Southwest Side real estate agent today →


Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“We had such a great experience working with Victoria and Sam! They were always quick to respond whenever we sent a home we were interested in or had questions. They were willing to go on as many tours as it took to help us find the right fit and were honest about steering us away from homes with structural concerns. It was clear they genuinely had our best interests at heart and wanted us to find a home we’d love. They’re also both funny and easy to get along with, which made the entire process that much more enjoyable. We couldn’t recommend them enough!”

Caden Burgess · Wilmington, IL

Photo of Victoria Holmes
Berkshire Hathaway HomeServices Chicago
“Kim Wirtz A fantastic sales person,Thank you very much for selling my property in such a short time.”

Tracy Lin · Midlothian, IL

Photo of Kim Wirtz
Wirtz Real Estate Group, Inc.
“I highly recommend working with Meldina! She is incredibly accommodating and always willing to show the properties, even on the short notice. She is very knowledgeable about the location we are exploring and her positive attitude, amazing energy and solution oriented mindset truly make a difference.Her professionalism and enthusiasm make the entire experience enjoyable. Thank you, Meldina, for you outstanding support and dedication.”

Alma A · Skokie, IL

Photo of Meldina Realty Group
Century 21 Dream Homes
“Jose made the process incredibly smooth is first-time buyers.”

Fernando · Joliet, IL

Photo of Jose Alarcon
Realty of America
“Selling our first home was emotional, and we couldn’t have asked for a better realtor than Brittany. When our first offer fell through, she had us under contract with a second offer within 24 hours! Her unwavering confidence and steady reassurance helped us feel at ease during such an uncertain time, especially as first-time sellers. Brittany supported us every step of the way, always making time to listen, answer our questions, and talk through our concerns. We felt heard, cared for, and confident that she had our best interests at heart. This was our second real estate transaction with Brittany, and we would never work with anyone else. We’re so grateful for her dedication, expertise, and kindness. We cannot recommend her highly enough!”

Vanessa Peters · Lombard, IL

Photo of Brittany Simon
Compass
“Renee was very helpful in our search for a house. She was very friendly, knowledgeable and very easy going personality. She and her office assistant were always available if there were any questions”

Angela Diaz · Arlington Heights, IL

Photo of Renee OBrien Group
Keller Williams North Shore West
“I can’t say enough wonderful things about Steve Goodman and the experience we’ve had working with him over the past 10 years. Steve was my realtor when I purchased my very first condo, and 10 years later, he was right there with us as we sold that condo and purchased what we hope will be our forever home. Having the opportunity to work with the same realtor through such an important chapter of our lives speaks volumes about the trust and confidence we have in him. What sets Steve apart is that he genuinely puts his clients’ best interests first. He is never pushy or focused on simply making a sale. Instead, he takes the time to listen, answer every question, offer honest advice, and make sure you feel comfortable with every decision. He is incredibly patient, knowledgeable, and always willing to go the extra mile.”

Joanna · Des Plaines, IL

Photo of Steven Goodman
RE/MAX Suburban
“Was impressed from the beginning when the owner answered the phone and made an appointment within a day or two to come out to the property. When we decided to put the house on the market, they were extremely professional And answered all our questions. The photographer came out promptly, and took amazing pictures of the property. It was listed the next day,and our house sold in less than a week. Andrew McCatty was our broker. He could not have been more knowledgeable or professional. Any questions that we had, Andrew either answered the phone or got back to us very quickly. Highly recommend Andrew and Century 21 Circle. Would only work with them again and would recommend them to family and friends.”

Debbie · Burnham, IL

Photo of McCatty Real Estate
Century 21 Circle
“Jeff is a knowledgeable professional. Trustworthy who will give you excellent feedback and advice”

Vin Peseski · Naperville, IL

Photo of Jeff Coros Team
Century 21 Affiliated
“Barb was a pleasure to work with, and I would highly recommend her to anyone.”

George Stell · Minooka, IL

Photo of Barb Gall
RE/MAX Remax Ultimate Professionals
“We were referred to Tracy in our move from downtown to the suburbs, and we couldn’t have asked for a better experience. She made what can be a stressful process feel easy and manageable from start to finish. Tracy was both professional and personal, detail-oriented, responsive, and always quick to act when it mattered. Her deep knowledge of the local market and strong connections were invaluable throughout our purchase. We would wholeheartedly recommend Tracy to anyone looking to buy a home!”

The Claussen Family · Hinsdale, IL

Photo of Tracy Anderson
Compass
“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.”

John MacRitchie · Chicago, IL

Photo of The Jones Group
Berkshire Hathaway HomeServices
“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.”

Job Ojo · Plainfield, IL

Photo of Rose Riordan
Century 21 Affiliated
“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!”

Merim Vilic · Des Plaines, IL

Photo of Emir Vulic
Owners.com
“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!”

Luke Turck · Chicago, IL

Photo of Paula Calzolari
Berkshire Hathaway Starck Real Estate
“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.”

Tiffany · Chicago, IL

Photo of Jeff Phillips
Berkshire Hathaway Home Services Chicago
“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.”

Dan Coglianese · Orland Park, IL

Photo of Househunters4u Team
Berkshire Hathaway Chicago
“Melissa Young is an excellent realtor. I highly recommend her.”

Michael Withers · Chicago, IL

Photo of Melissa Young
Berkshire Hathaway Home Services Chicago
“Working with Bryce was a fantastic experience! He is professional, knowledgeable and went above and beyond at every step of the process. He took the time to truly understand what I was looking for in a new home and he expertly negotiated on my behalf. I would highly recommend Bryce to anyone who is looking for a dedicated real estate agent who has your best interest.”

Katie · Oak Lawn, IL

Photo of Bryce Buck
Elevate - The Real Estate Company
“Laura is Amazing!”

Stephen Brady · Chicago, IL

Photo of Topp team
Berkshire Hathaway Homeservices

Frequently Asked Questions

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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