“Kim was excellent, answered all my calls or texts promptly! If it was not part of her job she advised me who to contact ! Absolutely the Best”
Wirtz Real Estate Group, Inc.
- Agent Pronto
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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.
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 July 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
Mar 1, 2026 - May 31, 2026
Median sale price
$300K
+7.1%
from
Q1 '26
Median list price
$302K
+4.6%
from
Q1 '26
Active listings
1,223
+15%
from
Q1 '26
Homes sold
490
+40%
from
Q1 '26
New pendings
675
+23%
from
Q1 '26
New listings
706
+23%
from
Q1 '26
Quarterly Pricing Trends for Southwest Side
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Southwest Side
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Southwest Side
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Southwest Side
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Southwest Side
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Southwest Side
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
18
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Inventory on Chicago’s Southwest Side has been relatively steady in this rolling three-month view, with about 1,223 active listings, nearly flat compared with a year ago. New listings are also similar to last year, while homes sold are up around the mid–single digits year over year, indicating that more properties are getting to the closing table. Pending sales have risen at a similar pace, suggesting buyers are following through once homes go under contract.
Prices have been moving upward as this stronger contract flow meets limited new supply. The typical home value is up almost 7 percent from a year earlier, while the median list price has climbed nearly 10 percent, highlighting sellers’ growing confidence.
Time on market tells a more complex story in this rolling three-month snapshot. Median days on market is currently 58, much higher than a year ago, yet months of supply has edged down to about four months and the share of homes selling above list price is close to 38 percent. Compared with the broader city of Chicago, the Southwest Side offers significantly lower home values, which can attract value-focused buyers even as demand stays firm. With the area still tilted toward sellers but offering opportunities for buyers who act decisively, Agent Pronto can connect both buyers and sellers with an agent who understands these trends and can guide their next move.
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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“Excellent working with Mike McCatty highly recommend him and his services,thanks again Mike McCatty.”
Century 21 Circle
“Originally we were referred by our first lender and we could not have been more fortunate to work with Vicky and Sam. They were professional and realistic regarding our home search. We had not purchased a home in a very long time and Vicky was patient and understanding and was so attentive. avidly referred us to our second lender (the first was not communicative) and it was wonderful. Overall the whole experience was great! Thank you for helping us find our dream home!”
Berkshire Hathaway HomeServices Chicago
“Laura is Amazing!”
Berkshire Hathaway Homeservices
“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!”
Compass
“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”
RE/MAX Suburban
“Meldina is an expert in the local market and an exceptional negotiator. Her professionalism, communication, and dedication exceeded our expectations. We highly recommend her!”
Century 21 Dream Homes
“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.”
RE/MAX Remax Ultimate Professionals
“Kathy fought a lot of uphill battles for us and despite hurdles at every turn (with prospective buyer) she pushed on and was able to secure our sale. I can't thank her enough for the amount of work she put in.”
Berkshire Hathaway Chicago
“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.”
Century 21 Affiliated
“Brittany is an AMAZING realtor and I don't say that lightly. She goes above and beyond to make sure that we are getting everything that we asked for and more. If you are looking for a realtor that goes out of her way to make sure her clients needs are met, you have found your realtor! I could not put into words how happy I am!”
Compass
“Working with Emir is always a pleasure. He was very helpful in coordinating work on our house for sale, working with vendors and providing valuable feedback on neccesary work vs. potential work items unlikely to generate return. We closed sale of house 3 weeks from time of first listing. I'd worked with Emir before and hope to do so again in the future.”
Owners.com
“Melissa Young was incredibly attentive and knowledgeable which was critical for me as a first-time home buyer. She helped me win my very first bid with a strong offer and guided me through challenges with the appraisal process. She sets the bar high and I am so happy with my beautiful first home in Chicago!”
Berkshire Hathaway Home Services Chicago
“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
“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
“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
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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