We analyze top real estate agents in Chicago’s Southwest Side neighborhood and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for September 2025. *
* 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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“Working with Victoria Holmes was such a wonderful experience from start to finish. She made the whole process feel effortless, and her supporting staff was just as incredible—so kind, attentive, and genuinely invested in helping us. We keep pinching ourselves because this home is absolute perfection for our family. We’re beyond grateful to Victoria and her team for making this dream a reality.”
“Kim is the best. I shared with her that I had to sell my family members home and that I had 0 experience with realty or selling a home. She made everything so easy. The sale happened within days and I had no issues. She was there to help in a stressful time for me. I highly recommend.”
“Shawn came highly recommend and did not disappoint. He has been on the ball and on my side from begining to end. His local knowledge was invaluable as a buyer moving from out of state and his follow through with vetted vendors for after the purchase smoothed the transition. Shawn Jones is a man of his word and goes above and beyond.”
“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.”
“Kathryn Hoffman was recommended by a woman in our church book club. Kathryn lived up to the praises and compliments given by this person. She was professional and knowledgeable about every aspect of the home search and purchase process. Kathryn did her best to work around my schedule and was available for showings when necessary. Ms. Hoffman clearly understands the housing market and the many aspects and attributes of the communities in the Chicago suburbs. She was able to connect me with other experienced and respected professionals, as necessary during the purchase process (attorney, home inspector, etc). I would highly recommend Kathryn Hoffman as a realtor/agent.”
“Working with Mr Phillips was a pleasure, my property faced some challenges in regards the prospect buyers but he stepped in and quickly resolved the issues, Mr Phillips goes above and beyond and always makes sure his clients get the best treatment and deals. Cannot say enough how grateful I am working with him. I will definetely recommed him to my friends and family .”
“Cinny helped us sell and buy a condo at the same time and the whole experience was so smooth. From helping us list our place, going to showings with us, and answering all our concerns, I don’t know how she did it all but she was there for us. We were able to do both the selling and buying within 3 months which still amazes me how quick and easy she made this process. She was proactive in finding places and booking showings that work around our schedule. And what I really love is how well she understood what my partner and I were looking for in a home. We ended up buying the place she had suggested for us. Originally this place was not on our radar but she highly recommended us to check it out and we’re so glad we did. We’re so happy with new home and this could not have been done without Cinny!”
“John was a great Realtor many years of experience definitely knows his market. John is definitely one of the people that will get to know his sellers his clients and every time that I had any issues John always answered within an hour sometimes within minutes the funny thing is is that one day out of the blue John contacted me Wanting to know if I wanted to sell my house and I said you know I've been thinking about it cause I had a tenant in there and I have some severe medical problems and John waited and waited and waited through all the endless phone calls and follow ups. He ended up getting my business because he was patient. He waited and it took over a year of us working together to get my house on the market and it's sold in two weeks. I cannot say enough good things about John, but I do thank him for his patience and his understanding with my personal issue and I promised if he didn't give up on me, he would get the business and he got it!”
“Brittany was the best agent anyone can ask for always very informative and guided me threw all the steps as a first time home buyer I can not say enough about how amazing/professional she was as a first time home buyer i would recommend her to anyone who really wants someone to be in your corner on getting the perfect house that best suits your interest i found a home perfect for my family and it was all thanks to Brittany absolutely amazing 10/10”
“Nancy Silwa is an experienced realtor who knows her profession. She knows, and in fact lives in the area, where I was selling my house. This was a bonus as she really had a handle on the market. She walked with me every step of the way so that I understood the process. I was selling a home I had lived in for 43 years. Nancy understood the emotional impact of this decision and gently helped me stay focused on the task at hand: sell the house. She found the perfect buyers. A young couple who will make my house their home. Knowing this made selling my home a little easier. I would and indeed have recommended Nancy to others. She is simply THE BEST!”
“I can’t recommend Emir highly enough! From start to finish, he was professional, knowledgeable, and incredibly responsive. He truly had my best interests at heart and made the entire buying process smooth and stress-free. His attention to detail and dedication went above and beyond. If you’re looking for someone who knows the market and actually cares about their clients, Emir is the one!”
“Exceptional professional and person. Meldina was so kind and supportive through the entire process of buying my first commercial purchase.”
“Laura Topp was recommended by a trusted friend, a friend whom I will trust even more after this experience. Laura is extremely knowledgeable, personable and very well connected in the real estate market. Laura and her team (including Becki, also very involved in my sale and purchase) went over and above to insure my then-current home was sold in a timely manner (it was a matter of days, in fact) and for the best possible price! As for my purchase, Laura connected me with not only public but also private listings, and I also found/ contracted for my new dream home within days. In addition to her knowledge, expertise and connections, Laura is also one of the kindest people have ever met; she made me feel valued and supported throughout this entire process. I would recommend Laura and her team in a heartbeat (I already have) and although I was not previously aware of BHHS, this company also has high ratings in my book because of Laura and Becki.”
“Working with Tracy Anderson gave us a leg up. She is very knowledgeable of the market. She was very patient with my father. She staged the Home well using his furniture which made it look great. Her negotiating skills helped us through some potentially tricky issues and let us net the most possible. I would recommend her 100%!”
“My Wife and I were first time homebuyers in a very difficult market. Renee guided us through the process and answered any and all questions we had. We're extremely pleased with the end result and would happily work with her again in the future.”
“Antonio was always available for questions and always prompt in his replies. An ecellent experience.”
“We live in Florida and were wanting a second home in the Plainfield, Illinois area. We were not seeing too many places that were available. She showed us a few places in January online but they didn't work out for us. Since she knew what we were looking for, a condo went on the market that she thought we would be interested in. We happened to be in the Chicago area in March so we investigated the condo and sure enough we liked it and made an offer, and subsequently purchased. We were lucky that she remembered what we were looking for, and are so grateful to her for that, We also appreciated that she was not high pressure and that would have been an immediate turnoff for us. She was very helpful throughout the whole process and we would recommend her highly. Thanks again Kathy!”
“Steve is amazing! This sale was not easy, the contracted buyers were difficult but Steve negotiated for us, put us first, advocated for us, and he always presented all information. He is an agent who cares deeply about his clients and he is always working for the client not his wallet. I would refer and recommend Steve to anyone! He's absolutely amazing!”
“Karyn was amazing from the first contact. She was recommended by a close family friend, so I knew that I could rely on her. But the experience was even better that anticipated. She priced the house optimally to sell. Once an offer was received, Karyn took a reasonable approach to making a counter offer. She works in the best interest of the client. Karyn is maybe too accessible; some of my calls should hae gone to voice mail instead of her answering the phone. I have recommended Karyn to friends and family, and will continue to do so.”
“We were originally with a different agent looking for our first home when after a few months we transitioned to Mike Long. He has been involved in over a dozen real estate transactions within our family. When had our first call with Mike, we could tell he was an advocate for what we were looking for and positioned himself as someone we could trust navigating our home search. In one of the most challenging real estate markets and after looking at three dozen homes, we knew Mike was not a quitter. His optimism carried us through some of the most difficult weeks of our search. However, day in and day out, he brought humor, a shoulder to cry on and ensured that we didn’t stray from our core non-negotiables. Mike Long is an exceptional realtor.”
Information and statistics on the latest trends in the Southwest Side real estate market, updated for September 2025. *
The typical home value in Southwest Side is projected to be $290,000 for the month of September. August’s finalized data reported the typical value of a home in the neighborhood to be $290,000—up 1.75% over the previous 12 months. For comparison, city-level data pegged home values at $385,000 in Chicago for the most recent reporting period. That number is expected to float around $385,000 in September.
Southwest Side had 744 new listings and 641 listings that went under contract in August, decreasing the area’s total available inventory to 595—down 0.0% from the previous month. Inventory is projected to have further decreased in September.
The median listing price for homes in Southwest Side grew 3.21% from July to August, bringing the current median listing price to $289,000. Based on projected data for September, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract has been fairly steady year-over-year. In August 2025, the median time for a listed property to go pending was 58 days, compared to 61 days in August 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this September.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Southwest Side offers residents a vibrant blend of cultural diversity, rich history, and accessible community resources that foster a strong neighborhood spirit.
Southwest Side hums with everyday Chicago life, where sturdy bungalows, two-flats, and tidy lawns meet the energy of Chicago’s aviation gateway at Midway International Airport. Along commercial corridors in Garfield Ridge, Brighton Park, and Gage Park, you’ll find family-run taquerias, Polish bakeries, and old-school taverns, plus practical shopping at Ford City Mall. On weekends, neighbors gather for youth sports and picnics, or wander the lagoons and rolling greens of Marquette Park, one of the city’s grandest historic parks.
Education is a local point of pride. Families tap into a wide slate of Chicago Public Schools, including college-prep and career pathways, while adult learners and recent grads find upskilling opportunities at Richard J. Daley College. Cultural threads run deep here, showcased at the Balzekas Museum of Lithuanian Culture, and celebrated at block parties, parades, and neighborhood festivals that keep traditions alive.
Commuters appreciate straightforward travel: the CTA Orange Line speeds to the Loop, and Midway’s quick check-ins make weekend getaways painless. Housing tends to offer more space for the price, with garages and backyards common—an easy fit for gardeners, hobbyists, and anyone who loves a summer barbecue.
Thinking about buying or selling on the Southwest Side? Agent Pronto can quickly connect you with a proven local real estate agent who knows the block-by-block nuances and can help you move with confidence.
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.
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.
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