- Agent Pronto
- Illinois
- Chicago
- Woodlawn
Find the perfect real estate agent in Woodlawn, Chicago, IL
We analyze top real estate agents in Chicago’s Woodlawn neighborhood and across the country to find you the most proven local agents, for free.
Compare the top 25 real estate agents in Woodlawn
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for May 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.
The easiest way to find the best real estate agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
Home buyers and sellers love Agent Pronto.
Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.
“Working with James was a terrific experience. He is most knowledgeable and realistic when evaluating real estate. He always kept me informed and had timely calls regarding our next decisions. I recommend him most highly.”
“Steve rocks! He was on top of things and kept me informed as issues arose. He pulled me off the ledge a few times and he was surprised that I called to thank him after the closing. He's a keeper.”
“Mike Frank provided excellent service and was a pleasure to work with.”
“Dena was absolutely incredible. I could not be happier.”
“It's been great working with Bobbi - she is very responsive (never once missed a phone call or text), always on point but never pushy, be it her advice on pricing changes or negotiating an offer or following up on repairs. She arranged multiple open houses, brought in a steady stream of potential buyers, helped us a lot thru the whole process, made it easy for us even after we moved out of state and got our home sold just before the winter hit. Loved working with her and would definitely recommend her. ”
“Cheri Gibson was the best I have ever dealt with. She was professional at all times. She answered all our questions. She is very knowledgeable. I would highly recommend her to anyone looking to sell/buy. The house was listed and sold in one day.”
“It was great! We were put in touch with the best real estate agent around!”
“Thank you, Agent Pronto, for recommending Karl. He was an amazing agent and just got the job done! I would recommend your service and Karl to any future home sellers or buyers!!!”
“I would recommend Nancy Silwa to someone I knew who was looking for a house first time, or someone who wanted to sell their house. I will miss her because we had a bond more than just a client. She is the kindest, caring, loving, professional individual I have ever met. If you want someone who goes beyond her duties on your behalf, hire her. ”
“Sergio met the timeline, and he provided valuable knowledge and advice. The supporting legal reps that he recommended did an outstanding job. ”
Woodlawn real estate Market Report.
Information and statistics on the latest trends in the Woodlawn real estate market, updated for May 2025. *
The typical home value in Woodlawn is projected to be $333,250 for the month of May. April’s finalized data reported the typical value of a home in the neighborhood to be $335,000—up 31.37% over the previous 12 months. For comparison, city-level data pegged home values at $394,490 in Chicago for the most recent reporting period. That number is expected to float around $396,790 in May.
Woodlawn had 89 new listings and 62 listings that went under contract in April, increasing the area’s total available inventory to 97—up 5.43% from the previous month. Inventory is projected to have further increased in May.
The median listing price for homes in Woodlawn fell 5.88% from March to April, bringing the current median listing price to $340,000. Based on projected data for May, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In April 2025, the median time for a listed property to go pending was 67 days, compared to 29 days in April 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this May.
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 Woodlawn has to offer.
Woodlawn offers residents a vibrant community filled with cultural diversity, historical charm, and numerous opportunities for neighborhood revitalization.
Woodlawn offers an exciting blend of culture, history, and ongoing renewal on Chicago’s South Side. Just steps from the University of Chicago and the stately Midway Plaisance, Woodlawn is quickly gaining attention for its dynamic transformation anchored by new investments and a creative spirit. The forthcoming Obama Presidential Center, rising at the neighborhood’s northern edge, promises to be both a cultural institution and an economic catalyst, drawing visitors and energizing local businesses.
Families appreciate the educational opportunities at University of Chicago Laboratory Schools and Woodlawn Community School. Recreation beckons with green open spaces like Jackson Park, where serene lagoons, a golf course, and extensive trails invite leisure and play. Neighborhood eateries and coffee shops channel South Side tradition and ingenuity, while Robust Coffee Lounge serves as a lively meeting spot.
Woodlawn’s proximity to Hyde Park, convenient access to downtown, and a strong sense of community are drawing both longtime Chicagoans and newcomers. Whether drawn by the neighborhood’s storied past or its promising future, residents discover a place where diversity, progress, and partnership fuse. If you’re considering selling a home or searching for the perfect place to put down roots, Agent Pronto can seamlessly connect buyers and sellers with top local real estate agents experienced in Woodlawn’s unique market.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
Take the guesswork out of finding an agent.
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Woodlawn to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Data analysis with a human touch.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Chicago. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!
Resources for buyers and sellers.
Tips and market insights to make your Chicago real estate journey a success.
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. 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.
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