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Find the perfect real estate agent in West Woodlawn, Chicago, IL
We analyze top real estate agents in Chicago’s West Woodlawn neighborhood and across the country to find you the most proven local agents, for free.
Compare the top 25 real estate agents in West 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.
“Excellent! Very pleased with the process and the agent I chose to work with. It was expedient and simple, which worked perfectly for me as I'm located in another state away from the property I sold!!”
“Mike Frank provided excellent service and was a pleasure to work with.”
“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.”
“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!!!”
“Dena was amazing! She helped us tremendously...She helped us with a new lender and made our dream come true, and not even Covid-19 stopped us! Forever grateful. ”
“It was great! We were put in touch with the best real estate agent around!”
“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'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. ”
“Jodi got the job done!”
“The request was responded to by three different potential agents and I was able to finalize my selection the same day. John Campobasso worked out great. This was a very difficult and complicated sale, and he was great navigating the multiple parties involved to get this to a completed transaction.”
West Woodlawn real estate Market Report.
Information and statistics on the latest trends in the West Woodlawn real estate market, updated for May 2025. *
The typical home value in West Woodlawn is projected to be $407,250 for the month of May. April’s finalized data reported the typical value of a home in the neighborhood to be $399,000—down 18.55% 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.
West Woodlawn had 35 new listings and 28 listings that went under contract in April, increasing the area’s total available inventory to 47—up 4.44% from the previous month. Inventory is projected to have further increased in May.
The median listing price for homes in West Woodlawn fell 0.0% from March to April, bringing the current median listing price to $399,000. 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 78 days, compared to 69 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 West Woodlawn has to offer.
West Woodlawn offers residents a vibrant community with rich cultural history, diverse local amenities, and opportunities for urban renewal.
West Woodlawn offers a compelling blend of historic charm, community pride, and renewed vibrancy in the heart of Chicago. Residents and potential newcomers appreciate its proximity to both the Washington Park neighborhood and the natural allure of Jackson Park, placing world-class recreation, birdwatching, and scenic strolls just a few minutes from home. The neighborhood is also within easy reach of the highly anticipated Obama Presidential Center, which is expected to infuse even more energy and investment into the area.
Families living in West Woodlawn enjoy access to educational opportunities through schools like Andrew Carnegie Elementary School and the University of Chicago Laboratory Schools, supporting both strong academics and a sense of community. The Arts Block, championed by the Arts + Public Life Initiative, offers creative hubs and collaborative spaces that nurture local artists and incubate cultural events throughout the year.
Food enthusiasts will delight in nearby gems such as Daley's Restaurant, a staple of the Greater Grand Crossing area, or the inventive menu at Peach's on 47th. Convenient access to the CTA Green Line at the 63rd and Cottage Grove station places the wider city, including Hyde Park and downtown Chicago, within effortless reach.
With a long legacy of civic engagement and strong block clubs, West Woodlawn continues to grow as a welcoming community for buyers and sellers alike. Agent Pronto is ready to connect you with a knowledgeable local agent, whether you are seeking the perfect new home or looking to list your current property in this evolving neighborhood.
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 West 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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