We analyze thousands of real estate agents in Chicago’s Woodlawn neighborhood and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for August 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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Information and statistics on the latest trends in the Woodlawn real estate market. *
Apr 1, 2026 - Jun 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Apr 2026 - Jun 2026).
Woodlawn’s rolling three-month snapshot shows inventory and activity picking up. Active listings are up nearly 10% year over year, reaching 178 homes on the market. Contract flow is also stronger, with homes sold rising about 20% and new listings up roughly 24% compared with a year ago.
Pricing is responding to this momentum. The typical home value over the period is about $400,000, up a little more than 23% year over year, while the median list price is up more modestly, around 3%. Sellers are often close to their asking prices, with the average sale-to-list ratio near 99%, and about 28% of sales closing above list, a share that has grown over the past year.
Conditions point to a market that gives both sides some leverage. Months of supply sits at about five months in Woodlawn, higher than Chicago’s 2.8 months, which suggests buyers have more options locally even as demand stays solid. Homes are taking longer to sell than a year ago, at a median of 73 days on market, yet nearly 40% still go off market within two weeks, showing quick movement for well-priced properties. Whether you are a buyer trying to navigate these shifts or a seller aiming to price confidently, Agent Pronto can connect you with a local agent who understands the Woodlawn market.
Woodlawn offers residents a dynamic blend of community, culture, and opportunity, with parks, local businesses, and engaged neighbors shaping a welcoming, resilient neighborhood.
Woodlawn in Chicago stands out from nearby Hyde Park and South Shore with a strong sense of local identity and a wave of thoughtful reinvestment. Anchored by the University of Chicago to the north and the future Obama Presidential Center in nearby Jackson Park, Woodlawn offers a rare blend of long-established community roots and emerging opportunity.
Residents enjoy easy access to sprawling Jackson Park for lakefront trails, golf, and birding, while Washington Park is just to the west with major cultural and sports facilities. The 63rd Street Beach and Lake Michigan are minutes away, giving the neighborhood a connection to the water that many South Side communities covet. Local spots such as Robust Coffee Lounge and neighborhood restaurants along 63rd and Cottage Grove reflect a growing dining scene grounded in community ownership.
Housing in Woodlawn ranges from classic Chicago flats and greystones to new townhomes and apartment buildings, attracting long-time residents, first-time buyers, and investors. Proximity to Metra Electric stops, CTA Green Line stations, and quick access to Downtown Chicago keeps commutes straightforward and supports strong long-term potential.
With major projects underway and prices evolving, timing and preparation are crucial. Whether you are planning to buy into Woodlawn’s next chapter or sell to capture current demand, Agent Pronto can connect you with a local real estate agent who understands this neighborhood and how to navigate its shifting market for both buyers and sellers.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“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.”
“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.”
“We had an amazing experience working with Andrew at Century 21 Circle! From the very beginning, Andrew was incredibly knowledgeable, patient, responsive, and always willing to go above and beyond for us. He was quick to respond to every question and did everything he could to get us into showings, even when we needed to move quickly or work around our schedules. Buying a home can be stressful, but Andrew made the process feel so much easier. We always felt like he had our best interests in mind and genuinely wanted to help us find the right home. We couldn’t have asked for a better realtor and are so grateful for everything he did to help us find our home! If you’re looking for a realtor, we highly recommend Andrew and the team at Century 21 Circle!”
“Kim was easy to work with. She explained everything very clearly, which was something important to me as a first time seller. Her attention to detail and open communication were greatly appreciated and I highly recommend working with her.”
“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!”
“We've known Brittany for many years and we have had experience working with her in the past. We chose to work with her once more because of our wonderful experience In the past. I would highly recommend her because of her professional approach and her genuine interest to provide the best to her customers.”
“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!”
“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.”
“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.”
“Vicky knows real estate and has excellent communication skills. She relayed her recommendations and expectations. Her experience expedited the sale of my home. I had a contract in less than two days. She is a hard worker and always available to respond to questions or concerns. I highly recommend her for an agent.”
“Melissa Young is an excellent realtor. I highly recommend her.”
“Laura is Amazing!”
“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!”
“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”
“Meldina is an expert in the local market and an exceptional negotiator. Her professionalism, communication, and dedication exceeded our expectations. We highly recommend her!”
“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.”
“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.”
“Working with Kolby Banks was an exceptional experience. His professionalism, deep market knowledge, and proactive communication turned a complex process into a seamless one. Kolby is a sharp negotiator who truly advocates for his clients' best interests. If you want a realtor who is transparent, detail-oriented, and results-driven, we highly recommend Kolby Banks. He’s simply the best in the business!”
“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.”
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”
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 Woodlawn. 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.
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 Woodlawn Realtor® or real estate agent today.
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