The best way to find top real estate agents in Woodlawn, Chicago, IL

We analyze thousands of real estate agents in Chicago’s Woodlawn neighborhood and nationwide to find you proven local professionals, for free.

Find Your Perfect Agent

Ready to get started?


  • Client Testimonials
  • Local Market Reports
  • Tailored Recommendations
  • Free Home Value Estimates
  • Agent Sales Histories
  • Free, No Obligation
Real estate in Chicago’s Woodlawn neighborhood.

Compare top Woodlawn real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 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.

The easiest way to find a top agent you can trust.

Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.

Tell us what you need.
Answer a few quick questions about your real estate goals.
Get matched.
We’ll find you top local agents based on performance, expertise, and customer reviews.
Connect and compare.
Review your personalized recommendations and choose who’s right for you.
Move forward with confidence.
Whether you’re buying, selling, or both, you’ll have a proven expert on your side.
Agent profile screenshot
Agent profile screenshot

Woodlawn real estate Market Report.

Information and statistics on the latest trends in the Woodlawn real estate market. *

Latest Rolling 3-Month Snapshot

Jul 1, 2026 - Sep 30, 2026

Median sale price
$307K
-21% from Q2 '26
Median list price
$351K
+8.8% from Q2 '26
Active listings
162
-1.8% from Q2 '26
Homes sold
47
-15% from Q2 '26
New pendings
67
+12% from Q2 '26
New listings
78
-10% from Q2 '26

Quarterly Pricing Trends for Woodlawn

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Woodlawn Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $301K Median sale price in Jan 2022 - Mar 2022: $235K Median sale price in Apr 2022 - Jun 2022: $280K Median sale price in Jul 2022 - Sep 2022: $277K Median sale price in Oct 2022 - Dec 2022: $215K Median sale price in Jan 2023 - Mar 2023: $327K Median sale price in Apr 2023 - Jun 2023: $275K Median sale price in Jul 2023 - Sep 2023: $273K Median sale price in Oct 2023 - Dec 2023: $240K Median sale price in Jan 2024 - Mar 2024: $180K Median sale price in Apr 2024 - Jun 2024: $275K Median sale price in Jul 2024 - Sep 2024: $370K Median sale price in Oct 2024 - Dec 2024: $288K Median sale price in Jan 2025 - Mar 2025: $305K Median sale price in Apr 2025 - Jun 2025: $322K Median sale price in Jul 2025 - Sep 2025: $245K Median sale price in Oct 2025 - Dec 2025: $275K Median sale price in Jan 2026 - Mar 2026: $287K Median sale price in Apr 2026 - Jun 2026: $390K Median sale price in Jul 2026 - Sep 2026: $307K Median list price in Oct 2021 - Dec 2021: $260K Median list price in Jan 2022 - Mar 2022: $300K Median list price in Apr 2022 - Jun 2022: $269K Median list price in Jul 2022 - Sep 2022: $259K Median list price in Oct 2022 - Dec 2022: $325K Median list price in Jan 2023 - Mar 2023: $315K Median list price in Apr 2023 - Jun 2023: $360K Median list price in Jul 2023 - Sep 2023: $363K Median list price in Oct 2023 - Dec 2023: $290K Median list price in Jan 2024 - Mar 2024: $329K Median list price in Apr 2024 - Jun 2024: $325K Median list price in Jul 2024 - Sep 2024: $348K Median list price in Oct 2024 - Dec 2024: $281K Median list price in Jan 2025 - Mar 2025: $354K Median list price in Apr 2025 - Jun 2025: $300K Median list price in Jul 2025 - Sep 2025: $278K Median list price in Oct 2025 - Dec 2025: $343K Median list price in Jan 2026 - Mar 2026: $340K Median list price in Apr 2026 - Jun 2026: $323K Median list price in Jul 2026 - Sep 2026: $351K Oct 2021 - Dec 2021 Median sale price $301K Median list price $260K Jan 2022 - Mar 2022 Median sale price $235K Median list price $300K Apr 2022 - Jun 2022 Median sale price $280K Median list price $269K Jul 2022 - Sep 2022 Median sale price $277K Median list price $259K Oct 2022 - Dec 2022 Median sale price $215K Median list price $325K Jan 2023 - Mar 2023 Median sale price $327K Median list price $315K Apr 2023 - Jun 2023 Median sale price $275K Median list price $360K Jul 2023 - Sep 2023 Median sale price $273K Median list price $363K Oct 2023 - Dec 2023 Median sale price $240K Median list price $290K Jan 2024 - Mar 2024 Median sale price $180K Median list price $329K Apr 2024 - Jun 2024 Median sale price $275K Median list price $325K Jul 2024 - Sep 2024 Median sale price $370K Median list price $348K Oct 2024 - Dec 2024 Median sale price $288K Median list price $281K Jan 2025 - Mar 2025 Median sale price $305K Median list price $354K Apr 2025 - Jun 2025 Median sale price $322K Median list price $300K Jul 2025 - Sep 2025 Median sale price $245K Median list price $278K Oct 2025 - Dec 2025 Median sale price $275K Median list price $343K Jan 2026 - Mar 2026 Median sale price $287K Median list price $340K Apr 2026 - Jun 2026 Median sale price $390K Median list price $323K Jul 2026 - Sep 2026 Median sale price $307K Median list price $351K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
24
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).

Woodlawn’s rolling three-month snapshot shows a market with steady activity and ample choices for shoppers. Active listings are up modestly year over year, while homes sold have climbed more than a quarter over the same period. Pending sales have jumped over 40 percent from a year ago, signaling strong contract flow even as buyers take their time.

Pricing is reacting to this mix of demand and supply in interesting ways. The typical home value is up about 25 percent year over year, and the median list price has risen by a similar rate, yet the average sale-to-list ratio sits just under 100 percent.

Homes are spending more time on the market than a year ago, with the median days on market rising to the high 70s in this rolling three-month view. Months of supply is close to six, higher than the wider Chicago market’s roughly three months of supply, even though Woodlawn is still characterized as a seller’s market. A little more than one in four sales close above the asking price, and that share is higher than it was last year, underscoring that well-priced homes still attract strong offers. Whether you are a buyer trying to navigate these shifting dynamics or a seller aiming to price confidently, Agent Pronto can connect you with an agent who knows how to work this market.



Learn more about what Woodlawn has to offer.

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.

Find your Woodlawn real estate agent today →


Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“We had such a great experience working with Victoria and Sam! They were always quick to respond whenever we sent a home we were interested in or had questions. They were willing to go on as many tours as it took to help us find the right fit and were honest about steering us away from homes with structural concerns. It was clear they genuinely had our best interests at heart and wanted us to find a home we’d love. They’re also both funny and easy to get along with, which made the entire process that much more enjoyable. We couldn’t recommend them enough!”

Caden Burgess · Wilmington, IL

Photo of Victoria Holmes
Berkshire Hathaway HomeServices Chicago
“Kim Wirtz A fantastic sales person,Thank you very much for selling my property in such a short time.”

Tracy Lin · Midlothian, IL

Photo of Kim Wirtz
Wirtz Real Estate Group, Inc.
“I highly recommend working with Meldina! She is incredibly accommodating and always willing to show the properties, even on the short notice. She is very knowledgeable about the location we are exploring and her positive attitude, amazing energy and solution oriented mindset truly make a difference.Her professionalism and enthusiasm make the entire experience enjoyable. Thank you, Meldina, for you outstanding support and dedication.”

Alma A · Skokie, IL

Photo of Meldina Realty Group
Century 21 Dream Homes
“Jose made the process incredibly smooth is first-time buyers.”

Fernando · Joliet, IL

Photo of Jose Alarcon
Realty of America
“Selling our first home was emotional, and we couldn’t have asked for a better realtor than Brittany. When our first offer fell through, she had us under contract with a second offer within 24 hours! Her unwavering confidence and steady reassurance helped us feel at ease during such an uncertain time, especially as first-time sellers. Brittany supported us every step of the way, always making time to listen, answer our questions, and talk through our concerns. We felt heard, cared for, and confident that she had our best interests at heart. This was our second real estate transaction with Brittany, and we would never work with anyone else. We’re so grateful for her dedication, expertise, and kindness. We cannot recommend her highly enough!”

Vanessa Peters · Lombard, IL

Photo of Brittany Simon
Compass
“Renee was very helpful in our search for a house. She was very friendly, knowledgeable and very easy going personality. She and her office assistant were always available if there were any questions”

Angela Diaz · Arlington Heights, IL

Photo of Renee OBrien Group
Keller Williams North Shore West
“I can’t say enough wonderful things about Steve Goodman and the experience we’ve had working with him over the past 10 years. Steve was my realtor when I purchased my very first condo, and 10 years later, he was right there with us as we sold that condo and purchased what we hope will be our forever home. Having the opportunity to work with the same realtor through such an important chapter of our lives speaks volumes about the trust and confidence we have in him. What sets Steve apart is that he genuinely puts his clients’ best interests first. He is never pushy or focused on simply making a sale. Instead, he takes the time to listen, answer every question, offer honest advice, and make sure you feel comfortable with every decision. He is incredibly patient, knowledgeable, and always willing to go the extra mile.”

Joanna · Des Plaines, IL

Photo of Steven Goodman
RE/MAX Suburban
“Was impressed from the beginning when the owner answered the phone and made an appointment within a day or two to come out to the property. When we decided to put the house on the market, they were extremely professional And answered all our questions. The photographer came out promptly, and took amazing pictures of the property. It was listed the next day,and our house sold in less than a week. Andrew McCatty was our broker. He could not have been more knowledgeable or professional. Any questions that we had, Andrew either answered the phone or got back to us very quickly. Highly recommend Andrew and Century 21 Circle. Would only work with them again and would recommend them to family and friends.”

Debbie · Burnham, IL

Photo of McCatty Real Estate
Century 21 Circle
“Jeff is a knowledgeable professional. Trustworthy who will give you excellent feedback and advice”

Vin Peseski · Naperville, IL

Photo of Jeff Coros Team
Century 21 Affiliated
“Barb was a pleasure to work with, and I would highly recommend her to anyone.”

George Stell · Minooka, IL

Photo of Barb Gall
RE/MAX Remax Ultimate Professionals
“We were referred to Tracy in our move from downtown to the suburbs, and we couldn’t have asked for a better experience. She made what can be a stressful process feel easy and manageable from start to finish. Tracy was both professional and personal, detail-oriented, responsive, and always quick to act when it mattered. Her deep knowledge of the local market and strong connections were invaluable throughout our purchase. We would wholeheartedly recommend Tracy to anyone looking to buy a home!”

The Claussen Family · Hinsdale, IL

Photo of Tracy Anderson
Compass
“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.”

John MacRitchie · Chicago, IL

Photo of The Jones Group
Berkshire Hathaway HomeServices
“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.”

Job Ojo · Plainfield, IL

Photo of Rose Riordan
Century 21 Affiliated
“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!”

Merim Vilic · Des Plaines, IL

Photo of Emir Vulic
Owners.com
“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!”

Luke Turck · Chicago, IL

Photo of Paula Calzolari
Berkshire Hathaway Starck Real Estate
“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.”

Tiffany · Chicago, IL

Photo of Jeff Phillips
Berkshire Hathaway Home Services Chicago
“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.”

Dan Coglianese · Orland Park, IL

Photo of Househunters4u Team
Berkshire Hathaway Chicago
“Melissa Young is an excellent realtor. I highly recommend her.”

Michael Withers · Chicago, IL

Photo of Melissa Young
Berkshire Hathaway Home Services Chicago
“Working with Bryce was a fantastic experience! He is professional, knowledgeable and went above and beyond at every step of the process. He took the time to truly understand what I was looking for in a new home and he expertly negotiated on my behalf. I would highly recommend Bryce to anyone who is looking for a dedicated real estate agent who has your best interest.”

Katie · Oak Lawn, IL

Photo of Bryce Buck
Elevate - The Real Estate Company
“Laura is Amazing!”

Stephen Brady · Chicago, IL

Photo of Topp team
Berkshire Hathaway Homeservices

Frequently Asked Questions

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.


Looking for an agent in a different Chicago neighborhood?

We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.