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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 November 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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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 →


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“Kim was a pleasure to work with. Great experience with Kim all the way around.”

Bill · Homer Glen, IL

Photo of Kim Wirtz
Wirtz Real Estate Group, Inc.
“Laura is hard working, dedicated, and responsive. She understood the challenges of a cash-only sale and made things happen that would have been dropped by less motivated realtors. As my listing agent she closed a sale on a property that was very difficult to sell at a sales price that other realtors balked at. She earned every penny of her commission. Hire her! You won’t regret it.”

chi761 ·

Photo of Laura Maressa
Kale Realty
“I highly recommend Jason as a realtor! He was professional, honest, trustworthy, and truly made the process of selling my home feel smooth and stress-free. He was always responsive, knowledgeable, and had my best interests in mind throughout the entire process. I felt confident knowing I was in good hands. Thank you, Jason, for your hard work and professionalism!”

arlinda cami ·

Photo of Jason Rosenberg
Infiniti Properties
“Selling our condo was a much smoother experience than I expected, and I truly have Larry to thank for that. From the very beginning, he was knowledgeable, responsive, and incredibly professional. Night or Day, weekday or weekend Larry answered the phone and communicated actively any information about the process to us. A true professional. He guided us through every step of the process, answered all of my questions, and always made us feel confident in the decisions we were making. What impressed me most was his negotiation skills. Larry advocated for our best interests every step of the way and worked hard to secure the best possible outcome. We always felt like he had our back and never settled for less than what our home was worth. If you’re looking for an agent who is honest, strategic, communicative, and genuinely invested in their clients, we can’t recommend Larry Lazar highly enough. Selling a home can be stressful, but he made the entire process seamless. We would absolutely work with him again and recommend him to anyone buying or selling a home.”

Karen Collins-Boddy ·

Photo of Larry Lazar
Charles Rutenberg Realty Charles Rutenberg
“Cannot emphasize enough how helpful Brad was during this whole process. We had literally zero idea about what we were doing and he helped in so many ways.”

mdoggie9 ·

Photo of Brad Magnant
Guidance Realty
“We drug him all over the city looking for the perfect home. Marc was with us every step of the way. He gave us solid advice and knew exactly what we were looking for. He made himself available morning, noon, and night for all of our questions.”

Paul O'Malley ·

Photo of Marc Dumas
Dream Town Real Estate
“Working with Henry and the Heart of Chicago Homes team was an incredible experience from start to finish. Throughout the entire process, I always felt supported, informed, and confident knowing he and the team had our best interests in mind. We were searching in one of the most competitive markets, and the townhome we fell in love with ended up receiving multiple offers. Although our offer wasn’t accepted initially, Henry stayed persistent and maintained consistent communication with the listing agent. Thanks to his dedication and follow-up, he was able to position us next in line and ultimately help us secure our dream home when the first deal fell through. Even though we originally had the second-best offer, his hard work, relationships, and determination made all the difference. We couldn’t be more grateful and would highly recommend Henry and his team to anyone looking to buy or sell a home!”

Brendan Chen ·

Photo of Jessica Macey
Real Broker LLC
“Walker was very responsive and would reply at most times of day quickly which was helpful as I work strange hours. Very knowledgeable. Thanks so much’”

wedes004 ·

Photo of Walker Robinson
RE/MAX Premier
“We cannot thank Mike and his team enough for their hard work. They are the definition of professional and were always one step ahead, keeping us informed every step of the way. They made what can usually be a stressful process feel incredibly easy and made the entire process seamless. They truly get things done. Highly recommend!”

zuser20170302083606206 ·

Photo of The Saladino Sells Team
Keller Williams ONEChicago
“I chose Helen because I knew I could count on her knowledge of the market as well as the neighborhoods of Chicago. She was incredibly knowledgeable throughout the entire process and always made me feel confident in her ability to address any questions or concerns I had. In fact, any question, concern, or issue that came up was addressed immediately. She was unbelievably responsive throughout the entire process. Purchasing a home can feel stressful and overwhelming at times, but Helen’s level of communication and follow through made all the difference. This is actually my second time using Helen as a realtor. A few years ago, she also sold a condo for me, and the confidence I had in her skills then was exactly why I contacted her again when I was looking for a new home. I would highly recommend Helen to anyone looking to purchase or sell a home!”

Jenna Klotz ·

Photo of Helen Sobel
Baird & Warner
“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.”

Liyuan Hu · Chicago, IL

Photo of Cinny Chui
Century 21 Realty Associates
“Jakeshia Thomas provided a great service. She helped us navigate a concurrent closing deal involving multiple real estate transactions, She repeated us, the buyers. She went above and beyond, making our real estate experience smooth and stress-free. Her level of professionalism and patience when working with first-time is unmatched. I can’t say enough positive things about her.”

Maria Moore ·

Photo of Jakeshia Thomas
Blue Door Dave Real Estate
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”

Bill Zabresky · Wheeling, IL

Photo of Lizette Andrews Delgado
REALTY OF AMERICA
“Reggie was amazing and so supportive through the whole process. He always took the time to explain anything that was confusing to me as a first time home buyer and he helped me find everyone else I needed to help me with the home buying process like a loan processor and attorney and everything. Highly recommend him to anyone and everyone!”

mdchevrier ·

Photo of Reginald Patterson
eXp Realty, LLC
“Kat was simply amazing! I was a first time buyer with a lot of gaps in my knowledge and she was super about answering my questions, responding to my last minute “wait what about..” moments and just educating me about what the expect. She is someone who clearly gets a lot out of helping folks find their perfect place and was always the first to ask the tough questions that I didn’t think to/know you could ask!”

ben ishibashi ·

Photo of Kathleen Collins
Nest Equity Realty
“Juan helped us immensely in buying our first home and answered every question we had. Would 100% recommend.”

Sara S. · Oak Park, IL

Photo of Juan Espinosa
E-Professionals Realty, LLC
“Thalia is an amazing realtor! 10/10! 5 stars! As a first time home buyer, I did not know what to expect or what the process of buying a home was. Thalia was amazing when she sat down with me and walked me through each and every step. She is extremely knowledgeable, and always available. I really appreciated her efficiency; Thalia works at the buyers pace, and when she says something will get done…..it gets done. She was always available to answer any and all of my questions….at anytime of the day! I am so happy Thalia was my realtor, and if I ever need to buy or sell a property, I will be calling Thalia back.”

Aleksandra Lemiesz ·

Photo of Thalia Mena
Coldwell Banker Realty
“Vergis did a great job helping us sell our home. We were very happy with the results of his hard work and would highly recommend his services! We thought his professionalism and attention to detail was very important to the process of selling our property.”

bahutson4 ·

Photo of Vergis Eiland
@properties Christie's International Real Estate
“Choosing Ruby Castelar was the best choice, she made the process smooth and stress-free. Ruby’s attention to every detail and commitment to finding the best place at the best price was exceptional!!”

Sanela Abdic ·

Photo of Lifestyle Home Transition Realty
Lifestyle Home Transition/Real Broker
“Absolutely thrilled with my experience working with Joey as my realtor! As a first-time homebuyer, I was feeling a bit overwhelmed, but Joey made the entire process smooth, clear, and stress-free. From the very first consultation, he took the time to understand my needs and preferences, offering valuable insights and expert guidance every step of the way. He was incredibly responsive, always available to answer questions or provide advice, and he went above and beyond to ensure I found the perfect home. His professionalism, knowledge of the market, and attention to detail truly set him apart. I couldn’t have asked for a better experience—Joey made what could have been a daunting process a breeze. Highly recommend him to anyone looking to buy or sell a home! 5 stars all the way!”

Jeremy Vera ·

Photo of Joey Diaz
PAK Home Realty

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.


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