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Real estate in Chicago’s Oakland neighborhood.

Compare top Oakland 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.

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Oakland real estate Market Report.

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

Latest Rolling 3-Month Snapshot

Jul 1, 2026 - Sep 30, 2026

Median sale price
$360K
-15% from Q2 '26
Median list price
$351K
-17% from Q2 '26
Active listings
12
-37% from Q2 '26
Homes sold
5
-29% from Q2 '26
New pendings
2
-75% from Q2 '26
New listings
4
-56% from Q2 '26

Quarterly Pricing Trends for Oakland

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

Quarterly Pricing Trends for Oakland Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $385K Median sale price in Jan 2022 - Mar 2022: $300K Median sale price in Apr 2022 - Jun 2022: $395K Median sale price in Jul 2022 - Sep 2022: $395K Median sale price in Oct 2022 - Dec 2022: $333K Median sale price in Jan 2023 - Mar 2023: $294K Median sale price in Apr 2023 - Jun 2023: $302K Median sale price in Jul 2023 - Sep 2023: $418K Median sale price in Oct 2023 - Dec 2023: $387K Median sale price in Jan 2024 - Mar 2024: $337K Median sale price in Apr 2024 - Jun 2024: $385K Median sale price in Jul 2024 - Sep 2024: $247K Median sale price in Oct 2024 - Dec 2024: $363K Median sale price in Jan 2025 - Mar 2025: $345K Median sale price in Apr 2025 - Jun 2025: $493K Median sale price in Jul 2025 - Sep 2025: $315K Median sale price in Oct 2025 - Dec 2025: $386K Median sale price in Jan 2026 - Mar 2026: $293K Median sale price in Apr 2026 - Jun 2026: $425K Median sale price in Jul 2026 - Sep 2026: $360K Median list price in Oct 2021 - Dec 2021: $512K Median list price in Jan 2022 - Mar 2022: $399K Median list price in Apr 2022 - Jun 2022: $291K Median list price in Jul 2022 - Sep 2022: $299K Median list price in Oct 2022 - Dec 2022: $364K Median list price in Jan 2023 - Mar 2023: $300K Median list price in Apr 2023 - Jun 2023: $310K Median list price in Jul 2023 - Sep 2023: $415K Median list price in Oct 2023 - Dec 2023: $375K Median list price in Jan 2024 - Mar 2024: $275K Median list price in Apr 2024 - Jun 2024: $375K Median list price in Jul 2024 - Sep 2024: $320K Median list price in Oct 2024 - Dec 2024: $279K Median list price in Jan 2025 - Mar 2025: $335K Median list price in Apr 2025 - Jun 2025: $335K Median list price in Jul 2025 - Sep 2025: $360K Median list price in Oct 2025 - Dec 2025: $310K Median list price in Jan 2026 - Mar 2026: $347K Median list price in Apr 2026 - Jun 2026: $425K Median list price in Jul 2026 - Sep 2026: $351K Oct 2021 - Dec 2021 Median sale price $385K Median list price $512K Jan 2022 - Mar 2022 Median sale price $300K Median list price $399K Apr 2022 - Jun 2022 Median sale price $395K Median list price $291K Jul 2022 - Sep 2022 Median sale price $395K Median list price $299K Oct 2022 - Dec 2022 Median sale price $333K Median list price $364K Jan 2023 - Mar 2023 Median sale price $294K Median list price $300K Apr 2023 - Jun 2023 Median sale price $302K Median list price $310K Jul 2023 - Sep 2023 Median sale price $418K Median list price $415K Oct 2023 - Dec 2023 Median sale price $387K Median list price $375K Jan 2024 - Mar 2024 Median sale price $337K Median list price $275K Apr 2024 - Jun 2024 Median sale price $385K Median list price $375K Jul 2024 - Sep 2024 Median sale price $247K Median list price $320K Oct 2024 - Dec 2024 Median sale price $363K Median list price $279K Jan 2025 - Mar 2025 Median sale price $345K Median list price $335K Apr 2025 - Jun 2025 Median sale price $493K Median list price $335K Jul 2025 - Sep 2025 Median sale price $315K Median list price $360K Oct 2025 - Dec 2025 Median sale price $386K Median list price $310K Jan 2026 - Mar 2026 Median sale price $293K Median list price $347K Apr 2026 - Jun 2026 Median sale price $425K Median list price $425K Jul 2026 - Sep 2026 Median sale price $360K Median list price $351K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
60
Buyer’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).

Oakland currently leans toward buyers, with the local gauge at 60 indicating a buyer’s market in this rolling three-month view through September 2026. Homes are taking longer to sell, with the median days on market at 102, up 17 percent from a year ago. Supply sits at 3.9 months, similar to Chicago overall but much tighter than the high levels Oakland saw last year.

Prices have climbed compared with a year earlier even as activity has cooled. The typical home value is about $360,000, up more than 14 percent year over year, while the median list price has slipped slightly from last year, suggesting sellers are adjusting expectations. Sales volume is lighter, with homes sold down about 15 percent and new listings falling more than 70 percent year over year, which means fewer options but also less competition among sellers.

Buyer behavior has shifted as well, with roughly 40 percent of sales closing above list price in the latest period, a modest increase from last year despite the buyer-leaning conditions. At the same time, the average sale-to-list ratio has edged down to just under 97 percent, showing that many buyers are still negotiating some discount from asking prices. In this mixed environment of rising values, slower sales, and selective bidding, Agent Pronto can connect both buyers and sellers with an Oakland agent who understands the nuances of this market.



Learn more about what Oakland has to offer.

Oakland offers residents a welcoming, walkable community with green spaces, locally owned shops and eateries, engaging neighborhood events, and easy access to transit and everyday services.

Oakland offers a quieter, lakefront feel compared with nearby Kenwood and Bronzeville, with a strong sense of local pride and long-term residents. Stretching along the Lake Michigan shoreline, the neighborhood blends historic greystones, newer townhomes, and mid-rise condos, giving buyers a range of options close to downtown yet slightly removed from its pace.

Oakland’s identity is closely tied to green space and the water. Residents enjoy direct access to Oakwood/41st Street Beach and the Lakefront Trail, popular with runners, cyclists, and families. Ellis Park and the Ellis Park Arts & Recreation Center serve as anchors for community programs and youth sports. Nearby cultural and dining options in Hyde Park and The Loop add to the appeal, while the Chicago Transit Authority and major roads make commuting straightforward.

Local schools, such as Phillips Academy High School, and proximity to institutions like Bronzeville Classical and Kenwood Academy, support families looking to put down roots. Buyers are attracted to Oakland’s relative affordability along the lakefront, especially compared with Near North Side or Lincoln Park, while longtime owners watch values and reinvestment trends closely.

In a neighborhood where properties can move quickly and each block has its own character, timing and preparation are critical. Agent Pronto connects Oakland buyers and sellers with experienced local real estate agents who understand the community and can guide you confidently through your next move.

Find your Oakland 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 Oakland. 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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