We analyze thousands of real estate agents in Chicago’s Oakland 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 September 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 Oakland real estate market. *
May 1, 2026 - Jul 31, 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 (May 2026 - Jul 2026).
Oakland currently leans toward sellers, with the market gauge reading as a seller’s market. Months of supply sit at 3.2 in the latest rolling three-month view, a bit higher than Chicago’s 2.7 but still below the levels seen a year ago. A relatively low number of active listings, at just 17, helps keep conditions tilted in favor of those listing their homes.
Over the past year, prices have softened even as listing ambitions have risen. The typical home value is down about 8% year over year, while the median list price has jumped by roughly 44%, showing that sellers are testing higher price points. Sales activity has strengthened, with homes sold up more than 260% compared with the same rolling period last year and pending sales up about 77%, even though new listings have been cut by about half.
Homes are taking longer to sell, with the median days on market rising sharply to around 80 days in the latest data, and only about 14% of recent sales closing above list price as the average sale-to-list ratio hovers just under 100%. This combination of rising list prices, slower market times, and stronger sales volume signals a more nuanced market where pricing strategy really matters. Agent Pronto can connect both buyers and sellers with an Oakland agent who understands these dynamics and can guide them through each step.
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.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“The extra support and help Mike stepped up to do with us moving out of state prior to the house selling was outstanding. Mike stepped in to help with items requiring attention with the house that my wife and I couldn't do being out of state.”
“Barb was a pleasure to work with, and I would highly recommend her to anyone.”
“Jeff was super professional and knew his stuff through our whole house-selling process. Everything went smoothly and quickly. I highly recommend Jeff he's top-notch and has a great personality too.”
“Kim is very thorough and did an excellent job in marketing my property.”
“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!”
“Renee is a true professional! She helped us through the complicated process of selling our home while we were out of state. She was always available in a timely manner to answer all our questions and concerns, even through our separate time zones. She was also always helpful in finding us any connections we needed from landscapers, home cleaning, and HVAC services. We 1000% would recommend her to anyone who needs help buying or selling a home.”
“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.”
“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!”
“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!”
“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!”
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.
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 Oakland Realtor® or real estate agent today.
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