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.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
Information and statistics on the latest trends in the Oakland real estate market. *
Jun 1, 2026 - Aug 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 (Jun 2026 - Aug 2026).
Oakland currently leans toward sellers, with a seller’s market gauge reading of 32 and only 2.4 months of supply in this rolling three-month view. Active listings are down about a quarter from a year ago, limiting choices for buyers. At the same time, the typical home value is up roughly 9 percent year over year, signaling steady price appreciation despite softer listing activity.
Looking more closely at demand, homes sold have surged by about 175 percent compared with this time last year, even as new listings fell by more than half. This mix of stronger sales and fewer fresh options helps explain why supply has tightened and supports prices in the neighborhood.
Buyers still see some breathing room, with a median of 85 days on market and an average sale-to-list ratio just under 98 percent, close to the broader Chicago area. Only about one in four homes sold above list over the period, down slightly from last year, which can create negotiation opportunities for well-prepared purchasers. Compared with Chicago overall, Oakland’s prices are a bit lower while its supply is slightly leaner, keeping conditions tilted to sellers but not overheated. Both buyers and sellers can benefit from an expert guide in this environment, and Agent Pronto can connect them with a local agent who understands these trends.
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.
“Kim helped us sell our home, and I can’t recommend her enough. She answered my questions late on a Friday and even on a Sunday during a holiday weekend. She was always available when we needed her. In a market where every offer deserved a close look, she helped us sort through them and choose the best one. We’re grateful for her hard work and guidance.”
“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.”
“Renee treats customers professionally and at the same time as friends. She goes above and beyond what is required on all facits of the process. She makes the process, which appears to be a mountain to climb, a pleasureable, simple process. I would unequivocally recommend Renee to anyone looking for a 'Best in the business' agent. Mark Stephens”
“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.”
“Jeff is a knowledgeable professional. Trustworthy who will give you excellent feedback and advice”
“Barb was a pleasure to work with, and I would highly recommend her to anyone.”
“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!”
“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.”
“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.”
“Laura is Amazing!”
“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.”
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.
We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.