“We can't recommend Brittany enough. She was extremely personable, patient, and a clear communicator from day one which was as honestly years ago when we thought we were moving...then didn't...then did. Her knowledge of the western suburbs is awesome, especially when it comes to crucial inspection details. We would have never even thought to ask about radon checks or sewer scopes (as well as warning about things like oil drums in crawl spaces) but she guided us through it all and made sure we were completely protected. Unlike other realtors we’ve worked with in the past, she truly fought for us every step of the way while being so understanding of our specific needs. Highly recommend Brittany and so happy we chose her.”
- Agent Pronto
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- Oakland
The best way to find top real estate agents in Oakland, Chicago, IL
We analyze thousands of real estate agents in Chicago’s Oakland neighborhood and nationwide to find you proven local professionals, for free.
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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 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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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
Quarterly Pricing Trends for Oakland
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Oakland
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Oakland
Rolling three-month data ending on quarter boundaries when available.
Quarterly Inventory and Sales Activity for Oakland
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Oakland
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Oakland
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 (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.
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“Renee is an incredibly knowledgeable agent that has a lot of experience, cares about her clients, and is trustworthy !! She knows the ins and outs of current real estate markets and how to strategically price a property so that it will sell in a timely manner but with the highest yield!! She has sold two of our properties over the last eight years (one in Illinois and one in Wisconsin) and we received more than we expected on each of the sales!! We cannot recommend her highly enough! Thank you so much, Renee!!”
“Daniel had helped us in the past with the purchase of our first home so it was an easy decision when we decided it was time to move again to use him. He was accommodating, helpful and gave insight when we were looking for a new house in a new area. He listened to our wants and pointed things out we may not have noticed ourselves. This time we used Daniel for the sale of our condo and the purchase of our new home and was attentive, engaged & made both the purchase and sale happen seamlessly. I highly recommend Daniel to anyone selling or buying! With him you will find someone who genuinely wants to help with the difficult process of buying / selling.”
“We had a great experience working with Giovanni to sell our home in Chicago. He was knowledgeable, responsive, and incredibly helpful throughout the entire process. He made everything feel smooth and stress-free, from preparing our home for the market to closing the sale. We always felt like we were in good hands and couldn’t be happier with the outcome. We would highly recommend Giovanni to anyone looking to buy or sell a home!”
“Nancy Cirje was absolutely wonderful to work with! She was friendly, professional, responsive, and made the entire process feel easy and stress-free. Nancy was always available when I had questions and truly went above and beyond to make sure everything went smoothly. I really appreciated her knowledge, attention to detail, and the personal care she brought to the experience. I would highly recommend Nancy to anyone looking for a listing agent who genuinely cares about her clients!”
“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.”
“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!”
“I cannot say enough good things about my Brooke experience. Her knowledge of the overall market and in particular my building was just amazing. Brooke made the entire process stress free I promise. She is kind, funny, engaged and tough all at the same time. She negotiated a wonderful deal for me and I could not be happier with the experience.”
“Nicole and team could not have been better. List to close in under two months, with some challenging market conditions near us. Combine that with multiple offers, and 100% of ask and we couldn't be happier. She is thorough, meticulous, and kept us looped in to her thought process on marketing, offers, and closing. She previously helped family members with their purchase, and they were very happy as well. Thanks Nicole.”
“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.”
“If we could give more than five stars, we would. Our realtor went above and beyond every step of the way, making what could have been a very stressful process feel manageable and seamless. Because we were out of town, we had to rely on him completely, and he exceeded every expectation. He worked patiently with our tenant, navigated a particularly difficult condo HOA with professionalism, and managed every detail with a calm, confident, and assertive approach that gave us complete peace of mind. He also took the time to explain current market conditions using real data, helping us make informed decisions rather than simply telling us what to do. His negotiation skills were outstanding and ultimately helped us secure a fantastic all-cash offer. As if that weren't enough, he even cleaned out our small storage area to help get everything ready for closing. That level of dedication and care is incredibly rare. We truly don't have the right words to express our gratitude. His integrity, expertise, and willingness to go the extra mile made all the difference. We are beyond grateful for everything he did for us and would recommend him without hesitation to anyone looking for an exceptional realtor.”
“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.”
“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.”
“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!”
“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’”
“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!”
“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!”
“We’d like take the time thank Team Newman for all efforts in helping us sell our condo in Chicago. Working with Scott, Michelle, and Katie was an absolute game-changer in selling our Chicago condo. From day one, they went far beyond what we expected, bringing not just deep market knowledge, but genuine dedication and care to every step of the process. They took the time to understand our goals, gave smart data-driven recommendations, and were always willing to share their advice at each step of the process. What really stood out was their willingness to go the extra mile. They made what could have been a stressful experience feel smooth and manageable. Thanks to their expertise and commitment, our condo sold quickly and at a fantastic price. We couldn’t be happier with the outcome and would wholeheartedly recommend them to anyone looking to buy or sell in Chicago. Truly a five-star experience from start to finish!”
“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.”
“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.”
Frequently Asked Questions
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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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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.
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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.
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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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