“Kim was excellent, answered all my calls or texts promptly! If it was not part of her job she advised me who to contact ! Absolutely the Best”
Wirtz Real Estate Group, Inc.
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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.
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 July 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
Mar 1, 2026 - May 31, 2026
Median sale price
$301K
+2.7%
from
Q1 '26
Median list price
$419K
+21%
from
Q1 '26
Active listings
21
-8.7%
from
Q1 '26
Homes sold
11
-8.3%
from
Q1 '26
New pendings
13
No change
from
Q1 '26
New listings
10
No change
from
Q1 '26
Quarterly Pricing Trends for Oakland
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Oakland
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Oakland
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Oakland
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Oakland
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Oakland
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
16
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Oakland currently leans toward sellers, with the market gauge signaling a seller’s market. Inventory sits at about three and a half months of supply, only slightly higher than the broader Chicago area. Homes are typically selling for a little over list price on average, reflecting solid demand.
Over the latest rolling three-month period ending in May 2026, prices and activity show a mix of shifts. The typical home value is down sharply year over year, yet the median list price has climbed strongly over the same time, suggesting sellers are testing higher price points while buyers find more value in closed deals. Sales activity has picked up compared with a year ago, with homes sold up by more than 40 percent and pending sales rising by a similar margin.
Homes are taking much longer to go under contract than a year ago, with median days on market surging, even as more than a third of recent sales closed above list price and the sale-to-list ratio has edged higher. Active listings are slightly higher than last year while new listings have slipped, which helps keep conditions tilted toward sellers despite the slower pace. With these crosscurrents in prices, timing, and competition, both buyers and sellers in Oakland can benefit from Agent Pronto’s help in finding an agent who understands the local dynamics.
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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“Excellent working with Mike McCatty highly recommend him and his services,thanks again Mike McCatty.”
Century 21 Circle
“Originally we were referred by our first lender and we could not have been more fortunate to work with Vicky and Sam. They were professional and realistic regarding our home search. We had not purchased a home in a very long time and Vicky was patient and understanding and was so attentive. avidly referred us to our second lender (the first was not communicative) and it was wonderful. Overall the whole experience was great! Thank you for helping us find our dream home!”
Berkshire Hathaway HomeServices Chicago
“Laura is Amazing!”
Berkshire Hathaway Homeservices
“Working with Tracy to buy our home was a great experience and she was always available and communicative even as we navigated some difficult parts of the negotiation with the seller. She was personally at every visit and even at the inspection and closing, going way above and beyond my expectations and previous experiences with buying agents. Thanks to her we found a home for our family and while we don't plan to buy in the near future I'd be happy to work with her again and again. Thanks Tracy!”
Compass
“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”
RE/MAX Suburban
“Meldina is an expert in the local market and an exceptional negotiator. Her professionalism, communication, and dedication exceeded our expectations. We highly recommend her!”
Century 21 Dream Homes
“Barb was 1/20 realtors who was willing to work with me in the beginning over 9 years ago. This is when I first purchased my home. I was cheap buyer. It went without saying I was going to be using her for the sale of the home 9 years later. She handled the hurdles flawlessly and talked me through and coached me the entire way. To say I appreciate her is an understatement. I sold my home after we relocated it of state and she coordinated every logistic of that sale on my behalf to he best of her ability. I recommend her without fail and would point every person in her direction that has a need for a solid realtor.”
RE/MAX Remax Ultimate Professionals
“Kathy fought a lot of uphill battles for us and despite hurdles at every turn (with prospective buyer) she pushed on and was able to secure our sale. I can't thank her enough for the amount of work she put in.”
Berkshire Hathaway Chicago
“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.”
Century 21 Affiliated
“Brittany is an AMAZING realtor and I don't say that lightly. She goes above and beyond to make sure that we are getting everything that we asked for and more. If you are looking for a realtor that goes out of her way to make sure her clients needs are met, you have found your realtor! I could not put into words how happy I am!”
Compass
“Working with Emir is always a pleasure. He was very helpful in coordinating work on our house for sale, working with vendors and providing valuable feedback on neccesary work vs. potential work items unlikely to generate return. We closed sale of house 3 weeks from time of first listing. I'd worked with Emir before and hope to do so again in the future.”
Owners.com
“Melissa Young was incredibly attentive and knowledgeable which was critical for me as a first-time home buyer. She helped me win my very first bid with a strong offer and guided me through challenges with the appraisal process. She sets the bar high and I am so happy with my beautiful first home in Chicago!”
Berkshire Hathaway Home Services Chicago
“Great experience! Very attentive, honest, and dedicated. Professional, efficient, and easy to work with. Highly recommended!”
Century 21 Affiliated
“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.”
Century 21 Realty Associates
“Shawn is a perfect example of everything a new homeowner could want in a realtor. He's patient, informative and passionate about helping you find the right home. Shawn goes the extra mile in preparing detailed documents on every listing you visit and has a vast knowledge of property pros and cons. You also know you'll get a honest and trustworthy professional at your side when you work with him. I can't recommend Shawn enough!”
Berkshire Hathaway HomeServices
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”
REALTY OF AMERICA
“Renee O'Brien was very understanding, helpful, and kind .... knowledgable in the house situation and problem solving to move the sale along swiftly...”
Keller Williams North Shore West
“Before using Jeffry as my agent, I had looked at several homes with 3 other agents for almost a year. Within 2 months of working with Jeffry, we found the home that I had been looking for and was the perfect fit.”
Berkshire Hathaway Home Services Chicago
“John Campobasso was great to work with in selling our unit. He was professional, knowledgeable, and guided us through every step of the process. We really appreciated how upfront and straightforward he was. He always gave us honest feedback and clear expectations. He made the whole experience feel smooth and much less stressful than we anticipated. We’re so glad we worked with him and would definitely recommend his services to anyone looking to buy or sell.”
Keller Williams Thrive Realty
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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