“Tracy was super helpful and extremely knowledgeable! Made our first time home-buying experience very comfortable!”
Howard Hanna Real Estate Services Howard Hanna
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The best way to find top real estate agents in Oakland, Middletown, OH
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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 2025. *
* 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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“Maura was truly amazing! We had been struggling selling the property for two months before she came on. Once we switched to Maura, we got an offer in <24 hours!! She did an amazing job keeping calm and collected during an incredibly stressful time!”
Coldwell Banker
“Christina was there helping us from start to finish. She did a great job of getting pictures for the listing. Getting feedback from prospective buyers. And handling all the paperwork that was involved along the way. We really appreciate how Christina looked out for our interest and got us to the "finish line" of selling our home!”
Fathom Realty Ohio
“Great resource beyond the sale!”
Comey & Shepherd Realtors
“Chad Shircliff was a great help in selling our mother's home after her move to retirement living. He was knowledgeable about the area and brought his expertise and advice throughout the entire process. With his help we sold the property quickly, for over asking, and with no hiccups along the way. I would definitely recommend him to family and friends and anyone needing a realtor.”
ERA Real Estate ERA Real Solutions Realty
“Love Kristy!!!!”
Coldwell Banker Realty
“Because we had to sell our property in a very short amount of time and remotely, it was crucial to find a real estate broker who was trustworthy, dependable, accessible and professional. Erin Young more than exceeded our expectations. She's also personable, thoughtful and caring. We believe we put our property in really good hands.”
Keller Williams Advisors Realty
“Everything went really fast.. was expecting about 2 months on market.... nope.. 2 days...and got more than expected .. very satisfied..”
Irongate Realtors
“Eli Price walked me through several struggles when negotiating and getting to the closing table. I would recommend him because of his communication skills.”
Coldwell Banker Realty
“Kristi is amazing and I could not recommend her more!”
eXp Realty
“Great job.....”
Coldwell Banker Realty
“Melissa was wonderful to work with and a true professional. We would highly recommend Melissa to everyone needing a really great gal and so much more. She will go out of her way to find you what you need in a home. We wish her continued success! ”
Star One Realtors
“Yuri was a friend of ours before my husband and I started house searching. Because of that relationship we decided to have Yuri represent us as we knew he would have our best interests at heart and would not try to sell us a house that wasn't a good fit for us. The whole process was fairly pain-free, and I attribute that to Yuri's clear and timely communication as well as the ease of access we had to him. Yuri's knowledge of the local house market and general house construction helped us find a house that is perfect for us!”
Plum Tree Realty
Oakland real estate Market Report.
Information and statistics on the latest trends in the Oakland real estate market, updated for November 2025. *
The typical home value in Oakland is projected to be $248,750 for the month of November. October’s finalized data reported the typical value of a home in the neighborhood to be $220,000—up 68.43% over the previous 12 months. For comparison, city-level data pegged home values at $229,450 in Middletown for the most recent reporting period. That number is expected to float around $239,800 in November.
Oakland had 2 new listings and 3 listings that went under contract in October, decreasing the area’s total available inventory to 1—down 50.0% from the previous month. Inventory is projected to have further decreased in November.
The median listing price for homes in Oakland grew 16.07% from September to October, bringing the current median listing price to $162,500. Based on projected data for November, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract has been fairly steady year-over-year. In October 2025, the median time for a listed property to go pending was 40 days, compared to 42 days in October 2024. However, in recent months the median number of days from listed to pending appears to be falling. That trend is predicted to have carried through to this November.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Oakland has to offer.
Oakland offers residents a welcoming, walkable community with convenient parks, local shops, and opportunities for active, connected living.
Oakland is a walkable pocket of Middletown where front porches, mature trees, and neighborly routines set the pace. Minutes from downtown, residents enjoy quick access to the Great Miami River and the paved trail network along the Great Miami Riverway, plus year-round recreation at city parks like Smith Park. City services are close at hand through the City of Middletown, while regional green spaces across Butler County add even more weekend options.
Families appreciate that Oakland is served by the Middletown City School District, with academic programs, athletics, and arts opportunities that keep students engaged from elementary through high school. Lifelong learners can continue just up the road at Miami University Regionals – Middletown, offering degrees, workforce training, and community events. Healthcare needs are covered by Atrium Medical Center, a full-service hospital with emergency care and specialty clinics.
On evenings and weekends, locals catch live performances at the historic Sorg Opera House, browse stacks and maker tools at the MidPointe Library System, or explore dining and small businesses in town and nearby Monroe. With a housing mix that ranges from early-20th-century bungalows to practical mid-century homes, Oakland offers approachable choices for first-time buyers and space for growing households.
Considering a move within Oakland—or preparing to sell? Agent Pronto can connect you with a top local real estate professional who knows the neighborhood and the broader market, making your next step clear and confident.
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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