“There were issues going into buying our first home but Chandra made the process smooth, fast and was with us every step of the way. She got us the best possible deal & made sure on closing day we were taken care of. Absolutely love her!!”
- Agent Pronto
- Florida
- Oakland
The best way to find top real estate agents in Oakland, FL
We analyze thousands of real estate agents in Oakland 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 June 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
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 (Mar 2026 - May 2026).
Year-over-year, Oakland’s rolling three-month data shows mixed price trends, with the typical home value down notably even as list prices have climbed. At the same time, active listings have inched up compared with a year ago, suggesting buyers now see a bit more selection than they did previously.
Looking more closely at the latest three-month window through May 2026, the median list price has surged from earlier in the year while the typical home value has moved up more modestly. Homes are spending a median of just 11 days on the market, and nearly half go off-market within two weeks, reflecting that well-priced properties can still draw quick offers.
Inventory is sitting at about 3.1 months of supply, down from a year ago and aligning with Oakland’s classification as a seller’s market. With about 17 percent of recent sales closing above list price and the average sale-to-list ratio near 98 percent, pricing and negotiation strategies matter on both sides of the table, and Agent Pronto can connect buyers and sellers with a local agent who understands these dynamics.
Learn more about what Oakland has to offer.
Oakland offers residents a close-knit community with safe neighborhoods, plenty of green space, convenient local amenities, and easy access to nearby urban opportunities, all while preserving a relaxed, small-town feel.
Oakland offers small town scale with quick access to major job and entertainment centers. Positioned just west of Orlando, it sits near the Florida Turnpike and key commuter routes, which makes daily travel to downtown offices, hospitals, and universities practical while keeping home life quieter and more relaxed.
Residents enjoy a strong connection to the outdoors. The paved West Orange Trail runs through town, popular with cyclists, runners, and families out for an evening stroll. Waterfront parks along Lake Apopka, including Oakland Nature Preserve, provide boardwalks, birding platforms, and educational programs, adding an easy way to unwind close to home.
Daily needs are straightforward. Groceries, healthcare, and services cluster along nearby corridors into Winter Garden and Clermont, while local eateries such as Crooked Can Brewing Company in adjoining Plant Street Market and the Downtown Winter Garden district give residents dining and social options without a long drive. Families look closely at school options within Orange County Public Schools, as well as nearby charter and private campuses.
With growth bringing new neighborhoods and rising demand, having a local real estate expert can make a real difference. An agent who understands Oakland’s traffic patterns, school zones, and hidden pockets of value can simplify decisions, anticipate issues, and keep timelines on track. Agent Pronto connects both buyers and sellers with those professionals so the process feels less stressful and more manageable from first showing to closing.
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“Danny is great real estate agent you can trust and rely on”
“Mình được người quen giới thiệu Thắng và rất vui khi được làm việc cùng Thắng. Thắng rất tận tâm, vui vẻ, luôn lắng nghe nhu cầu của khách hàng và hỗ trợ rất nhiệt tình trong suốt quá trình tìm nhà. Không tạo áp lực, luôn tư vấn rõ ràng để mình có thể đưa ra quyết định phù hợp. Nếu bạn đang tìm realtor nói tiếng Việt được tại Orlando, mình rất recommend Thắng”
“She listened and understood what was needed/wanted. She was aggressive with offers and getting compensations. Would use her again.”
“David Dorman has sold my husband all of his previous homes and sold them as he moved and upgraded as well. Even so I wanted David to map out his strategy for selling my rental property home. He valued it correctly, promoted it quickly, got significant views and offers and held on until he negotiated the right deal. He knew how to not spend time off market with buyers who wouldn't complete the deal and steered me in the right directions. The home sold much faster than expected for what I was hoping to get. David gives each client the same world class service whether you Home range is $200K or Millions. Thank you David and Century 21 for making this process stress free.”
“10/10 realtor for new construction! We built a home with KB Home over in Weeki Wachee Florida, and we had heard how important it was to have a realtor who understood inspections. We hired Rich because this is where he specializes, and he did not disappoint. He was truly with us every step of the way and guided us not only through hiring inspectors, but educated us on what to look for when noticing potential problems. Rich is a wealth of knowledge and won’t ever leave you hanging. In fact, I don’t think I have ever seen a realtor as passionate and invested in the process. This guy will look out for you. Another great part, as a buyer, his services are free to you because the builder pays him all of his commission. It is honestly just silly not to have him by your side for guidance and support. He may also make you laugh from time to time. 😅 Thank you for everything you did for us and helping us build our dream new construction home in the Tampa Bay area!”
“Al Spry can assist you whether you're planning to purchase or sell a property. He has a deep knowledge of the area and offers great ideas and recommendations. He's a great listener which proved valuable while narrowing down the many options and decisions faced. I highly recommend Al Spry for all your real estate transactions.”
“Paula was absolutely wonderful to work with. She was always available to answer questions and helped me through the whole process. I highly recommend her!”
“Zachary Greenberg was the correct choice. He was knowledgeable, he communicated as the process evoleved. His whole staff was as well. I felt my interests were being met. Alex Paganucci”
“This is the 2nd time I've utilized Debra's services. She is very good at her job. She is knowledgeable, efficient, always available and cares about the customer. I highly recommend her to anyone looking to buy or sell. Thanks, Debra!!”
“Cory did an excellent job from start to finish. He was professional, responsive, and made the entire process smooth and stress-free. I really appreciated his attention to detail and clear communication. Highly recommend working with him.”
“I have worked with Adry Narvaez before as in my prior review, I could not imagine a more committed, resposible, knowledgeable and personable person to work with. She is the best in her field. She has brought me to my dream hopm and for that reason I regret I might not need to work with her again, however I sm lucky to have gained and empathic and true friend.”
“We absolutely loved working with Madeleine! From day one, she was so friendly and easy to talk to. She was always available to answer our questions or set up a showing, no matter how many houses we wanted to see. Her knowledge and guidance made the whole process so much easier and less stressful. We always felt like she genuinely cared about helping us find the right home. Couldn’t have asked for a better realtor — highly recommend!”
“Erika was the key to getting this house sold. Without her help and experience the wonderful outome would not have been achieved. Erika was knowledgeable, professional, friendly and went above and beyond to help with this property sale. You would benefit from Erika's help on any property purchase or sale!”
“I feel that this world is a better place knowing that there are people like Mr. Milo Smith in it. He goes above and beyond the the call of duty, he is a hard worker and he makes himself available which means a lot in his type of business. Thank God for him! I know he will keep up the good work because he was that way from start to finish. I will tell everyone to get in touch with Milo.”
“Excellent experience”
“I had the pleasure of working with Claudia Garzón as my realtor, and I couldn't be more satisfied with her work. From the very beginning, she showed a high level of professionalism, responsibility, and an inspiring motivation that made the entire process much smoother and more manageable. Claudia has an exceptional ability to solve any issues that may arise, always finding quick and effective solutions. Her experience and dedication made a real difference at every stage of the transaction. I highly recommend her with complete confidence. Thank you, Claudia, for your outstanding work!”
“Patty is a pleasure to work with. Florida was not a market that I had experience with, but Patty's knowledge and expertise put me at ease from our first Zoom meeting. She is very personable, and has a great attention to detail which I really appreciate. Patty would go the extra mile to perform any research necessary to address my questions or concerns. It is no surprise she is a leader in her market. I would definitely look forward to work with Patty again.”
“Charles listened to all of our wants, showed us an amazing house that we instantly loved and was more helpful then we could have imagined”
“Sam sheen realty was FANTASTIC !! I COULDN'T HAVE ASKED FOR BETTER AGENTS”
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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