“My wife and I are so happy to have chosen Cassandra as our realtor! This was our first home buying experience and we did not know where to begin. Right from the beginning, she explained how the process works and walked us through many homes based of our preferences. It did not matter to her how many homes we went through, she did not push us to make a decision and wanted us to continue until we found a home (in our case a model home in a new community) that we felt comfortable and right. When we finally selected our home, she was there every step of the way throughout the process (from the first contract being signed to design studio to pre dry wall and pre closing inspections to closing and everything else in between). She is just amazing! We felt as if we were her extended family with how much she cared for us and her communication was spot on, always got back to us when we had a question (in a reasonable time). She is truly an amazing woman and will fight for your dream home!”
- Agent Pronto
- Florida
- Oakland
The best way to find top real estate agents in Oakland, FL
Skip the search. We analyze thousands of real estate agents in Oakland and nationwide to find you proven local pros, 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 December 2025. *
16 recent sales
$205K-$1.17M price range
$450K median price
* 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.
The easiest way to find a top agent you can trust.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
- Tell us what you need.
- Answer a few quick questions about your real estate goals.
- Get matched.
- We’ll find your top local agents based on performance, expertise, and customer reviews.
- Connect and compare.
- Review your personalized recommendations and choose who’s right for you.
- Move forward with confidence.
- Whether you’re buying, selling, or both, you’ll have a proven expert on your side.
Trusted by over 500,000 buyers and sellers.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“David and Vicki were amazing to work with. They answered all our questions and requests promptly. They were honest and never pushy. David was amazingly quick to return calls and texts. Top notch customer service. We thoroughly enjoyed working with them and when we decide to upgrade we would love to work with them again.”
“Debra is a true Superstar! Not only did she help us find our forever home for retirement, she drove over an hour each way to get to the area we were looking at, and she did that several times over the course of two weeks for inspections and closing. Debra knows this business and is a true professional in every sense. Thank you so much for your hard work, and thank you for being our friend. (You too Dave 😁) Joel & Marlene”
“I had never worked with a realtor. And I continuously kept getting advice not to get a Realtor... because everyone put a money value on Realtors job. I am so glad I did Not listen to all those people!!! Getting a Realtor like Chasandra was the best decision I made when purchasing a home... I didn't feel any presure to choose the first home I saw... she is honest. Helpful, professional and above all she is looking out for your best interest in purchasing a home...she walks you threw the entire process....I was a pleasure having chasandra as my realtor and I will never forget her impact on my life ...”
“Once again Paula came through for us. She was always available for us whenever we needed her. Second home purchase for us with Paula, and once again she was on top of everything.”
“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!”
“Zach has been nothing but 100% professional. He answers all correspondence quickly and effectively. I must also say that his ability to get a deal finished is unparalleled. He truly has a gift with working in real estate.”
“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”
“Elsie was very knowledgeable, professional and worked with us with our best interest in mind. She facilitated all the process contacting the broker, inspectors, etc and kept us posted at all time. Working with her, instead of an agent trying to make a comission, we felt like a very close friend or a family member was taking care and looking after us. We have purchased multiple properties in the past and never had an experience even close to this one. She went out of her way to help us and we are very grafetul for that. Can't recommend Elsie high enough, expect excellence!”
“Daniel is an amazing person to work with. The level of communication and knowledge that he brings to the table everyday is top notch. I would recommend him to anyone looking to purchase a new home or sell their existing home. People say they care about their clients, Daniel shows this in his actions and commitment. It was a pleasure having the opportunity to work with him!”
“Deanna, thank you for staying the course. You had to re-center me a few times since I had family "stuff" happening simultaneously. I needed someone I could trust and I'm thankful that my friend recommended you.”
“Zac Hernandez was brilliant in the entier process and I cannot thank him enough. You are lucky to have him on the Keller Williams team. He guided me through every step of the way and was not only professional, but very kind and patient with me. Thank you, Zac!”
“Christine was awesome to work with. She kept me totally up to date with the process. She was kind and pleasant adding a personal touch. I would totally recommend Christine to any one buying a home.”
“Viewings and closure of offer was a very smooth experience with Karuna. Given the right inputs she set up all viewings without a hitch and we hit our planned viewings as per schedule agreed. She helped close my offer quickly. My experience with post closure paperwork was also smooth and on time as agreed.”
“Yandy Estrada was an excellent choice for us to help us buy our house, he helped and guided us every step of the way. Their trust and professionalism made every step of this adventure very easy. Definitely in our next investment I would choose Yandy Estrada and Rosa Leon again.”
“Great Experience!”
Oakland real estate Market Report.
Information and statistics on the latest trends in the Oakland real estate market, updated for December 2025. *
The typical home value in Oakland is projected to be $775,000 for the month of December. November’s finalized data reported the typical value of a home in the city to be $710,000—down 9.96% over the previous 12 months. For comparison, county-level data pegged home values at $440,000 in Orange County for the most recent reporting period. That number is expected to float around $439,510 in December.
Oakland had 8 new listings and 7 listings that went under contract in November, increasing the area’s total available inventory to 32—up 3.23% from the previous month. Inventory is projected to have further increased in December.
Of those 32 active listings, 18.75% reduced their price in the month of November. The median listing price for homes in Oakland grew 161.19% from October to November, bringing the current median listing price to $1,750,000. Based on projected data for December, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In November 2025, the median time for a listed property to go pending was 129 days, compared to 186 days in November 2024. In recent months the median number of days from listed to pending appears to be decreasing. That trend is predicted to have carried through to this December.
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, small-town atmosphere with plentiful green spaces and a convenient mix of local charm and easy access to nearby jobs, schools, and recreation.
Oakland offers lake views, shady streets, and an easy pace without sacrificing convenience. Along the southern edge of Lake Apopka, residents make the most of the outdoors on the West Orange Trail, a paved greenway perfect for morning rides and evening strolls, with access points just minutes away. Wildlife watching and quiet boardwalk walks are part of daily life at the Oakland Nature Preserve, a 128-acre sanctuary with a shoreline pier and hands-on environmental programs that connect all ages to the area’s ecology.
Families value education here, with the acclaimed Oakland Avenue Charter School serving elementary students and broader options available through Orange County. Community events, concerts, and exhibits at the Arts & Heritage Center add a cultural heartbeat, while Speer Park and local playgrounds keep weekends full. Everyday errands are simple, and dinner plans can range from food halls and breweries along Plant Street in nearby Winter Garden to lakeside dining spots a short drive away.
Commuters appreciate the straightforward access to Orlando, and recreation seekers find even more trailheads, golf, and freshwater fun toward Clermont. Housing spans classic bungalows and newer neighborhoods, with front porches and friendly sidewalks inviting conversation. Whether you’re upsizing, downsizing, or relocating for work or schools, Agent Pronto can connect you with a top local agent to help you buy or sell with confidence.
West Orange Trail • Oakland Nature Preserve • Oakland Avenue Charter School
Frequently Asked Questions
-
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.
Looking for an agent outside Oakland?
We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.