Buy an Oakland, FL home with the perfect real estate agent

We analyze top real estate agents in Oakland and across the country to find you the most proven local agents, for free.

Oakland, FL real estate

Compare the top real estate agents in Oakland

Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 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.

The easiest way to find the best real estate agent.

Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.

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Oakland real estate Market Report.

Information and statistics on the latest trends in the Oakland real estate market, updated for August 2025. *

The typical home value in Oakland is projected to be $627,000 for the month of July. June’s finalized data reported the typical value of a home in the city to be $648,000—down 7.43% over the previous 12 months. For comparison, county-level data pegged home values at $435,000 in Orange County for the most recent reporting period. That number is expected to float around $430,000 in July.

Oakland had 14 new listings and 12 listings that went under contract in June, increasing the area’s total available inventory to 31—up 3.33% from the previous month. Inventory is projected to have further increased in July.

Of those 31 active listings, 38.71% reduced their price in the month of June. The median listing price for homes in Oakland fell 11.39% from May to June, bringing the current median listing price to $575,000. Based on projected data for July, listing prices may continue to fall.

The number of days that homes have been on the market prior to going under contract rose year-over-year. In June 2025, the median time for a listed property to go pending was 18 days, compared to 1 days in June 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this July.

Oakland, FL real estate
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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.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Oakland has to offer.

Oakland offers residents a charming blend of scenic natural beauty, vibrant community events, and a welcoming small-town atmosphere that enriches everyday life.

Oakland offers a peaceful retreat with a genuine sense of community that sets it apart in the heart of Orange County. Nature is never far away, as the town is bordered by lush conservation land and the scenic West Orange Trail, where locals jog, cycle, and connect with the beauty of Florida’s outdoors. Waterfront views abound at Oakland Nature Preserve, a hidden gem with walking trails, boardwalks, and interactive environmental programs perfect for families and nature enthusiasts.

The spirit of the town is enlivened by regular gatherings at Speer Park, which boasts playgrounds, tennis courts, and shaded picnic areas. For families considering a move, educational opportunities are impressive—Oakland Avenue Charter School stands apart for its personalized approach and community engagement. Nearby, residents can easily access the shopping, dining, and entertainment found in Winter Garden, while remaining insulated from the busyness of larger urban centers.

Local events, such as farmer’s markets and seasonal celebrations, foster a sense of belonging and make it easy to form new connections. Whether you’re captivated by small-town charm or searching for a serene place to call home, Oakland delivers a blend of tranquility, recreation, and convenience. Should you be ready to explore the possibilities of buying or selling a home here, Agent Pronto is ready to match you with knowledgeable real estate professionals dedicated to making your move seamless.

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Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!

Sarah W.

Take the guesswork out of finding an agent.

With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.

We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Oakland to qualify the best agents for your specific needs.

We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.

Data analysis with a human touch.

Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Oakland. But we don’t stop there.

Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.

Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!


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. 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.