1. Agent Pronto
  2. Florida
  3. Winter Haven
  4. Downtown Winter Haven

Find the perfect real estate agent in Downtown Winter Haven, Winter Haven, FL

We analyze top real estate agents in Winter Haven’s Downtown Winter Haven neighborhood and across the country to find you the most proven local agents, for free.

Real estate in Winter Haven’s Downtown Winter Haven neighborhood.

Compare the top real estate agents in Downtown Winter Haven

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.

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Downtown Winter Haven real estate Market Report.

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

The typical home value in Downtown Winter Haven is projected to be $205,540 for the month of July. June’s finalized data reported the typical value of a home in the neighborhood to be $215,000—down 13.83% over the previous 12 months. For comparison, city-level data pegged home values at $280,000 in Winter Haven for the most recent reporting period. That number is expected to float around $270,000 in July.

Downtown Winter Haven had 12 new listings and 9 listings that went under contract in June, increasing the area’s total available inventory to 17—up 13.33% from the previous month. Inventory is projected to have further increased in July.

The median listing price for homes in Downtown Winter Haven fell 9.81% from May to June, bringing the current median listing price to $239,000. 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 fell year-over-year. In June 2025, the median time for a listed property to go pending was 47 days, compared to 71 days in June 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this July.

Real estate in Winter Haven’s Downtown Winter Haven neighborhood.
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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 Downtown Winter Haven has to offer.

Downtown Winter Haven offers residents a vibrant blend of charming local shops, delectable dining options, and lively community events that foster a welcoming atmosphere.

Downtown Winter Haven offers a lively blend of historic charm and modern convenience, creating a true destination for those seeking community spirit in the heart of the city. The area’s tree-lined avenues are alive with local boutiques, eclectic restaurants, and galleries that make every stroll an inviting discovery. Residents and visitors can catch performances and exhibits at venues like the Ritz Theatre and the Winter Haven Public Library, while events at Central Park draw families and friends together throughout the year.

Education is at the forefront, with Winter Haven High School supporting a thriving academic and extra-curricular environment just minutes from the downtown core, complemented by Jewett School of the Arts for those seeking specialty programs. The neighborhood is a quick drive from Polk State College, ensuring access to higher learning for recent graduates and lifelong learners alike.

The scenic Chain of Lakes Trail connects downtown to the sparkling lakes that define the area’s landscape, inviting joggers, cyclists, and kayakers to stay active beneath Florida’s sunshine. Dining options span the globe, with beloved spots like Tempo 1930 and Richard’s Fine Coffees providing tasty fare in welcoming settings.

Centrally situated, Downtown Winter Haven is conveniently linked to Lakeland and Polk County, making it an excellent home base for work and leisure. Whether you’re settling down or preparing to sell, let Agent Pronto match you with a top local agent who understands the distinctive appeal of this thriving downtown neighborhood.

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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 Downtown Winter Haven 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 Winter Haven. 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.