- Agent Pronto
- Florida
- Winter Haven
- 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.
Compare the top 25 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 May 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.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
Home buyers and sellers love Agent Pronto.
Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.
“Cheryl is a very knowledgeable and professional realtor. If I have to do this again, she will be my first choice. It was amazing that after our first showing she quickly realized the type of neighborhood I want to look at, so we wasted no time.”
“The agent recommended by Agent Pronto sold the house in two days.”
“Our agent, Tammy Graham, has been wonderful! We are relocating 13 hours away, she went above and beyond for us. We are very grateful to all involved.”
“Rachel was very supportive in helping me sell my home. She never gave up until she got me the right price. She is a very good salesperson! ”
“Extremely helpful and attentive to our issues and needs. Went above and beyond to be sure we had a stress-free experience! ”
“Quick response, great connection options. Cassandra was an excellent choice for us. She responded promptly to any of our questions, was honest from the beginning and, kept us up to date with the process. Cassandra made it very easy for us. We felt like we were her only buyers/clients.”
“After deciding on relocating to Central Florida from Utah, we reached out to a few different realtors. Kevin stuck out to us as he was able to really lay out our options. We are so thankful and appreciative to work with Kevin. After deciding on a new build, he kept us posted on the progress, he was knowledgeable and always on top of things. It was certainly a relief to see how much he cared and looked out for our best interest considering we were 2800 miles away. We would definitely use Kevin again as our realtor and certainly would recommend his services.”
“Fabio was very professional, open, transparent, and reliable throughout the entire process. He really cared about us, understood our entire needs... Best realtor I've ever met.”
“The contact with William was perfect. He was professional and friendly, and helped me to make my purchase without any problems—even well past closing he was willing to assist with admin issues.”
“My experience with Deepak Team was above and beyond what I expected. Great team to work with.”
Downtown Winter Haven real estate Market Report.
Information and statistics on the latest trends in the Downtown Winter Haven real estate market, updated for May 2025. *
The typical home value in Downtown Winter Haven is projected to be $286,760 for the month of May. April’s finalized data reported the typical value of a home in the neighborhood to be $296,800—up 26.84% over the previous 12 months. For comparison, city-level data pegged home values at $282,350 in Winter Haven for the most recent reporting period. That number is expected to float around $275,020 in May.
Downtown Winter Haven had 12 new listings and 10 listings that went under contract in April, increasing the area’s total available inventory to 17—up 13.33% from the previous month. Inventory is projected to have further increased in May.
The median listing price for homes in Downtown Winter Haven grew 7.43% from March to April, bringing the current median listing price to $267,500. Based on projected data for May, 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 April 2025, the median time for a listed property to go pending was 74.5 days, compared to 118 days in April 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 May.
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 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.
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!
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!
Resources for buyers and sellers.
Tips and market insights to make your Winter Haven real estate journey a success.
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. 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.
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