“6:57 1 (24, .. . ★ Local Guide 3 days ago Whether you're selling a house or buying a house, it can be very stressful so having the right person on your side is very important and we are forever grateful for having Cassandra on our side and her closing team. They went above and beyond and always had our best interest first. Cassandra worked even while she was admitted at the hospital. She was amazing and was always attentive to how I was feeling even when she was not feeling well made sure we were always treated fairly And that things got done on time .we were well informed on all details at all times and felt confident that Cassandra was there to help us in any doubts or questions or concerns we had and helped resolve them we highly recommend her”
- 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 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 October 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.
We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent.
“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.”
“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!”
“Paula Mcconahay was very patient with us. She made sure that she was able to make time for us, even when we would keep adding houses to our list of possibles. Paula was very attentive to what we were looking for, and her input on the houses we looked at was extremely helpful. I could not be happier of Paula being reccommended to us.”
“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.”
“Best service out there! First time user and they are so responsive and professional! Truly appreciate Mr. Durham. He is the best of the best!!! We are in our beautiful home because of you! Thank you!”
“Kevin was very kind, listened, responded to all my questions, and got my house listed with beautiful pictures to show the beauty of my house. All went as smooth as possible!”
“Extremely helpful and attentive to our issues and needs. Went above and beyond to be sure we had a stress-free experience! ”
“Danny is by the far the best, he is very patient, knowledgeable, honest, and he truly takes care of the client no matter what. Thank you Danny so Much for what you do, and I will always conduct business in the future with you.”
“Very impressed by his professionalism and desire to help. Always available and attentive to answer any question l had in a clear and simple way.”
“Please see the previous comments. Tiffany is the best and truly world class! Tiffany was so wonderful to work with. She knew everything we needed and led us through a very unusual market with results beyond our expectations! We would not have trusted anyone else and she was gracious and kind even when we may not have been. We have referred our friends to work with her, she is the best. Grateful to her and the team.”
“Larry was more than a Real Estate Agent. He was more like a Family Friend. I am truly blessed and grateful to have worked with him. My home is everything I imagined it would be.”
“Very good service. We were in the Orlando area looking at homes and did not have a Realtor in the area that we were interested in. Agent Pronto hooked us up with a Realtor, Cheryl Brewer, the next day and we went out and found our home. Cheryl was very easy to work with and very knowledgeable in the realty business.”
“Working with Lakeia was a pleasure, she kept me informed every step on the way. She recommended a lender who not only provided great service but was able to close my VA loan in just only two weeks... If your thinking about buying or selling a home I would recommend Lakeia May with Century 21”
“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.”
“Excellent job”
Downtown Winter Haven real estate Market Report.
Information and statistics on the latest trends in the Downtown Winter Haven real estate market, updated for October 2025. *
The typical home value in Downtown Winter Haven is projected to be $222,500 for the month of September. August’s finalized data reported the typical value of a home in the neighborhood to be $215,000—down 36.58% over the previous 12 months. For comparison, city-level data pegged home values at $299,000 in Winter Haven for the most recent reporting period. That number is expected to float around $300,170 in September.
Downtown Winter Haven had 8 new listings and 9 listings that went under contract in August, decreasing the area’s total available inventory to 11—down 26.67% from the previous month. Inventory is projected to have further decreased in September.
The median listing price for homes in Downtown Winter Haven fell 5.3% from July to August, bringing the current median listing price to $178,750. Based on projected data for September, 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 August 2025, the median time for a listed property to go pending was 75.5 days, compared to 98 days in August 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 September.
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, walkable hub of dining, arts, parks, and community events, with convenient shops and a welcoming, neighborhood-focused atmosphere.
Downtown Winter Haven stands as the heart of Winter Haven, blending the energy of a growing city with a relaxed, lakeside spirit that draws residents and visitors alike. Strolling through this walkable district, you'll encounter winding brick-lined streets dotted with local favorites such as the historic Ritz Theatre and the inviting Central Park, which hosts vibrant community events year-round. Famed for its picturesque Chain of Lakes, this area offers easy access to scenic waterways and parks, making it a haven for outdoor enthusiasts and families who cherish an active lifestyle.
Cultural experiences abound, from the innovative exhibits at The Museum of Winter Haven History to live performances at Theatre Winter Haven. Foodies relish the eclectic mix of eateries lining Central Avenue, ranging from cozy coffee shops to chef-driven restaurants. When it comes to education, the Polk County Public Schools serve the neighborhood, with respected options like Winter Haven High School and Jewett School of the Arts nearby, making this neighborhood particularly appealing to families.
Downtown Winter Haven's close proximity to Lakeland and the rest of Polk County ensures both a tight-knit community feeling and straightforward access to regional amenities. Whether you're a first-time homebuyer dreaming of lakeside living or seeking a lively urban hub within a friendly atmosphere, Agent Pronto can seamlessly connect you with a skilled local real estate agent ready to guide you through every step of your Downtown Winter Haven journey.

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 covering the housing market in and around Downtown Winter Haven. 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 Downtown Winter Haven Realtor® or real estate agent today.
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