“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.”
Century 21 Affiliated
- Agent Pronto
- Florida
- Winter Haven
- Downtown Winter Haven
The best way to find top real estate agents in Downtown Winter Haven, Winter Haven, FL
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Compare top Downtown Winter Haven real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. 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.
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“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”
Century 21 Wolfs Crossing Realty
“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.”
Keller Williams Realty At The Lakes
“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!”
Keller Williams Advantage 2 Realty
“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.”
Century 21 Century21 Rosa Leon
“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!”
Darrell Durham, Licensed Real Estate Broker
“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!”
Keller Williams South Shore
“Extremely helpful and attentive to our issues and needs. Went above and beyond to be sure we had a stress-free experience! ”
Florida Realty Marketplace
“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.”
Elite Investors Reatly Luxury Real Estate
“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.”
Top Listing Group by eXp Realty
“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.”
eXp Realty, LLC
“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.”
Charles Rutenberg Realty Charles Rutenberg
“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.”
Coldwell Banker Residential Real Estate
“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”
Fathom Realty FL LLC
“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.”
SellState Centric Realty
“Excellent job”
Ocala Realty World
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 $170,000 for the month of October. September’s finalized data reported the typical value of a home in the neighborhood to be $185,000—up 15.63% over the previous 12 months. For comparison, city-level data pegged home values at $304,700 in Winter Haven for the most recent reporting period. That number is expected to float around $307,060 in October.
Downtown Winter Haven had 10 new listings and 10 listings that went under contract in September, decreasing the area’s total available inventory to 10—down 9.09% from the previous month. Inventory is projected to have further decreased in October.
The median listing price for homes in Downtown Winter Haven grew 26.71% from August to September, bringing the current median listing price to $226,500. Based on projected data for October, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract rose sharply year-over-year. In September 2025, the median time for a listed property to go pending was 37.5 days, compared to -2 days in September 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 October.
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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.
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.
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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