“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
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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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“David is a great Broker/Agent. Always a pleasure to work with.”
Century 21 Carioti
“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
“Very efficient, personable and professional. Went above and beyond to help sell the home.”
Yellowfin 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
“Larry was by far the best realtor I've worked with. I've met with a few in the past and he takes the cake. He made looking for a house feel like a fun experience instead of a cut and dry transaction. And the number of resources he had at his fingertips. I had a question/inpection request, he knew a person. I was really impressed. I am always bragging about the team I had in getting me into my house, with Larry being the ring leader.”
eXp Realty
“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
“Christine was awesome to work with. She kept me totally up to date with the process. She was kind and pleasant adding a personal touch. I would totally recommend Christine to any one buying a home.”
Real Broker LLC
“We would like to commend Alan on the great job he did handling all the details and processes of our homebuying experience. He is a valuable representative to the Coldwell Banker name. Alan was attentive to our needs and took the stress out of purchasing a home. He was able to spell out in advance all of the details we would have to cover. He was always upbeat and had a tremendous attitude. I would highly reccomend him to anyone we know that is interested in buying a home in the state of Florida.”
Coldwell Banker 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
“We had a great experience with Leeroy. He is knowledgeable, attentive, and accommodating. He is also efficient, communicative, and understands our needs. Five stars for our agent, Leeroy. He made the whole process smooth and stress-free. I couldn't be happier. It was our blessing to work with him. Thank you.”
Dennis Realty & Investment Corp
“I had a very lovely experience buying my first home with agent Jose Meija. I recommend him for any future homebuyers. When we first met, he went out of his way to sit down and explain the process in detail to me. When I decided on a home, he was supportive through the lender and closing process, despite many hiccups along the way.”
Real Broker, LLC -- The Locals Team
“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
“Chaz and Chi Chi Tyler were very helpful and understood very well what we needed for our new home. They were able to find a great house for us in a matter of days. I would highly recommend them.”
Keller Williams Advantage Realty
“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
“We were SO fortunate to receive a call from Lottie Creech who responded to my inquiry on your site. Mrs. Creech is sweet, kind, knowledgeable and diligent. She guided us through a home search, connecting us with a very qualified home inspector resulting in our successfully purchasing a fabulous home with extensive grounds in the Lake Bernadette community. Anyone engaging Lottie Creech to assist them will be thankful they did.”
Future Home Realty
“She did a great job, made selling very smooth.”
Keller Williams Advantage III 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
Winter Haven real estate Market Report.
Information and statistics on the latest trends in the Winter Haven real estate market, updated for October 2025. *
The typical home value in Winter Haven is projected to be $307,060 for the month of October. September’s finalized data reported the typical value of a home in the city to be $304,700—up 1.57% over the previous 12 months. For comparison, county-level data pegged home values at $321,490 in Polk County for the most recent reporting period. That number is expected to float around $324,790 in October.
Winter Haven had 123 new listings and 97 listings that went under contract in September, decreasing the area’s total available inventory to 457—down 3.79% from the previous month. Inventory is projected to have further decreased in October.
Of those 457 active listings, 38.51% reduced their price in the month of September. The median listing price for homes in Winter Haven fell 5.17% from August to September, bringing the current median listing price to $311,830. Based on projected data for October, 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 September 2025, the median time for a listed property to go pending was 63 days, compared to 36 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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Seller’s Market
Buyer’s Market
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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 Winter Haven has to offer.
Winter Haven offers residents an active, lakeside lifestyle with plentiful recreation, a welcoming community, and convenient access to diverse dining, shopping, and cultural events.
Winter Haven turns everyday life into a lakeside ritual, with more than 50 waterways stitched together by canals for effortless boating, paddling, and sunset cruises. Families gravitate to the area for destination fun at LEGOLAND Florida Resort, while year-round recreation spans city boat ramps, waterfront parks, and the modern AdventHealth Fieldhouse & Conference Center. Culture thrives, too, with award-winning Theatre Winter Haven producing lively seasons and classes, and a downtown scene filled with local eateries, coffee roasters, and weekend markets. The city’s water-ski heritage lives on in festive shows and community regattas.
Education anchors the community. Polk County Public Schools supports neighborhood campuses and choice programs, and Polk State College’s Winter Haven campus offers affordable degrees, workforce training, and collegiate high school pathways that keep students on track close to home. Residents appreciate a range of housing options—from classic mid-century lakefront homes to new-build communities—plus quick access to services through the City of Winter Haven and a central location within Polk County. Whether you’re dreaming about a first home by the water or preparing to list, Agent Pronto can connect you with a trusted local agent who knows the currents of this market and can guide both buyers and sellers with confidence.
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 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 Winter Haven Realtor® or real estate agent today.
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