“Very efficient, personable and professional. Went above and beyond to help sell the home.”

We analyze top real estate agents in Winter Haven and across the country to find you the most proven local agents, for free.
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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“Very efficient, personable and professional. Went above and beyond to help sell the home.”
“Cassandra was amazing to work with! We relocated from another state and that in itself is stressful but she made it easy with her detailed video walk-through and constant communication. She's professional, kind and incredibly organized. She even lent us her air mattresses so we could spend our first night in our new home comfortably before our moving truck arrived. Truly above and beyond throughout the entire process! We highly, highly recommend her!”
“I first reached out to David and Scott about selling our house two years before they actually listed it, and through that entire time David was always accessible to answer questions and address concerns that I had. David did a wonderful job selling our first house and we never considered using another agent when we sold our house in Winter Garden, and he did not disappoint. David and Scott are an excellent team and I would recommend them to anybody who wanted to have their house expertly listed and marketed”
“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.”
“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.”
“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!”
“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.”
“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.”
“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.”
“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.”
“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.”
“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!”
“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.”
“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.”
“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.”
“She did a great job, made selling very smooth.”
Information and statistics on the latest trends in the Winter Haven real estate market, updated for August 2025. *
The typical home value in Winter Haven is projected to be $304,990 for the month of August. July’s finalized data reported the typical value of a home in the city to be $296,660—down 1.0% over the previous 12 months. For comparison, county-level data pegged home values at $312,000 in Polk County for the most recent reporting period. That number is expected to float around $311,000 in August.
Winter Haven had 90 new listings and 110 listings that went under contract in July, decreasing the area’s total available inventory to 404—down 13.49% from the previous month. Inventory is projected to have further decreased in August.
Of those 404 active listings, 40.35% reduced their price in the month of July. The median listing price for homes in Winter Haven grew 8.51% from June to July, bringing the current median listing price to $325,000. Based on projected data for August, 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 July 2025, the median time for a listed property to go pending was 69 days, compared to 94 days in July 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 August.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
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.
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!
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.
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Tips and market insights to make your Winter Haven real estate journey a success.
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.
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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