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We analyze top real estate agents in Winter Haven and across the country to find you the best veteran and military-friendly local agents, for free.

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Compare the top real estate agents in Winter Haven

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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Home buyers and sellers love Agent Pronto.

We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent.

“David was the perfect partner in selling our home in Clermont. From the moment I met him, I felt at ease and entrusted this important transation to him. He worked with me through various challenges as we prepared the home for sale and marketed the house perfectly. We accepted a full price offer just a day after it went on the market! As we navigated several buyer inspections, David communicated results and advised on next steps. As I had to travel out of the country for business as the sale concluded, he was crucial in helping me make buyer-requested repairs that resulted in less expense than the credit we were considering offering. David is funny and charming and made the entire experience pleasant. I highly recommend working with him!”

Sherrie Caltagirone · Clermont, FL

Photo of David Dorman
Century 21 Carioti
“There is not a more exceptional real estate agent than Cassandra. Anytime you needed advise or have a question she was always there to help. Communication on any question was just a phone call away. Always there to help you understand all issues of transaction without question. If you are looking for a real-estate agent there should be no hesitation on using Cassandra for all your real estate needs. Thank you Cassandra for a great experience.”

D · Kissimmee, FL

Photo of Cassandra Kelly
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.”

Martha DeBustamante · Wanaque, NJ

Photo of Patricia Hernandez
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.”

Liz Powers · St. Petersburg, FL

Photo of Larry Lanni
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!”

Jonathan Panciotti · Orlando, FL

Photo of Zac Hernandez
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.”

Susan A. · Haines City, FL

Photo of Christine Smith
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.”

Larry and Pat · Davenport, FL

Photo of Alan Brown
Coldwell Banker Realty
“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.”

Robert Dietrich · Sun City Center, FL

Photo of Paula McConahay
Century 21 Affiliated
“Andy was amazing from start to finish. His communication made the frustrating times easy throughout the process and he was a great realtor.”

Michael Griffin · Ruskin, FL

Photo of Andy Schmitt
Yellowfin 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.”

Zahima · Spring Hill, FL

Photo of Yandy Estrada
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.”

Amy L. · Land O' Lakes, FL

Photo of Leeroy Thompson
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.”

Daniella T. · Wesley Chapel, FL

Photo of Jose Mejia
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!”

Chris S. · Lakeland, FL

Photo of Darrell   Durham
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.”

Anaís Balbás · Deland, FL

Photo of Acts Home Team
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!”

Ann O. · Avon Park, FL

Photo of Kevin Jacobs
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! ”

Pat H. · Davenport, FL

Photo of Anarumo Group
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.”

Jaleel Khan · Tampa, FL

Photo of Danny Dhannu
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.”

Yamile Cuyun · Miami, FL

Photo of Mario Simauchi
Top Listing Group by eXp Realty
“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.”

Ruth M. · Zephyrhills, FL

Photo of Lottie  Creech
Future Home Realty
“She did a great job, made selling very smooth.”

Chris Bouchard · FL

Photo of The Grimes Group
Keller Williams Advantage III Realty

Winter Haven real estate Market Report.

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 $270,000 for the month of July. June’s finalized data reported the typical value of a home in the city to be $280,000—down 9.66% over the previous 12 months. For comparison, county-level data pegged home values at $314,900 in Polk County for the most recent reporting period. That number is expected to float around $312,980 in July.

Winter Haven had 126 new listings and 113 listings that went under contract in June, decreasing the area’s total available inventory to 461—down 3.96% from the previous month. Inventory is projected to have further decreased in July.

Of those 461 active listings, 34.71% reduced their price in the month of June. The median listing price for homes in Winter Haven fell 3.18% from May to June, bringing the current median listing price to $299,850. Based on projected data for July, 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 June 2025, the median time for a listed property to go pending was 70 days, compared to 103 days in June 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 July.

Winter Haven, FL real estate
41
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Winter Haven has to offer.

Winter Haven offers residents a vibrant community with beautiful lakes, outdoor recreational activities, and a welcoming atmosphere that celebrates both nature and local culture.

Winter Haven offers a lively blend of recreation, culture, and convenience, making it an appealing destination for both families and professionals. Renowned for its chain of sparkling lakes, the city is a haven for water enthusiasts, who can venture out for boating, fishing, or paddleboarding on the Chain of Lakes. Its crown jewel is LEGOLAND Florida Resort, a wonderland for families seeking excitement and imaginative play. Beyond the theme parks, the revitalized downtown district offers boutique shopping, farm-to-table dining, and vibrant community events that foster a true sense of togetherness.

Education is a point of pride, with excellent schools such as Winter Haven High and Polk State College providing quality learning opportunities for students of all ages. Art lovers can explore rotating exhibits at the Ridge Art Association or catch a performance at the Theatre Winter Haven, an award-winning community theater.

Just a short drive connects residents with the neighboring Lakeland area and major Florida attractions, while local parks like Auburndale and the relaxing Cypress Gardens add to the richness of outdoor activities year-round. Whether you're seeking scenic views, educational excellence, or a central location with quick access to Polk County, Winter Haven stands out as a community where every day brings opportunity. If you’re considering buying or selling a home in this vibrant locale, Agent Pronto can match you with an experienced real estate agent to make your next move seamless.

Woman smiling

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!

Sarah W.

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 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!


Frequently Asked Questions

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.