1. Agent Pronto
  2. Florida
  3. Winter Haven
  4. 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.

Real estate in Winter Haven’s Downtown Winter Haven neighborhood.

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 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.

“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!”

Mala · St Cloud, FL

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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
“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
“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
“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

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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!”

Chris S. · Lakeland, FL

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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!”

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

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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
“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.”

Michael Hathway · Lawrenceville, GA

“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.”

Mikeal Holtzclaw-Gray · Orland Park, IL

Photo of Larry Lazar
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.”

Cynthia A. · Lake Wales, FL

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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”

Mark · Haines City, FL

Photo of Lakeia  May
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.”

Misty S. · Winter Haven, FL

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SellState Centric Realty
“Excellent job”

Blanca Luis · Miami, FL

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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 August 2025. *

The typical home value in Downtown Winter Haven is projected to be $192,500 for the month of August. July’s finalized data reported the typical value of a home in the neighborhood to be $200,000—down 41.52% over the previous 12 months. For comparison, city-level data pegged home values at $296,660 in Winter Haven for the most recent reporting period. That number is expected to float around $304,990 in August.

Downtown Winter Haven had 10 new listings and 10 listings that went under contract in July, decreasing the area’s total available inventory to 14—down 17.65% from the previous month. Inventory is projected to have further decreased in August.

The median listing price for homes in Downtown Winter Haven fell 19.32% from June to July, bringing the current median listing price to $188,750. Based on projected data for August, 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 July 2025, the median time for a listed property to go pending was 21 days, compared to -10 days in July 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 August.

Real estate in Winter Haven’s Downtown Winter Haven neighborhood.
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Seller’s Market
Seller’s Market
Buyer’s Market
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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 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.

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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 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!


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.


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