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

Find the perfect real estate agent in Historic Downtown Winter Haven, Winter Haven, FL

We analyze top real estate agents in Winter Haven’s Historic Downtown Winter Haven neighborhood and across the country to find you the most proven local agents, for free.

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

Compare the top real estate agents in Historic 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.

“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

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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

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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

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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

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Real Broker LLC
“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

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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

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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

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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

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Fathom Realty FL LLC
“My husband is recovering from Open Heart Surgery and very careful with the pandemic we are living through at this point in time. LuLu made him feel very at ease with everything from wearing a mask, providing sanitizer, and making sure we were not exposed to anyone when we were touring the different properties. There were questions that my husband had and LuLu was prompt to reply and gave him answers to all of his questions. She totally put him at ease. We would highly recommend LuLu Rivera to friends and family for all their real estate needs. It was a very pleasant experience, and purchasing a home can be a nightmare. But again, LuLu Rivera made sure that our dream came true. We are so happy in our new home and really appreciate LuLu’s dedication to her profession.”

William and Jill · Orlando, FL

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LIV Realty II, Inc.
“Nancy is an excellent agent and hones in on your wants vs needs in the buying process, would definitely use her again!”

Amy Mc · Leesburg, FL

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Olympus Executive Realty
“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
“Jenny Zamora was easy to work with and was very knowledgeable.”

Stacey S. · Apopka, FL

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Orlando Realty Consultants, Corp.

Learn more about what Historic Downtown Winter Haven has to offer.

Historic Downtown Winter Haven offers residents a vibrant blend of charming shops, dynamic restaurants, and lively cultural events that foster a true sense of community and local pride.

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

Historic Downtown Winter Haven offers a captivating blend of revitalized history and contemporary vibrancy, creating a truly distinct atmosphere for residents and those considering a move. Its walkable avenues are alive with locally owned boutiques and an evolving dining scene, including standout spots like Nutwood and tasteful mornings at Richard’s Fine Coffees. The Ridge Art Association sits at the heart of the cultural landscape, frequently hosting exhibitions and community events that foster a deep sense of connection. The Chain of Lakes Park invites families and outdoor enthusiasts to enjoy serene lake vistas, walking trails, and regular waterfront festivals.

Educational needs are thoughtfully served by neighborhood schools such as Winter Haven Senior High and Jewett School of the Arts, recognized for their engaging curriculums and co-curricular excellence. For live performances and entertainment, the Historic Ritz Theatre continues to be a community anchor, delivering an eclectic calendar of concerts, plays, and local gatherings.

Conveniently positioned near Lakeland and offering easy exploration via the Central Avenue Historic District, Historic Downtown Winter Haven captures the spirit of innovation while cherishing its storied past. The community’s unique energy, thriving local business scene, and commitment to preserving its heritage make it a standout destination for families, retirees, and professionals. Whether buying or selling, Agent Pronto can help you navigate the possibilities in this delightful district, ensuring a smooth and personalized real estate experience.

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 Historic 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.