- Agent Pronto
- Florida
- Lakeland
- Winston
Find the perfect real estate agent in Winston, Lakeland, FL
We analyze top real estate agents in Lakeland’s Winston neighborhood and across the country to find you the most proven local agents, for free.
Compare the top 25 real estate agents in Winston
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for May 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.
The easiest way to find the best real estate agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
- Tell us what you need.
- Answer a few quick questions about your real estate needs so we can begin our search.
- Match with the perfect agent.
- Our personalized matching system will connect you with a top-rated real estate agent with the local expertise and experience you need.
- Meet your agent.
- Review the details of your top agent recommendations and speak with them to learn exactly how they can make your real estate journey a success.
- Buy and sell with confidence.
- While real estate decisions are among the most important financial and personal decisions we make, you can rest easy knowing that you have a proven real estate professional on your side.
Home buyers and sellers love Agent Pronto.
Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.
“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!”
“Cheryl is a very knowledgeable and professional realtor. If I have to do this again, she will be my first choice. It was amazing that after our first showing she quickly realized the type of neighborhood I want to look at, so we wasted no time.”
“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.”
“Extremely helpful and attentive to our issues and needs. Went above and beyond to be sure we had a stress-free experience! ”
“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.”
“The agent recommended by Agent Pronto sold the house in two days.”
“Agent Pronto hooked us up with the best realtor. Jim McQuade was a pleasure to work with; he far succeeded our expectations.”
“My experience with Deepak Team was above and beyond what I expected. Great team to work with.”
“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.”
“Rachel was very supportive in helping me sell my home. She never gave up until she got me the right price. She is a very good salesperson! ”
Winston real estate Market Report.
Information and statistics on the latest trends in the Winston real estate market, updated for May 2025. *
The typical home value in Winston is projected to be $215,050 for the month of May. April’s finalized data reported the typical value of a home in the neighborhood to be $210,000—up 7.69% over the previous 12 months. For comparison, city-level data pegged home values at $313,000 in Lakeland for the most recent reporting period. That number is expected to float around $319,500 in May.
Winston had 19 new listings and 24 listings that went under contract in April, decreasing the area’s total available inventory to 21—down 8.7% from the previous month. Inventory is projected to have further decreased in May.
The median listing price for homes in Winston grew 4.55% from March to April, bringing the current median listing price to $230,000. Based on projected data for May, 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 April 2025, the median time for a listed property to go pending was 60.5 days, compared to 74 days in April 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 May.
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 Winston has to offer.
Winston offers residents a charming community filled with inviting parks, friendly neighbors, and convenient access to local amenities, making it an ideal place to enjoy a comfortable and connected lifestyle.
Winston unfolds as a welcoming and conveniently located neighborhood within Lakeland, offering a relaxed suburban feel paired with easy access to city amenities. Residents appreciate the strong sense of community and the variety of experiences Winston presents, from quiet, tree-lined streets to nearby parks that invite outdoor enjoyment. Families are drawn to the area for its educational offerings, notably Winston Academy of Engineering, which is known for its specialized magnet programs and emphasis on hands-on STEM learning. Also close by is Kathleen Senior High School, providing additional options for secondary education.
The Winston neighborhood benefits from proximity to recreation and retail. The Gandy Pool, a popular gathering spot, provides lessons, fitness classes, and open swim hours, making it a go-to place for all ages. The expansive Lake Parker Park is minutes away, featuring trails, picnic areas, and lakefront vistas that encourage residents to embrace the outdoors. For shopping needs, the Lakeland Square Mall is easily accessible, hosting a range of national retailers and local eateries.
Local life in Winston is further enhanced by its connectivity to neighboring communities and regions. Its location between Lakeland’s downtown and burgeoning Plant City positions residents just a short drive from the broader arts scene, markets, and festivals, while still maintaining a peaceful environment at home.
Whether you’re searching for your next property or ready to sell in Winston, Agent Pronto can connect you with a trusted real estate expert to guide you every step of the way, ensuring your move is smooth and well-informed.
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!
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 Winston 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 Lakeland. 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!
Resources for buyers and sellers.
Tips and market insights to make your Lakeland real estate journey a success.
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. 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.
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