We analyze top real estate agents in Winchester 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.
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.
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“When I contacted several realtors to start the process of selling my home, Patty and Alexa were the only ones willing to come by and provide advice as I completed renovations on my property. They were able to give me some tips on how to make my home more saleable. I was very comfortable with them, and even though I was an experienced seller, they helped me to negotiate through the inspection process. Recommend them highly.”
“Kathy is absolutely amazing! She's very professional, knowledgeable, and has been very helpful every time we use her as our realtor! I can't recommend her enough!!”
“Kathy Willenbrink is fantastic & was very patient with me, as I am a first time homebuyer. She's extremely knowledgeable and goes above and beyond. Other family members also will be working with Kathy in the near future involving a sale of a home. Obviously, we are very pleased with her services.”
“Megan was amazing. I was going through a stressful situation and Megan made it easy for me. She is knowledgeable and hard working. I highly recommend her to everyone”
“I can not say enough about Pam! She is a real fighter. Never say die. If I needed one person in my corner, I want it to be Pam! She is my HERO!”
“Upon giving my information, I received a prompt inquiry from The Kittner Group about possibly listing my home. From there it was a very smooth process all the way through closing day.”
“Great in every way! Was very patient walking me through every step of the process.”
“I used the Gellman Team for both buying and selling. They were tremendous. Explained the entire process in detail. Would absolutely use them again.”
“My husband and I couldn't have asked for a better first time homebuying experience. Stephanie answered all of our questions, was extremely knowledgeable about the process and provided outstanding service. She also helped us narrow down exactly what we were looking for in our first home. In the the end, we fell in love with a house she suggested we go see. We will be recommending Stephanie and her team to our family and friends!”
“Tammy knows the area and the pricing was competitive for a couple houses being sold at the same time. Selling our home before it hit the market was a win-win situation for us all. Tammy made it happen and in a professional manner.”
Information and statistics on the latest trends in the Winchester real estate market, updated for August 2025. *
Winchester had 1 active listings in July, including 4 new listings. Overall, active listings were down 0.0% from the previous month.
The median listing price for homes in Winchester grew 5.51% from June to July, bringing the current median listing price to $287,450. Based on projected data for August, listing prices may continue to grow.
Winchester offers a welcoming, close-knit community with parks, local shops, accessible schools, and opportunities for neighbors to connect in a safe, comfortable setting.
Winchester rewards residents with a calm, residential pace and everyday convenience. Tucked within St. Louis County and just off the Manchester Road corridor, it sits minutes from the shopping, dining, and recreation options in nearby Ballwin, Manchester, and Ellisville. Tree-lined streets, well-kept yards, and walkable blocks give the area an easygoing feel, while quick access to major routes keeps regional commutes straightforward.
Families appreciate that the neighborhood is served by the highly regarded Rockwood School District, known for strong academics, arts, and athletics. Learn more about programs and calendars through the official Rockwood School District website. Weekend plans are easy, too: the Daniel Boone Branch of the St. Louis County Library offers story times, maker programming, and study spaces, making it a reliable hub for learners of all ages.
Outdoor time is a highlight here. Trail runners, cyclists, and paddlers can be at Castlewood State Park in minutes for bluff-top views, river access, and shaded singletrack. Closer to home, residents enjoy pocket parks, youth sports, and seasonal events throughout the year, with everyday essentials—from coffee to groceries—right along Manchester Road.
If you’re weighing a move, Winchester combines small-city peace with big-county convenience, a smart pick for first-time buyers, downsizers, and anyone seeking a simple, well-connected home base. When you’re ready, Agent Pronto can introduce you to a top local agent—whether you’re buying, selling, or both.
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.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Winchester 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.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Winchester. 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!
Tips and market insights to make your Winchester 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.
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.
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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