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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 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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“Kristie Moore, is the best agent to work with. She is very knowledgeable and has a ton of resources to make the process smooth. I have used Kristie Moore in 5 different transcations and it ended with both parties very happy. Agent of the year!!!!”
“Kathy Bradley took the time to take my family and I to many, many properties and was so helpful in the process. We worked together for months and she helped my family get in the house that was perfect for all of our needs. She made her self available to answer any questions or concerns we had. I would highly recommend her.”
“The Stellern team was instrumental in the successful purchase of our forever home. We could not be more pleased with the results and are so thankful for their guidance.”
“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 November 2025. *
Winchester had 1 active listings in September, including 5 new listings. Overall, active listings were down 0.0% from the previous month.
The median listing price for homes in Winchester fell 5.04% from August to September, bringing the current median listing price to $245,000. Based on projected data for October, listing prices may continue to fall.
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.
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 covering the housing market in and around Winchester. 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. Find your Winchester Realtor® or real estate agent today.
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