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.
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“Within moments of meeting Marie, we knew she would be the one to sell our home. She was extremely easy to work with, and very knowledgeable, professional, and friendly. She kept us updated throughout the entire process, and we highly recommend her for buying or selling a home.”
“James Martin understood what we wanted and needed. He worked with our schedules so we could look at houses and helped us pick the perfect house for us.”
“I wouldn't trust any other realtor except for marsha bartllet she is the only realtor that I know that truly goes above and beyond to take her job seriously anyone who is on vacation and is taking the time to make sure everything is going right is truly a professional in my book thank you marsha.”
“Joseph was right there for us when we contacted for an agent. He was open and honest with us on everything Joseph didn't stop looking for places even when we couldn't go until after 430. We both felt comfortable talking to him over all our expenses and what we needed Joseph forums us the perfect house and we would definitely use him again if needed and would recommend him to other people. Thanks from both Lee and I for helping us find our perfect new home. Connie and Lee”
“Jason was awesome to work with! Very professional and knowledgeable about the area. He was always willing to answer any questions we had, especially since we were first time sellers. Would recommend to anyone!”
“Joe is a highly experienced realtor and has excellent people skills. He listens and responds appropriately. He is respectful and friendly. Most importantly he is an expert and most knowledgable in his profession. He navigated through both the sale and purchase processes, answering and addressing all of our questions and concerns. And, in my opinion, his best feature of all is.... he is a really nice person! I am glad to know him, and we were fortunate to have him guide us through our journey.”
“Known Julie Ray Ritchie from previous experience with her. Upfront-straight forward honest person, non condescending approach, very personable yet, professional in many ways. My husband and I had previous unpleasant experienced with real estate agent/s but Julie is the best one to work with. And yes, we highly recommend her to our family friends. Cheers! to you Julie and Caldwell Banker, Nky team. Thank you.”
“Chris went above and beyond to help me, my mother, and the sale of the home . He was in constant communication and we had a great experience with him ”
“Natasha Bintz is an amazing person and a great realtor. We would highly recommend her to anyone wishing to sell their house in Kentucky. She went above and beyond to help us when we needed to sell quickly and was sweet about it the whole time. Thank you, Natasha!”
“Mary was great and pleasant to work with and I would recommend her to anyone!”
“Erin is very good at what she does. She knows the market values, the area, she is very personable and easy to work with. Her achievements were important in our decision to use Eric. I would and have recommended her to other people that have mentioned about they were thinking of buying or selling. We know several realater but we didn't want to use someone we knew, I'm glad we made that decision or we would not have meet Eric, we are very satisfied with the sale of our parents house. Eric is a great sales person and a great person, and great to work with!! You have a great Sales Lady !!!!”
“I found a wonderful realtor by the name of Tamara Cecil, she worked fast and hard to help us get our house sold. Not only did I have over 20 showings in less than two days, I also had multiple offers as well with the unicorn offer of everything we wanted. She was such a great agent and I could not have chosen anyone better to sell my home. Not only was she a great agent, but also became a friend in the process. I am telling everyone I know about Tamara!”
“I am truly grateful for the amazing experience that we had. Robin's service was above and beyond. There were many challenges in the circumstances that surrounded the sale of this house and above everything else she was so kind and considerate.”
“Jenn took a hectic situation, selling 2 properties and looking for a new property and made it stress free. She had constant open communication and went above and beyond to get our homes sold in a timely manner and get us into our dream home. I will never recommend another realtor she will be our agent and our recommended agent for life!”
“Traci and another agent from her group, Lana, helped me see as many houses as I wanted. They were very helpful and considerate. Between the two ladies, I saw so many houses and never felt pushed to buy any of them. I was informed of potential issues with houses and they respected if I didn't like something about a house. Days before I was set to go back home, Traci found a house that had just come on the market and I bought it! It has almost everything on my wish list. I couldn't be happier!”
“Lana Stephens and Traci Mitchell are a pleasure to work with. They are professional and friendly, and know their business. They not only sold my late father's townhome, they helped me completely gut and remodel it. And I live out of state! Their team put together a great plan. They kept in constant contact with plans, purchases and those things that pop-up when remodeling. I appreciate their patience, kindness and special treatment since it was my father's place. I can't think of a better fit for what I needed. I highly recommend them to work with any situation.”
“Agent Pronto helped us find a competent, efficient, talented broker at the Oatley Team!”
“We had planned on doing a FSBO. We are so thankful we did not! There were several hiccups from the other side and Lindsay handled them perfectly. I would absolutely recommend Lindsay.”
“Great job! Steve was a pleasure to work with.”
“Returning to Jason for help selling our home and purchase of our new home was a great decision. We used Jason on our first home 11 years ago and so glad we utilized him again. His market knowledge was crucial in pricing our sale and negotiating our purchase. He never rushed us, was always available for questions and worked with us for showings. A true Real Estate Professional.”
Information and statistics on the latest trends in the Winchester real estate market, updated for August 2025. *
The typical home value in Winchester is projected to be $242,100 for the month of August. July’s finalized data reported the typical value of a home in the city to be $244,700—up 6.39% over the previous 12 months. For comparison, county-level data pegged home values at $247,000 in Clark County for the most recent reporting period. That number is expected to float around $231,250 in August.
Winchester had 38 new listings and 29 listings that went under contract in July, increasing the area’s total available inventory to 73—up 23.73% from the previous month. Inventory is projected to have further increased in August.
Of those 73 active listings, 19.18% reduced their price in the month of July. The median listing price for homes in Winchester grew 5.27% from June to July, bringing the current median listing price to $279,500. Based on projected data for August, 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 July 2025, the median time for a listed property to go pending was 54 days, compared to 77 days in July 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 August.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Winchester offers residents a welcoming, tight-knit community with beautiful parks, vibrant local events, diverse dining and shopping options, strong schools, and easy access to outdoor recreation and regional amenities.
Winchester blends a friendly pace with easy access to big-city amenities, set along I-64 about 20 minutes from Lexington and at the heart of Clark County. Historic neighborhoods and a revitalized Main Street frame an active calendar of parades, concerts, and community events overseen by the City of Winchester.
Outdoor time comes naturally here. Families flock to Legacy Grove, a 30-acre park with an award-winning inclusive playground, walking paths, and a tranquil pond. Arts lovers catch live performances at the restored Leeds Center for the Arts, while the Bluegrass Heritage Museum shares local stories inside a former medical clinic. Food traditions run deep—from the hometown roots of Ale-8-One to the famous Beer Cheese Festival—paired with cafes and local restaurants that keep downtown lively. Healthcare needs are covered by Clark Regional Medical Center, and youth sports thrive at fields and gyms across town.
Schools are a point of pride. Clark County Public Schools supports strong academics, career pathways, and spirited athletics at George Rogers Clark High School, with additional opportunities through regional colleges and technical programs. Weekend adventures are close by: horse country in Paris, campus culture in Richmond, and equestrian, culinary, and arts destinations in Lexington.
From historic homes to new subdivisions, options fit first-time buyers and move-up households alike. Whether you’re relocating or preparing to sell, Agent Pronto can quickly connect you with a top local real estate professional to make your next move in Winchester seamless.
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.
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