- Agent Pronto
- Kentucky
- Winchester
Find the perfect real estate agent in Winchester, KY
We analyze top real estate agents in Winchester and across the country to find you the most proven local agents, for free.
Compare the top 25 real estate agents in Winchester
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for June 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.
“Mike was awesome. Thanks. The process was very easy and went smoothly.”
“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.”
“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!”
“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.”
“Everett Baker did an outstanding job for us. I would recommend him to a friend.”
“Turner Realty was great.”
“Agent Pronto will not disappoint! I was connected with a realtor that was familiar with my area. Terry was very efficient and made the entire process of selling our home effortless.”
“By using Agent Pronto, I was able to connect to a realtor that was knowledgeable of the area. I was also able to connect to a finance company. It made the process of buying a home so much better.”
“Agent Pronto helped us find a competent, efficient, talented broker at the Oatley Team!”
Winchester real estate Market Report.
Information and statistics on the latest trends in the Winchester real estate market, updated for June 2025. *
The typical home value in Winchester is projected to be $220,750 for the month of May. April’s finalized data reported the typical value of a home in the city to be $220,000—down 11.29% over the previous 12 months. For comparison, county-level data pegged home values at $244,950 in Clark County for the most recent reporting period. That number is expected to float around $246,930 in May.
Winchester had 32 new listings and 30 listings that went under contract in April, decreasing the area’s total available inventory to 59—down 7.81% from the previous month. Inventory is projected to have further decreased in May.
Of those 59 active listings, 27.12% reduced their price in the month of April. The median listing price for homes in Winchester fell 7.41% from March to April, bringing the current median listing price to $227,250. Based on projected data for May, listing prices may continue to fall.
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 54 days, compared to 67 days in April 2024. However, in recent months the median number of days from listed to pending appears to be rising. 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 Winchester has to offer.
Winchester offers residents a vibrant community with rich history, inviting local parks, and diverse dining and shopping options that enhance quality of life.
Winchester is a community where history, culture, and hospitality converge, creating an inviting home for families and newcomers alike. Situated just east of Lexington in Clark County, Winchester draws residents with its small-city warmth and access to big-city amenities. Locals and visitors enjoy everything from the downtown historic district with its boutique storefronts and lively eateries, to the famed Ale-8-One Bottling Company, where you can tour and taste a Kentucky original.
Education is a cornerstone here, with Clark County Public Schools providing comprehensive learning for all ages, and options like Strode Station Elementary School and George Rogers Clark High School known for strong academic and extracurricular programs. Adventure seekers and outdoor enthusiasts are drawn to the nearby wonders of the Red River Gorge, while the Bluegrass Heritage Museum offers an immersive look at local history and culture close to home.
Community spirit thrives at events like the annual Beer Cheese Festival, a celebration for which Winchester is famous, and families love visiting parks such as College Park for recreational fun. Whether you're contemplating a move or looking to sell, Agent Pronto can connect you with a trusted local agent to guide you through your Winchester real estate journey.
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 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.
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 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!
Resources for buyers and sellers.
Tips and market insights to make your Winchester 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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