“Valeria Amarante when above and beyond and exceeded my expectations. Would recommend to anyone. She is very attentive, patient, and understanding.”
Century 21 Scala group
- Agent Pronto
- Connecticut
- Winchester
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Compare top Winchester real estate agents.
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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“Working with Leslie was incredible. As a first-time home buyer, I was nervous about the process and didn't really know where to start. Leslie made finding and purchasing my home an enjoyable and easy experience. She was prompt, passionate, and beyond helpful. Thank you Leslie!”
eXp Realty
“Absolutely amazing experience! Nicole truly listened to my needs, took care of every detail, and got things done quickly and efficiently. She was my voice when I was busy with work and family ensuring nothing was dropped. Beyond being a fantastic agent, she's just a genuinely great person. Highly recommend!””
Century 21 Clemens Group
“Wonderful trustworthy agent. We couldn't ask for a better experience selling our property. Highly recommend Chad!”
Century 21 All Points
“Matt was great. He hung in there for a very long court process and ultimately made the sale go through. Matt was a real pleasure to work with.”
Century 21 Scala Group
“I’ve known Adam since our college days, and he’s been a trusted friend ever since. Back in 2016, he helped my wife and me buy our very first home in Connecticut, and now, nearly a decade later...he guided us through another milestone with the purchase of our commercial property in Avon. What stands out about Adam is not just his professionalism, guidance, and deep knowledge of the real estate market, but also his ability to coach and support us like a true partner. Beyond being an excellent realtor, he’s someone we know we can always trust and that’s invaluable. We’re very grateful for his expertise and friendship over the years.”
Century 21 Clemens Group
“Jennifer is an amazing person! She is Wonder Woman! She is extremely dedicated to her job and focused on her clients happiness. She found us an amazing house in such a short period of time. We are beyond happy”
East Coast Realty LLC
“Virginia worked well with me to sell my home. Communication was easy and she was always on time”
Century 21 Alliance Realty Group
“Allison was amazing! She was knowledgeable and very patient not only when purchasing my home ,but also in the sale of my property. I appreciate her and I highly recommend her!”
Century 21 Clemens Group
“Patricia was an amazing person to work with. She was always available to speak about our concerns as new home buyers. She explained the whole process with so much detail that as new home buyers we can understand. She was very professional and down to earth. We can't thank Patricia enough for all she did to help us find our first home!”
Century 21 Scala Group
“I've known Brittany for years through professionally and called her when we were considering buying. I appreciated the professionalism, realism and smart strategy that she brings to the table and extended to me and my family. The recent purchase was for a home a family member would be living in and initially we weren't sure who or how we would finance it, nor which town. Brittany took the time to understand our needs, provided thoughtful suggestions and listened to everyone's ideas (not easy with three highly opinionated family members). In today's scarce inventory market it took several months to find what we needed and Brittany was patient, focused and responsive throughout. Call her and see for yourself.”
eXp Realty
“Sandy is very professional, paying attention to details and always ready to help”
Century 21 Scala Group
“What makes century 21 top is people like Osvaldo, hi love what hi do , and make us feel like home thank hod for his life.”
Century 21 Scala Group
“Denise was very professional and very knowledgeable about condos in my area. She was always willing to help me with any issues that came up, and I was very appreciative of that, since I have a very busy work life. Thank you Denise for all your help, outstanding job!!!”
Century 21 Allpoints Realty
“Armin has helped me purchase two different properties within less than a year. I remember countless times where Armin spotted something in a property (good & bad things) that I completely missed. Armin is truly a professional who knows what he's doing & he will help you find the property that is best suited for you. Thanks again Armin!”
Century 21 Scala Group
“Sandie & her team were great, I highly recommend them!”
Keller Williams Legacy Partners
“Lisa has many qualities that make her the perfect real estate agent. She is personable, professional, knowledgeable about her profession and handled many aspects of the sale so that I did not have to worry - I would use Lisa's services in the future most definitely.”
Century 21 AllPoints Realty
“Agent Pronto referred us to The Bella Group LLC. Jeff's professionalism, kindness, and knowledge of Connecticut made the experience marvelous. We are from New York City, and he literally showed us properties in many counties. His knowledge of many areas made it possible for us to find the perfect house for us. Jeff made sure that we were receiving daily listings. He always kept us updated regarding the things that needed to be taken care of before the closing of the new house. Jeff went above and beyond in making sure that everything went smoothly with every aspect to be able to stay on target and do the closing of the house on time. We appreciate his help and professionalism throughout this process. We definitely recommend Jeff as a realtor.”
The Bella Group LLC
“A number of agents contacted me through Agent Pronto and all were very informative. I chose Amy Rio because she was the first to contact me and I felt very comfortable with her handling the sale. She was excellent, and I couldn't be happier with the outcome. I would recommend Amy to anyone. I'd also like to thank Agent Pronto for having her contact me.”
Executive Real Estate
“My real estate agent, Jeff Gardner, was outstanding! Jeff took the time to get to know me. Jeff was not pushy, he listened to my concerns and gave me good professional advice in putting my house on the market. My house was sold in one day. I could attribute it to Jeff. I could not find a better agent than him. I found in him a competent, very professional agent and above all, a great human being. I would highly recommend Jeff. Thank you!”
The Bella Group, LLC
Learn more about what Winchester has to offer.
Winchester offers residents a welcoming, close-knit community with quality schools, plentiful outdoor spaces, and convenient access to shops, services, and regional amenities.
Winchester pairs small-town character with exceptional scenic beauty, making it a compelling destination for anyone considering relocation within the northwest Litchfield County. Outdoor enthusiasts relish year-round recreation, as the sparkling waters of Highland Lake—home to water sports, fishing, and lakeside gatherings—anchor the town’s vibrant social life. For hiking and tranquil escapes, Winchester’s proximity to the Mad River Greenway and Winchester Land Trust preserves invites you to explore New England woodland at its finest.
Families appreciate Winchester’s educational options, including The Gilbert School, which provides a challenging curriculum with robust support for arts and athletics. The town’s compact downtown, located in the Winsted section, offers a delightful blend of independently owned shops, cozy cafes, and inviting local restaurants. The celebrated American Mural Project and the creative programming at the Northwestern Connecticut Community College add cultural vibrancy, ensuring a rich educational environment for students and lifelong learners.
Residents benefit from Winchester’s easy access to the professional opportunities and entertainment of Torrington, while still enjoying the peace and tight-knit spirit that define this historic Connecticut community. Its beautiful Victorian and Colonial homes, supportive school system, and preserved natural landscapes combine to create a setting where life feels both purposeful and relaxed.
If you are planning a move to or from Winchester, Agent Pronto can connect you with trusted local agents to help you navigate your real estate journey with confidence. Whether you’re searching for a lakeside retreat or preparing to list your property, their expert assistance will make the process seamless.
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 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.
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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. Find your Winchester Realtor® or real estate agent today.
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