We analyze top real estate agents in Windsor 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 September 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.
We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent.
“We've been working with Lisa for many years, she is always looking out for what's best for us. We've also referred her multiple times to family and friends. We're forever grateful to have such an amazing person in our lives!”
“Adam was most professional and knowledgeable. He was understanding with our needs as well as being spot on with everything that was presented to us from making our offer on our new purchase to listing as well as pricing our home .”
“We are beyond grateful for Shawnai! She helped us find the perfect home, and we absolutely love it. The process was long and had its share of ups and downs, but she made it bearable every step of the way with her professionalism, helpful tips, and encouraging chats. She was always responsive, knowledgeable, and patient, taking time to explain every step so we always felt confident and informed. She handled everything flawlessly, worked seamlessly with all the other professionals involved, and made sure no detail was overlooked. Most of all, it was clear how much she truly cared about us finding not just a house, but the right home for our family. She put her whole heart into the process, and we always felt supported and prioritized. We can’t thank her enough for making this milestone possible. I highly recommend her to anyone looking for a realtor who goes above and beyond!”
“Amy is extremely knowledgeable and skilled. She helped us achieve more than we expected. She gave excellent advice on how to best prepare the house and offered recommendations for very reliable, competent contractors and vendors. She priced the house well and handled negotiations skillfully. The process, from start to finish, was extremely smooth and well-managed.”
“If not the most talented and detail-oriented realtor, Michelle Silverio, is among them. Thank you for your help acquiring our properties. We greatly appreciate all the long trips to help us achieve our goals. Thank you Michelle and we hope that your professionalism and charisma brightens many other families lives.”
“Sheri was incredibly knowledgeable, patient, and helpful throughout the process of buying our first home. Had great attention to detail and pointed out things we hadn’t even considered. We would highly recommend Sheri!”
“We've know and interacted with dozens of local Brokers over the past 30 years by providing catering services and being involved with Broker open Houses. We've seen & experienced both excellence and mediocrity in some of our interactions. Brad proved to be in a league of his own in our experience. He was diligent, attentive and communicative beyond expectations and proved to be a most excellent choice for our Sale. In every interaction he treated us as partners in the sale, he listened attentively but most of all, he was a trusted advisor and a terrific communicator. We'd recommend him to anyone who wishes to work with him as diligently as he works and attain the best financial return on your investment, guided by Brad.”
“James Laney was extremely knowledgeable throughout the sales process. He did an outstanding job in developing a strong marketing strategy which quickly resulted in the sale of my home. He planned, organized and single handedly managed a very successful Open House Event which resulted in the successful offer to purchase the house one day later. James was expremely organized and responded very quickly to any questions that I posed to him. Would highly recommend James to any potential seller or buyer.”
“Len went above and beyond during the whole process of selling my mother's home. He was kind, considerate, compassionate and extremely helpful, during an especially stressful time. I would definitely recommend him without hesitation.”
“Topnotch service! Grateful that I found him and highly recommend him for any real estate transaction you need help with. Would use him again in a heartbeat. He and his team made selling our family home so much easier than we ever expected. Thank you, Craig Celli!”
“Beatriz, Is an amazing person, no matter what you need she has your back. Weather it be a dumpster or mover's etc Beatriz works very hard for you as her team does. She did so much advertising on our house we had it sold before we could even do an open house. We also used Beatriz to buy our next house that's how much we enjoyed working with her and her team. It's hard to sell and buy in 2 months but Beatriz and her team knew it and were there for us. Beatriz and her team are amazing I highly recommend them”
“Marcia is a very knowledgeable and experienced realtor. She is always professional, prepared, friendly, and communicative. It was a pleasure working with her and I never felt anxious regarding the listing and sale of my co-op. Since I lived in that co-op for so many years, it was a scary decision to sell my unit. Marcia made it so easy. I would recommend Marcia to anyone looking for a realtor.”
“My husband and I have worked with four Realtors in 3 different markets - CA, KY & RI. Our experience with Christine - first when selling a house in 2022 and the purchase of our current home (2025) - has been unrivaled. She is professional, knowledgeable, amiable, and fully answered our many questions.”
“Very happy with the process and service received, will use Derrick again”
“Nina Sable was enjoyable to work with and her professional expertise was was appreciated.She was always available for my many questions, and showed personal interest in my needs.”
“I'd strongly recommend Jill! We felt like we were in good hands every step of the way”
“I cannot say enough positive about my experience working with Kurt. Kurt is honest, smart, personable, patient, knowledgeable, hard working, a great communicator, and professional. He has a way of explaining everything extremely well, and was always able to keep me calm when things appeared to be chaotic. I would recommend Kurt and his team in a heartbeat.”
“Kathy is absolutely everything that a seller or home buyer wants in a real estate agent. In the original purchase of our home and now with its sale, Kathy is an agent's agent. Having assigned the highest level of commendation in every category of this evaluation above, it should be clear that we consider her efforts on our behalf to be flawless. She was our agent in the beginning and she is a friend at its conclusion. Our friendship will continue for years to come. It would be my priviledge and pleasure to share my assessment of Kathy as our agent for purchase and sale with any prospective clients if deemed helpful and appropriate. I can't evaluate her with any greater clarity than to say that she is "an agent's agent" and "the best of the best."”
“tom answered every text,email and phone call promptly,he was extremely helpful and patient with us”
“Working with Farrah was a great experience. She really took care of our needs from start to finish!”
Windsor offers residents a close-knit community, convenient access to outdoor recreation, and a calm, family-friendly pace that supports a high quality of life.
Windsor offers a captivating small-town atmosphere paired with expansive landscapes, making it a standout retreat for those looking to balance tranquility with access to outdoor adventure. Surrounded by the natural beauty of the Berkshire County, Windsor’s rolling hills and lush forests are a playground for all seasons. Adventure seekers and nature enthusiasts can immerse themselves in sprawling green spaces at Windsor State Forest or discover miles of pristine hiking and snowmobile trails within Notchview, a Trustees of Reservations property renowned for its cross-country skiing in winter and beautiful wildflowers in summer.
Families in Windsor benefit from inclusion in the Central Berkshire Regional School District, which offers a range of educational experiences and enrichment programs. Local students attend state-of-the-art facilities where outdoor learning and a strong sense of community are woven into daily life.
Just a short drive brings residents to the arts and dining scene of Pittsfield, while the cultural offerings of Lenox, home to Tanglewood and other treasured destinations, are easily accessible for weekends. The sense of peace that defines Windsor is enhanced by a vibrant civic spirit, evident at events hosted at the local Windsor Town Hall and celebrated gatherings at the Windsor Pond.
Whether you're seeking the slow pace of rural living or preparing to move closer to the heart of the Berkshires, Windsor delivers a rare blend of serenity and community connection. Those considering making Windsor their next home—or listing their property—can rely on Agent Pronto to connect them with trusted local real estate experts committed to making every transition smooth and successful.
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 Windsor. 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 Windsor Realtor® or real estate agent today.
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