We analyze thousands of real estate agents in Windsor County and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for September 2026. *
* 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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Information and statistics on the latest trends in the Windsor County real estate market. *
July 2026
Monthly data for the latest available year.
Monthly supply and activity totals for the latest available year.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026).
Year over year, Windsor County home values have inched up, with typical sale prices rising a bit more than 5 percent. At the same time, the median list price has jumped nearly 30 percent compared to last July, signaling sellers are testing higher price points. Even with higher asking prices, the share of homes selling above list has increased slightly from last year.
Recent monthly data for July 2026 shows a market adjusting to these shifts. Homes are taking longer to sell, with median days on market rising sharply to about two months, and inventory has expanded to more than seven months of supply, a much higher level than a year ago.
Sales activity has cooled, with homes sold down by about a third and new listings also noticeably lower than last year, even though pending sales ticked only slightly lower. Compared with the broader Vermont market, Windsor County’s typical home value is roughly in line with the state, but local supply is higher than the statewide figure, pointing to a more balanced backdrop for negotiations. Despite this, about one quarter of sales still close above list price and the average sale-to-list ratio hovers near full asking, showing that well-priced homes can still command strong interest. In this kind of mixed environment, both buyers and sellers can benefit from Agent Pronto connecting them with a Windsor County agent who understands these trends.
Windsor County offers residents a welcoming mix of small-town charm, diverse outdoor recreation, a lively local culture, and accessible services, creating balanced opportunities for work, education, and leisure.
Windsor County feels distinctly rural and historic compared with nearby, more tourist‑driven areas, yet it offers quick access to regional hubs like Hanover and Lebanon. From the classic green in Woodstock to the mill history in Windsor, the county blends small‑town life with a strong sense of place and year‑round outdoor recreation.
Residents enjoy easy access to the Quechee Gorge, extensive trail systems at Ascutney Outdoors, and four‑season activities around Killington. Local culture runs deep, from performances at Northern Stage in White River Junction to the historic village center of Norwich. Families appreciate community schools like Woodstock Union High School and town libraries such as Quechee Library, which double as gathering places.
Every town has its own rhythm. Hartland and Hartford offer more services and commute options, while Reading and Pomfret appeal to those seeking quiet roads and open land. Housing ranges from historic farmhouses and village homes to contemporary builds tucked into the hills.
With inventory, pricing, and demand varying widely from village to village, timing and preparation matter. Partnering with the right local expert through Agent Pronto helps both buyers and sellers move confidently and strategically in Windsor County’s unique market.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Vanessa waited three years for us to sell our house while we encountered many health issue's and delayes, aways encouraging us to continue. We needed that personal friendship and encouragement through the three years and now we live in the perfect home our family was wanting. I'm so pleased with our new home and and the results of our our purcase.”
“From the very beginning, Michael and Lori Barbier were patient, knowledgeable, responsive and really listened to my wants and concerns. I could not be happier with my new home and am thankful for all the time and effort these two amazing people spent on finding me the perfect house. The right Realtor(s) make all the difference-and I definitely found the right team for me. I would highly recommend Michael and Lori Barbier whether you are buying or selling a home.”
“I cannot say enough wonderful things about Deb. She seamlessly handled both the sale of my home and the purchase of my new one. Her dedication is unmatched—she answered every late-night text and early-morning call without hesitation. She truly goes above and beyond for her clients and feels like family by the end of the process. Thank you, Deb!”
“We have worked with Amber to sell several houses and she has always done a great job of marketing and providing valuable input on house staging. She was always available for questions or willing to stop over and give input. We look forward to working with Amber in the future.”
“Melissa is a very hard worker. She did a great job in advertising my home on many media platforms and produced a wonderful video for the public to view our home. Her communication is top notch and keeps the client updated on changes regarding home. Kind and understanding . I highly recommend her to my friends and family.”
“Heather is truly talented. She took the time to understand our needs, never made us feel pressured, and helped us come up with a game plan for a more complex selling and rent back scenario. Heather is responsive, kind, knowledgable, flexible, and professional. She did a phenomenal job marketing our property and worked very well with the buyers. We would highly recommend Heather to all our friends and family.”
“I worked with Nick to buy my first house when I moved back to the area. He's been helping me find my next house for a few years and has stuck with me, always going to show houses I thought might be a fit, but never panned out. We found this place and he was great about everything, particularly at the end when he had to do stuff as my agent and for the seller's agent - getting items signed and pushing them for closing dates. While I hope to not buy another house anytime soon, I would definetely recommend Nick to anyone looking to buy or sell!”
“As a first time buyer Jessica helped me immensely with her patient approach and answering zillions of questions that usually comes up as a first time buyer. Her knowledge on local property scene is top notch.”
“Helped me with coop purchase. Very knowledgable, and professional . Highly recommend.”
“Knowledgeable, helpful and very accessible”
“Buying my home was an absolute breeze with Sheri Chablis on my side. She is the most down-to-earth person I’ve ever worked with, making the whole home-buying process completely stress- and anxiety-free. Sheri’s diligence and work ethic are out of this world. She genuinely cares about her clients and works with so much heart. I can’t praise her enough—a thousand kudos to Sheri!”
“We truly cannot say enough amazing things about Sharon! She is honestly incredible and, in our opinion, the best realtor around. From the very beginning, it was so clear that she genuinely cared about us and wanted to make sure we found the right home for our family, not just any home. She listened to everything we were looking for, took all of our wants and needs into consideration, and was incredibly accommodating throughout the entire process. She was always easy to communicate with, supportive, patient, and made what could have been a stressful experience feel so much easier. We always felt like Sharon had our best interests at heart, and we are so grateful to have had her by our side while finding our new home. We would recommend her in a heartbeat to anyone looking for a realtor. She truly goes above and beyond for her clients!”
“Kristi was straight forward about the whole process. Completely upfront and honest as well as extremely knowledgable on all aspects of selling. If she did have the answer she researched the answer for us. Wish i could have wrapped her and her family up and brought her with us to Texas. I would 1000% recommend her services. With out a doubt expert in her work. Thank you again!!!!”
“Was impressed from the beginning when the owner answered the phone and made an appointment within a day or two to come out to the property. When we decided to put the house on the market, they were extremely professional And answered all our questions. The photographer came out promptly, and took amazing pictures of the property. It was listed the next day,and our house sold in less than a week. Andrew McCatty was our broker. He could not have been more knowledgeable or professional. Any questions that we had, Andrew either answered the phone or got back to us very quickly. Highly recommend Andrew and Century 21 Circle. Would only work with them again and would recommend them to family and friends.”
“Katerina Alix epitomizes what the ideal real estate partner is: trustworthy, communicative, personal and supportive. Her local knowledge was paramount to the success of us finding our home in the city and neighborhood we wanted. Her attention to detail is unmatched; she knew to look for details and ask questions that never crossed our minds. She was honest in her opinion, but always supportive in helping find the home that matched our preferences. Katerina responded in a timely manner to all of our texts and emails. She went above and beyond expectations. When we requested something out of the ordinary, she did it- including going back to the property during the closing process, measuring rooms, and sending us videos. If you have an opportunity to partner with Katerina, I would highly recommend her. She'll be your advocate. Katerina is remarkable and we are grateful for her.”
“La mejor de todos los tiempos”
“As a first-time homebuyer, I had a lot of questions and concerns. My agent, Lee Hurst, was incredibly patient and understanding. He took the time to explain every detail and was available whenever I needed him. Lee's experience and deep understanding of the market were invaluable. He was professional, helpful, and quick to respond. His keen eye for detail and understanding of my needs were commendable. I am very happy with my purchase!”
“Monica is phenomenal! I truly don't know what I would have done without her expertise, guidance, and understanding. She's a blessing and beautiful person inside and out. Will definitely recommend her to everyone I know.”
“I highly recommend Bob Gliwa for all of your real estate needs! I’ve had the pleasure of working with Bob on multiple occasions over the years, both buying and selling properties, and he has consistently gone above and beyond every time. Bob is knowledgeable, professional, responsive, and truly cares about his clients. Whether I was buying or selling, I always felt that he had my best interests in mind. His experience, attention to detail, negotiation skills, and ability to make what can be a stressful process feel much easier really set him apart. After working with Bob on numerous properties, I wouldn’t trust anyone else to handle my real estate transactions. If you’re looking for a realtor who is honest, experienced, dependable, and genuinely committed to getting the best results for his clients, I highly recommend Bob Gliwa. You won’t be disappointed!”
“I drove Deborah crazy doing this sale and she hung in there like a trooper she sold my house within 5 days she done an excellent job, thank you for everything!!!”
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 County. 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 County Realtor® or real estate agent today.
