We analyze top real estate agents in Windsor County 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.
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“Jeff was a delight to work with! From start to finish, he was able to answer all my questions in a way that made sense to me. I felt like he became a part of the family. He was encouraging when the process looked grim. He went above and beyond to close the deal when I found the home of my dreams. I would recommend Jeff to anyone looking to buy a home!”
“Kim, the Seller’s representative, was exceptional throughout the entire process. She managed every aspect to ensure a smooth and hassle-free transition for both parties. I highly recommend her to sell your house; you won’t be disappointed.”
“We've known Gabby for a few years and have always been struck by how genuine and friendly she is. So when we heard she became a real estate agent, we were thrilled and knew immediately we would use her when the time came to buy our home. Gabby guided us through every single step of the process of buying our new family home. Her communication was exceptional—we never felt we couldn't reach out with a question, no matter how small. Most importantly, she was consistently honest and real with us, ensuring we never felt pressured and always felt looked after. We truly couldn't have picked a better agent. If you're looking for someone who will genuinely have your best interests at heart, Gabby is your person!”
“easy to work wit, professional, knowledgable, responsive”
“Shawn Gaugler is warm and personable, taking every extra step needed to ensure client satisfaction and good outcomes. She is a dedicated and hard worker, is well thought of by others in the industry, and brings a spirit of positivity to her work.”
“Working with Ryan has been an absolute privilege. Over the years I've purchased four homes with him, and each experience has reinforced that there is simply no substitute for his expertise, integrity, and commitment. He listens carefully, anticipate needs before I even voice them, and navigates every detail with professionalism and care. His market knowledge is unmatched, his negotiation skills are outstanding, and his guidance consistently leads to the right home at the right price. I trust Ryan completely and would never consider working with anyone else. Truly irreplaceable.”
“Lynn is spectacular!! 💜 She is an outstanding communicator and kept me posted throughout the process. She is professional and reliable, yet you can tell she genuinely cares and is highly supportive!! I highly recommend her and she will be my forever go to real estate agent 💗 many blessings to her 💙”
“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!”
“We are very happy and grateful to have Cathy as our realtor. She was there every step of the way on our journey to purchasing our house. She is absolutely outstanding and goes above and beyond. She responded immediately to our questions and concerns. She was professional, knowledgeable and attentive to small details. We highly recommend her to anyone looking for an excellent realtor.”
“Dawn is very special, she takes the time to understand what we were looking for, and has a wealth of knowledge about all aspects of real estate. She knows the specialties in the county and had great recommendations for us. We found our dream home and we appreciated the whole experience from searching to closing, thanks to our wonderful agent!”
“Casey was great to work with. He walked with us every step of the way providing great advice without being pushy. Even when our house didn't sell as quickly as any of us expected Casey was tenacious about getting showings and open houses and getting valuable feedback from potential buyers. We sold our house because of Casey's tenacity and hard work.”
“Reva is the only realtor we will use. Great communication, and a pleasure to work with.”
“Dave was upfront with me about the market and my expectations. He was very helpful through the process. I would recommend him to others.”
“⭐️⭐️⭐️⭐️⭐️ Elena Schmidt was incredible to work with! Anytime I texted her, she would drop everything to take us to see a house, which made such a difference in this crazy market. She was extremely knowledgeable and guided us through making a strong offer that helped us get our home! Elena is kind, attentive, and truly recognized our needs so well. We couldn’t have asked for a better realtor! Thank you for everything, Elena!!”
“Denise was fantastic to work with! So comforting and knowledgeable during a big transition in our life. Saying goodbye to a home that has been in our family since the 60s, and making sure the beauty, love, and years of hardwork put into the house was the forefront of all of the sales disucssions and marketing. She organically saw and honored all of the beauty that came with the house and effectively relayed that to any prospects. She was fantastic & would definitely work with her and recommend her for future.”
“Lena was great, she always made sure I had what I needed. Also very helpful with questions and knowledgable about her profession. I would definitly recommend Lena for your home buying journey.”
“Pam was awesome. Made the whole process easy and stress free. She priced my home right and we received our first offer the first day. We sold in a week!”
“My husband and I could not say enough great things about Katrina. She helped us through the purchase of our new home and the sale or of our old. When it came to purchasing our new home, she was extremely responsive, professional, and provided extremely knowledgeable insight into the home buying process. She was with us every step of the way and made us feel at ease throughout a big life moment! Thank you Katrina!”
“Ryan is very easy to work with. He is not pushy, and wants you to find the right home for you. Even as a first time home buyer he made us feel completely informed and confident on our home purchase.”
“I truly appreciated Brian's professional expertise and the valuable advice he shared in helping me determine the best real estate venture for my goals. His guidance has been instrumental, and I'm grateful for the insight and support throughout this process.”
Information and statistics on the latest trends in the Windsor County real estate market, updated for September 2025. *
The typical home value in Windsor County is projected to be $312,500 for the month of September. August’s finalized data reported the typical value of a home in the county to be $350,000—down 22.22% over the previous 12 months. For comparison, state-level data pegged home values at $431,500 in Vermont for the most recent reporting period. That number is expected to float around $432,000 in September.
Windsor County had 110 new listings and 114 listings that went under contract in August, decreasing the area’s total available inventory to 440—down 1.57% from the previous month. Inventory is projected to have further decreased in September.
Of those 440 active listings, 21.82% reduced their price in the month of August. The median listing price for homes in Windsor County grew 13.45% from July to August, bringing the current median listing price to $485,000. Based on projected data for September, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract has been fairly steady year-over-year. In August 2025, the median time for a listed property to go pending was 56 days, compared to 55 days in August 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this September.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Windsor County offers residents a welcoming blend of small-town charm, abundant outdoor recreation, strong local services, and a collaborative community that supports a high quality of life.
Windsor County rewards everyday life with mountain views, lively village centers, and year‑round recreation. Stroll the green in Woodstock and explore the working landscape at Billings Farm & Museum, whose award‑winning programs pair beautifully with the nearby Marsh-Billings-Rockefeller National Historical Park. Hike riverside trails above the “Little Grand Canyon of New England” at Quechee Gorge State Park, or head to Ludlow for ski days and summer lift rides at Okemo Mountain Resort. Families love the hands‑on science and raptor releases at VINS Nature Center, while galleries and theaters in Hartford (including White River Junction) enrich the arts scene.
Schools are a strong draw, with the Windsor Central and Hartford districts offering AP coursework, technical pathways, and competitive athletics. Higher‑ed energy also ripples from Norwich and across the river to Hanover, expanding access to lectures, libraries, and research partnerships. Career changers and law students value the presence of Vermont Law and Graduate School in the county. Healthcare access is exceptional, anchored by Dartmouth Hitchcock Medical Center just over the border, and daily life is convenient with I‑89/I‑91 connections and Amtrak service from White River Junction and Windsor.
From historic farmhouses to ski‑side condos, housing options align with four‑season living and weekend getaways alike. Whether you’re buying or selling here, Agent Pronto can connect you with a trusted local agent who knows the neighborhoods, the market, and how to get you moving.
Marsh-Billings-Rockefeller National Historical Park • Quechee Gorge State Park • Okemo Mountain Resort • Billings Farm & Museum • VINS Nature Center • Vermont Law and Graduate School • Dartmouth Hitchcock Medical Center
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 Windsor County 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 Vermont. 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 Vermont 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 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.
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