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Information and statistics on the latest trends in the Bennington County real estate market, updated for May 2026. *
Inventory in Bennington County has grown, with 170 homes on the market, up about 13 percent from the prior month and 14 percent year over year. Contract activity is also picking up, as 56 homes went under contract and pending sales are running more than 21 percent higher than a year ago, supported by 61 new listings that are up nearly 20 percent.
Pricing is adjusting to this added supply, with the typical home value at about $401,000, down 6.53 percent from last year and 3.26 percent from the prior month. Compared with Vermont overall, where the typical value is roughly $437,800, Bennington County is trending a bit softer even though the county is still categorized as a Seller's Market with about 5.9 months of supply.
Listing behavior reflects this shift, as the median list price has moved up month over month to $499,000 while about 15 percent of sellers are lowering their asking prices. Homes are taking longer to sell than last year at 109 median days on market, even with a 16 percent monthly improvement, and buyers are paying roughly 95.96 percent of list price with only about 10 percent of sales closing above asking. To navigate these mixed signals, both buyers and sellers can benefit from Agent Pronto connecting them with a local real estate agent who understands the current dynamics in Bennington County.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Bennington County offers residents a high quality of life with access to outdoor recreation, vibrant arts and culture, close-knit communities, and strong local services and small businesses.
Bennington County offers small-town accessibility with practical connections to regional hubs. Centered on Bennington, the county stretches from historic mill villages to rural hillsides, with convenient routes to Albany, the Berkshires, and the Capital Region.
Daily life is grounded in walkable downtowns and year-round amenities. In Bennington, residents frequent the local shops and cafés around Four Corners and enjoy exhibits at the Bennington Museum. Outdoor access is a major draw, from hiking the Molly Stark Trail to exploring the Appalachian Trail corridor and scenic overlooks near Woodford. Winter brings skiing and riding within easy reach of Manchester and regional mountain resorts.
Families appreciate neighborhood schools and cultural options, including performances at Bennington Performing Arts Center and community programs through Southwestern Vermont Health Care and local recreation departments. Everyday errands are straightforward, with groceries, healthcare, and services clustered along Routes 7 and 9, while independent restaurants and breweries give each town its own character.
Housing choices range from classic village homes in North Bennington and Old Bennington to country properties with acreage, plus in-town condos and apartments that reduce maintenance and commute time. Understanding micro-markets like Shaftsbury back roads or in-demand streets near schools can make a real difference.
A knowledgeable local real estate agent can explain zoning, septic and well considerations, winter access, and price trends by neighborhood, reducing stress for both buyers and sellers. Agent Pronto connects you with that kind of on-the-ground expertise so your move in Bennington County feels straightforward and well supported.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Melissa Young was incredibly attentive and knowledgeable which was critical for me as a first-time home buyer. She helped me win my very first bid with a strong offer and guided me through challenges with the appraisal process. She sets the bar high and I am so happy with my beautiful first home in Chicago!”
“Justin was outstanding to work with in helping us sell our investment property. He was incredibly responsive throughout the process, sourced and coordinated the repairs needed to get the property ready, and quickly found a qualified buyer. He also navigated strict lender requirements and managed the transaction end to end, which gave us confidence as we were out of state. We highly recommend Justin to anyone looking for a knowledgable and proactive real estate agent.”
“Michelle was very responsive and provided us with all of the pertinent information concerning the purchase of our property, I would definitely recommend Michelle Olds to handle any real estate transactions.”
“The Best Realtor in Utah!! Hands down the best experience! They handled everything so fast and made sure we were comfortable and understood everything!! Definitely will be using them again and referring him to everyone I know!!!”
“We continue to be so pleased with how Trista DeLunger worked for us and with us when we had any question - she was very thorough in her research before giving us her opinion and an accurate answer concerning the home buying process!”
“Made the process quick and painless.”
“The level of service when we initially purchased our property combined with Jacqueline's friendly attitude, led us to unquestionably choose her to be our realtor when it came to selling our home. Her level of professionalism is beyond question and all her dealings with us have been wonderful. We were so happy she was able to be our realtor when we purchased our new home too. I would recommend her to anyone looking for a very experienced and competent realtor. She is a joy to work with! The fact that she and her partner, Lynne Redmond, work as a team really is helpful. I cannot recommend them both enough.”
“Jessie was amazing! From start to finish, he met all of my expectations. I'm very happy he was there for us and helped us sell our house.”
“We loved working with Sean. He listened closely to what we wanted and knew exactly where to look. Throughout the entire buying and selling process, he was consistently knowledgeable and always had answers to our questions. Our sale went incredibly smoothly, and we credit that to Sean’s professionalism. We would absolutely work with Sean again.”
“Lindsey was great and did a fantastic job”
“Excellent all”
“Lee is fantastic. Very responsive and always there to help and provide support. I highly recommend him. Best realtor Ive ever used.”
“Working with Lena on the purchase of our home was truly the best decision. From the very beginning she went above and beyond. Her knowledge, patience and kindness made the entire process much easier and less stressful. Highly recommend her for buying or selling. She is exceptional!”
“We were "interested" but had not made a decision to move and Dane Gates was still very accessible and open about the process. His availability and willing to work with uncertain Buyers made a difference in our decision to finally move. We are happy with the new home and even after closing on the new home, Dane Gates has made himself available to us. Dane Gates has even provide input and suggestions around the Market and ways to help sell our current home. I would recommend Dane any time.”
“She is pleasant to do business with and she did a good job.”
“I had a great experience working with Katelyn to sell my land. From the beginning, she set clear expectations and communicated consistently throughout the entire process, which made everything feel smooth and manageable. Her knowledge of selling properties like mine was evident right away. She provided excellent guidance on pricing and marketing strategies, which ultimately helped attract the right buyers. Anytime I had a question or when potential buyers reached out, she was quick to respond and always kept things moving forward. On top of that, she’s incredibly personable and easy to work with, which made a potentially stressful process much more enjoyable. I would absolutely recommend her to anyone looking to buy or sell property.”
“Dustin Gilbert was great to work with. He was very responsive and cooperative throughout the entire transaction. There were a few things that he assisted me with throughout the process that many other agents would have ignored. He is a very helpful and honest agent.”
“When Randy said he would take care of everything, he meant it. Even when we had furniture that we could not take with us. He took care of it. We moved our mother a couple states away from California and Randy was very good at communicating the process of getting the house ready to market. Even better, we go the price we wanted! I would highly recommend Randy as your next professional realtor. Thank you Randy!!!”
“James was an absolute pleasure to work with while buying our first home. The home buying process can be complex and stressful but James helped us feel confident and informed through each step, from the initial consult to closing day. He is knowledgeable, professional, personable, and was always prompt. We would highly recommend James!”
“We’ve used Chris Morris as our realtor for our last two home purchases, and he has been great to work with. He truly listens to the buyer’s needs and makes the process feel smooth and personalized. I always recommend him to anyone looking to buy a home!”
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 Bennington 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 Bennington County Realtor® or real estate agent today.
