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“Shane was very personable and stuck with us for over a year and showed us multiple properties. He was very quick to get us in to see for new homes for sale. Shane explained the selling process of our home step by step and kept us updated throughout the selling process. Shane is great to work with and we recommend him to all of our family and friends.”
“Penny knows the Poconos and the buyers moving to the area very well. She is very professional and was extremely helpful throughout this sales process. She is also a pleasure to work with and always keeps a great sense of humor. We highly recommend Penny to anyone buying or selling a house.”
“The entire experience was totally focused on making sure our needs were met. Gregg, his staff, and recommendations allowed us to handle the entire process from start to finish in a very positive manner. His ability to provide what we needed to close made the entire process professional. Thank you Greg and your team and providing an excellent legal resource who also were great. Would recommend Greg o anyone who would ask.”
“Mike was excellent in every aspect of this sale. Exclusively use Mike for all my property needs.”
“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.”
“Chris is a great guy to work with he is at the top of his game when it comes to a realtor he is very professional and curtious constantly on the go and fast with the documentation to get the job done”
“We consider ourselves lucjy to have found Lauren Espey. She had to deal with an extrordinary home sale with various negotiations and a fluid set of ever changing circumstances. Her depth of knowledge, previous experience and communication abilities were excellent.”
“You guys Rocked That's why you're my agent. Thanks Gracias.”
“I cannot be happier with Zack for his honesty, hard work and positive attitude to all the problems and endless questions. I cannot recommend him more to anyone looking for a property in PA.”
“I had an amazing experience working with Sherry. From start to finish, she made the home-buying process smooth, stress-free, and even enjoyable. Sherry was knowledgeable, patient, and always quick to answer my questions. Their guidance helped me find the perfect home, and I couldn’t be happier with my purchase. I highly recommend Sherry Pitman to anyone looking to buy or sell a home!”
“Todd was great to work with. Very communicative, and helped us close this as quickly as possible.”
“Amanda was great! I found her from wanting to see a house on Zillow and we bought and moved across country try. She was excellent at every single thing from beginning to close. You have set the bar so high I don't know how other realtors will be able to keep up to you. Thanks again for everything.”
“Lorie and her team were absolutely wonderful to work with. They were with us every step of the way and any issues that came were handled promptly and with the utmost professionalism. We would recommend Lorie and her team to everyone we meet for their real estate needs.”
“So Yong was excellent in her knowledge. She was very patient and understanding with me with my lack of selling property. She was professional at all times, easy to talk to you and extremely knowledgeable in the real estate market! She gets the job done! I highly recommend her to all!”
“We recently relocated from Indianapolis to the Michiana area and worked with Barketa Kearns as our realtor — she was fantastic! From day one, her deep knowledge of the area helped us understand the neighborhoods and what we could realistically afford. She was honest, thoughtful, and always respectful of our wishes, offering guidance without ever being pushy. Barketa was incredibly attentive to the details, even stepping in to do virtual tours when one of us couldn’t be there in person. And when she wasn’t available, she made sure other agents at Century 21 Circle stepped in to help — one of them even came to pick us up when our car broke down! That kind of care and flexibility made all the difference. Her professionalism, patience, and dedication turned what could’ve been a stressful move into a smooth and even enjoyable experience. We truly couldn’t have asked for a better partner in the process!”
“Ryan was very helpful from day one! His willingness to help was superb! He always responded to my texts in a timely manner even on Sundays! Ryan understood exactly what I was looking for in a house even when I wasn't sure. Most importantly he was very encouraging when I was ready to give up on ever finding the perfect house.”
“Mohammad was professional and a top tier realtor. He always had my best interest in mind , offered a great strategy and advice, and in the end, I got a great deal that I'm happy with. You can't go wrong with using Mohammad as your realtor.”
“Amanda made the home purchasing process a breeze. Working with Amanda gives the feeling of working with family. Amanda is very caring and goes far and beyond to understand the needs of one's family and their desire in a home. Amanda will advocate and communicate clearly on your behalf and she goes far and beyond to ensure that you will understand everything throughout the process, Making herself available when needed. She's simply the best!!!”
“Shawn did a fantastic job in helping get this property sold. He is always immediately responsive to every question no matter how many. His confidence is obvious thru how easily he answers questions leaving you no doubt of his previous research.”
“I have bought 7 personal residences before as well as many investment properties and Bob Limosani was by far the best real estate broker i have ever worked with. Unbelievable customer service and superb knowledge of the professiona and of the the area.”
Information and statistics on the latest trends in the Windham County real estate market, updated for September 2025. *
The typical home value in Windham County is projected to be $421,500 for the month of August. July’s finalized data reported the typical value of a home in the county to be $395,000—up 5.33% over the previous 12 months. For comparison, state-level data pegged home values at $430,800 in Vermont for the most recent reporting period. That number is expected to float around $433,000 in August.
Windham County had 118 new listings and 71 listings that went under contract in July, increasing the area’s total available inventory to 341—up 15.99% from the previous month. Inventory is projected to have further increased in August.
Of those 341 active listings, 13.78% reduced their price in the month of July. The median listing price for homes in Windham County grew 1.02% from June to July, bringing the current median listing price to $494,000. Based on projected data for August, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In July 2025, the median time for a listed property to go pending was 47 days, compared to 37 days in July 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this August.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Windham County offers its residents a vibrant blend of scenic natural beauty, rich cultural heritage, and a welcoming community atmosphere that inspires both relaxation and adventure.
Windham County blends river valley scenery with mountain energy, giving residents four distinct seasons of culture, outdoor adventure, and small‑town convenience. The county’s cultural anchor in Brattleboro fuels a lively arts calendar, highlighted by contemporary exhibitions at the Brattleboro Museum & Art Center, local theater, and a year‑round market scene. Skiers and riders gravitate to Dover for big‑mountain terrain at Mount Snow, while hikers and cyclists enjoy miles of trails along the West and Connecticut rivers and quiet backroads dotted with farmstands.
Families appreciate the county’s strong public options through the Windham Southeast Supervisory Union, known for student support and community engagement, as well as the Windham Regional Career Center’s hands‑on pathways. Higher‑ed opportunities add another layer: Landmark College in Putney is nationally recognized for its focus on students who learn differently, and the region’s music and language programs draw talent from around the world.
Healthcare access is anchored by Brattleboro Memorial Hospital, and everyday life is enriched by programs at Retreat Farm and the storied Harris Hill Ski Jump. Housing choices range from in‑town Victorians to slopeside condos and country homes with workshop space, offering flexibility for commuters, creatives, and remote professionals across Windham County.
Explore the Brattleboro Museum & Art Center, plan ski days at Mount Snow, learn more about the Windham Southeast Supervisory Union, and discover Landmark College’s unique mission. When it’s time to buy or sell, Agent Pronto can connect you with a local expert who knows the market, the schools, and the lifestyle you’re seeking.
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 Windham 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. 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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