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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 Chester real estate market, updated for October 2025. *
Chester had 3 new listings and 2 listings that went under contract in August, decreasing the area’s total available inventory to 7—down 0.0% from the previous month. Inventory is projected to have further decreased in September.
Of those 7 active listings, 42.86% reduced their price in the month of August. The median listing price for homes in Chester grew 68.35% from July to August, bringing the current median listing price to $425,000. Based on projected data for September, listing prices may continue to grow.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Chester offers residents a charming blend of scenic beauty, rich history, and a tight-knit community atmosphere that celebrates outdoor adventures and local culture.
Chester blends classic village beauty with everyday practicality, where the town green anchors galleries, cafés, and antique shops, and the distinctive Stone Village showcases granite block homes. Community life hums year-round, from artisan fairs to seasonal festivals, all supported by helpful services and updates from the Town of Chester.
Families value Chester’s strong academic foundation through the Two Rivers Supervisory Union, including Chester-Andover Elementary School and Green Mountain Union High School. The Whiting Library adds depth with robust programming and a welcoming space for readers, remote workers, and lifelong learners.
Outdoor time is easy to prioritize. Trails and river walks thread through town, while downhill devotees are minutes from Ludlow and its renowned Okemo Mountain Resort. For hiking, leaf-peeping, and sweeping valley views, Ascutney State Park is an accessible favorite in Windsor County. Nearby Grafton and Springfield expand your dining, arts, and service options; the latter is home to Springfield Hospital for comprehensive care.
Whether you’re drawn by historic architecture, a lively small-business scene, or four-season recreation, Chester offers an easygoing pace without sacrificing convenience. If you’re considering a move, or planning to list, Agent Pronto can connect you with a top-performing local real estate professional to help you navigate the market with confidence.
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 Chester. 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 Chester Realtor® or real estate agent today.
