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Information and statistics on the latest trends in the Chester real estate market. *
Mar 1, 2026 - May 31, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Year-over-year, Chester’s rolling three-month data shows a sharp reset in prices and a pickup in activity. The typical home value is down more than 45% compared with a year ago, yet homes sold have climbed by over 50% and pending sales have more than doubled.
Looking at the latest three-month window ending in May 2026, conditions still lean toward sellers but with more balance than before. Inventory has inched up to 13 active listings and 2.7 months of supply, while the median days on market has shortened to 37 days, indicating buyers are acting more quickly when they see the right home.
Pricing dynamics highlight strong demand despite the lower headline values. About half of recent sales closed above list price, and the average sale-to-list ratio sits above 114%, showing that well-positioned homes can still draw aggressive offers from buyers. Agent Pronto can connect both buyers and sellers with an experienced local agent to help them navigate these shifting trends and negotiate effectively.
Chester offers residents a close-knit community, abundant outdoor spaces, and a welcoming small-town atmosphere enriched by local events and scenic natural beauty.
Chester offers small-town living with practical access to work, schools, and outdoor recreation. Set along the Middle Branch of the Westfield River, it sits within commuting distance of Springfield and Pittsfield, making it a viable choice for those who want quiet surroundings without feeling isolated.
Daily life is shaped by the landscape. Residents enjoy hiking and fishing around Chester-Blandford State Forest, while the dramatic Keystone Arch Bridges Trail offers a unique walking route across historic stone rail bridges. Families appreciate the local public library, the Chester Village Public Library, as a hub for programs and community events. Dining is low key but satisfying, with local spots and more options a short drive away in Westfield.
Chester’s housing stock ranges from older village homes to more rural properties, appealing to buyers seeking space, privacy, and relative affordability compared with larger nearby markets like Northampton. Road connections via Route 20 and nearby interstates help residents reach jobs and services throughout Hampden County and Berkshire County. Public services and town information are centralized through the Town of Chester website, which is helpful for both newcomers and long-time residents.
Whether you are relocating to Chester or planning to sell and move on, a local real estate agent who understands back roads, seasonal conditions, and pricing trends can significantly reduce stress. Agent Pronto connects both buyers and sellers with the right local expertise so each move feels more manageable.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Kurt Thompson was fantastic to work with. Throughout the entire process, we knew we had someone looking out for our best interests. His years of experience were exactly what we needed to navigate a journey that can be exciting, stressful, and exhausting all at once. Highly recommend!”
“Lisa was incredible. She was always available whenever we had any questions and was always quick to reply. You could tell her main goal was to help find the perfect house. And she did just that. I would highly recommend Lisa to anyone.”
“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!”
“Sheri Barrette was a really important resource in my home purchase. She was able to get me in the property quickly, had great insight into the property value, and was able to get me an excellent final price. She gave me helpful context about the condo market and the availability of units like the one I purchased. She was also able to recommend other professionals involved in the purchase process who were just as knowledgeable and professional as she was. If I ever buy or sell a property, I would work with Sheri again. She was trustworthy and showed that she was working with my best interest.”
“Fue más de lo que esperaba muy amable excelente profesional Y sobretodo muy rápido 10 días Wao todavía No lo creo jajaja muchas gracias Michelle Silverio eres la mejor Dios continué depositando su gracia sobre ti bendiciones y Asia delante porque se que es solo el comienzo de las cosas grandes que vendrán en el nombre de Jesús bendiciones”
“El seńor Juan lopera,excelente agente vendedor respetuoso al entrar a la propiedad igual que su equipo de trabajo ,muy buena comunicación,siempre pendiente durante todo el proceso de venta. Gracias.”
“Nina Sable was enjoyable to work with and her professional expertise was was appreciated.She was always available for my many questions, and showed personal interest in my needs.”
“My experience with Agent Pronto was excellent! Robin Foley was outstanding and always kept me informed.”
“He was honest enough to direct us away from one of the homes that we looked at because of the horrible basement there. He also showed us at least 5+ homes before we settled on the one we're living in now.”
“Ms. Diane Franklin along with our representing attorney have both proved themselves to be highly reliable and proficient in performing the services necessary to assist in bringing our single-family home to market, and successfully consummating a mutually acceptable sale of the latter property. We would highly recommend Ms. Franklin for her proven level of effort, dedication, professionalism and reliability.”
“Elena is one of a kind just like how she found my perfect home for me in West Boylston, Massachusetts. I am from San Diego, California and never would have imagined to own a home in central Massachusetts but she opened my eyes to a beautiful town of West Boylston and provided great statistical feedback to help me make my decision. I am happy with my decision and a lot of it comes from a skilled and professional agent such as Elena. Highly recommend her.”
“I was recommended by a friend to call Kerry Lapiana with Prestige Homes. I am so glad I did. Kerry went up and beyond from the beginning until the end. She was always available with any questions I had and she made the offer process so easy. It didn't end there. She even took time after I closed to ask me how it was going if I needed anything additional. She went up and beyond every step of the way. I would highly recommend Kerry Lapiana and Prestige Homes to friends, family and colleagues.”
“Jocelyn Magner was amazing through out the whole purchase. She explained the process to me in detail and answered all my questions. She really cared about everything from start to finish and went above and beyond. I couldn't have asked for a better rep.”
“Sabrina and I had started discussing my home in early 2017. She kept in contact with me as the market changed and alerted me when she felt my home reached the value I was seeking. Her networking really made the difference. My home sold fast and the process was smooth and relatively easy. Sabrina’s knowledge and assistance was a huge help. Sabrina provided excellent advice and saved me time and money; there were some projects I intended to tackle before going on the market but she counseled me to wait. The times were not brought up by the buyers. Sabrina was a great asset in helping me with the sale of my home. I lived there for nearly 18 years; she kept me grounded and focused. I appreciate it!”
“From the minute we asked Jodi Donovan to be our buyer’s agent, all the way through closing on the best possible house in our price range, we were grateful to work with Jodi. Her knowledgeability, her responsiveness, her professionalism, and her willingness to go above and beyond gave us peace of mind during one of life’s most stressful events. At every stage of the process, Jodi demonstrated her fierce commitment to advocating for our family and protecting our interests. She is where passion and ability meet. I trust her completely and will hire her for all my future real estate needs. I will continue to highly recommend Jodi Donovan to everyone who tells me they’re moving.”
“I chose Angela because my brother and sister in law have worked with her in the past and stated she was great to work with! Once I called her she was in contact with me when I had questions and was quick to respond. Angela was the best through the whole process. She was prompt with communication and always talked me through anything I was wanted more info about. She was always so friendly and went through a lot of houses until I found the house for me! She was always smiling and encouraging during the whole process! Angela is the best!! Angela was always there! She gave me information that I needed and was there when she said she would be there. She always gave me information ahead of time so I would know what was expected. She was awesome!! My experience overall was great thanks to Angela!”
“Roseanne was knowledgeable through the entire process of buying our home. She knew what we wanted and went above and beyond to help us get into our new home. We highly recommend her to everyone.”
“Great Real Estate person you can't do without if you are buying or selling .”
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.
