We analyze top real estate agents in Chesterfield 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.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
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“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!”
“If not the most talented and detail-oriented realtor, Michelle Silverio, is among them. Thank you for your help acquiring our properties. We greatly appreciate all the long trips to help us achieve our goals. Thank you Michelle and we hope that your professionalism and charisma brightens many other families lives.”
“James Laney was extremely knowledgeable throughout the sales process. He did an outstanding job in developing a strong marketing strategy which quickly resulted in the sale of my home. He planned, organized and single handedly managed a very successful Open House Event which resulted in the successful offer to purchase the house one day later. James was expremely organized and responded very quickly to any questions that I posed to him. Would highly recommend James to any potential seller or buyer.”
“Jenn was a pleasure to work with. She knew that purchasing this particular piece of property was very important to me and she made sure that it happened for me.”
“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.”
“Tanya Harvey went above and beyond in not only her service but her compassion as she sold my house. She communicated constantly throughout the process while she helped and took the initiative to do things I could not do because I was out of state. I highly recommend Tanya and her team.”
“We were matched up with Greg Maund who was an incredible broker and help us get the apartment of our dreams. ”
“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.”
“Susan was very friendly and helpful in helping us purchase our home. She listened to our needs and worked with us to find the home that best fit our needs. She allowed us time to look and made us aware of any concerns. When we had questions she answered them or pointed us to someone that could.”
“Great Real Estate person you can't do without if you are buying or selling .”
“Angela Mancinone was very knowledgeable about the area and quick to find what would interest us She was always available to answer questions and offer suggestions. Angela was personable as well as professional and did a great job finding us a new home and walking us through the process.”
Information and statistics on the latest trends in the Chesterfield real estate market, updated for September 2025. *
Chesterfield had 3 active listings in August, including 1 new listings. Overall, active listings were down 0.0% from the previous month.
Of those 3 active listings, 33.33% reduced their price in the month of August. The median listing price for homes in Chesterfield grew 256.49% from July to August, bringing the current median listing price to $1,950,000. Based on projected data for September, listing prices may continue to grow.
Chesterfield offers residents a close-knit community with abundant natural beauty, ample outdoor recreation, and a calm, welcoming hometown atmosphere.
Chesterfield rewards those who prize quiet roads, clear night skies, and the kind of community where neighbors still know each other’s names. Outdoor lovers make frequent pilgrimages to the dramatic rock walls and rushing rapids of Chesterfield Gorge, cared for by The Trustees of Reservations, and trace the bends of the federally designated Wild & Scenic Westfield River, a favorite for fishing, paddling, and birding. Historic texture runs deep at the hands-on Bisbee Mill Museum, while literary history is close by at the William Cullen Bryant Homestead. Weekend adventures also extend to the lakes and trails of DAR State Forest in the next town over.
Families appreciate the strong school network: youngsters attend New Hingham Regional Elementary School in town, and older students are part of the Hampshire Regional School District based in nearby Westhampton. Daily conveniences are close, with independent shops and services sprinkled through Williamsburg and quick trips to the dining, arts, and live music scenes of Northampton and Easthampton. Commuters can reach larger employers in Springfield, while life retains the easygoing rhythm that defines Hampshire County.
Whether you’re searching for a sunlit farmhouse near the river or planning to list a hilltop hideaway, Agent Pronto can connect you with a top local real estate pro to navigate the Chesterfield market—tailored to your timing, budget, and goals.
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 Chesterfield 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 Chesterfield. 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 Chesterfield 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 Chesterfield. 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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