Find the perfect real estate agent in Chesterfield, MA

We analyze top real estate agents in Chesterfield and across the country to find you the most proven local agents, for free.

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Chesterfield, MA real estate

The easiest way to find the best real estate 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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Home buyers and sellers love Agent Pronto.

Here’s what some of the 400,000+ home buyers and sellers have had to say about our service.

“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.”
5 stars
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Frank E.
Springfield, MA
“Agent Pronto connected us with the perfect agent! Extremely professional, knowledgeable, helpful, and prompt to communicate throughout the entire process. Highly recommended!”
5 stars
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Anne F.
Newton, MA
“Great service and Chris Cassidy was professional, courteous, efficient and responsive. I would recommend him to anyone.”
5 stars
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Anne G.
Boston, MA
“Great real estate experience with Charlotte. I recently had the pleasure of working with Charlotte as my realtor, and I cannot express how grateful I am for her outstanding service throughout the entire home buying process. From our initial meeting to the closing day, Charlotte demonstrated a level of professionalism, expertise, and dedication that greatly met my expectations. One of Charlotte's standout qualities is her extensive knowledge of the local real estate market. She took the time to understand my preferences and priorities, providing valuable insights into neighborhoods, property values, and future market trends. Her expertise not only streamlined the decision-making process but also ensured that I made informed choices.”
5 stars
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Kheang T.
Lowell, MA
“We were matched up with Greg Maund who was an incredible broker and help us get the apartment of our dreams. ”
5 stars
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Sharon R.
Boston, MA
“The first day I met Carol to show her the house, she spent a good deal of time checking it out and gave me many tips for improvement, which is exactly what I needed. The listing to closing period was about thirty days, which was also important to me since we were approaching winter, and I did not want to worry about freezing pipes in an empty house. Carol took care of all the important deadline dates. She was personable, competent, and professional in everything she did to sell my house. I did not have any worries due to my confidence in Carol. If I had another house to list, I would call her back tomorrow!”
5 stars
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Sharyn F.
Somerset, MA
“We were given the choice of 2 agents to work with based on the area we were looking to buy. We chose Judy Rivard and are so happy we did. Judy is very professional and definitely looked out for our best interest throughout our home buying process which lasted almost 8 months. She is so knowledgeable and passionate about what she does, we were so happy to have met her.”
5 stars
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Jamie H.
Belchertown, MA
“Trish Marchetti -- the agent we received through you -- was the best!! We would very highly recommend her!!!”
5 stars
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Katherine F.
Franklin, MA
“Tracey is very knowledgeable and guided us through the process. She coordinated all the sales documents and helped out by letting the various groups into the home. We were especially pleased with her efforts and communication to us.”
5 stars
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Barbara K.
Falmouth, MA
“Agent was great, went above and beyond many times. Always helpful, always patient, very knowledgeable. Highly recommend.”
5 stars
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Jan W.
Taunton, MA

Chesterfield real estate Market Report.

Information and statistics on the latest trends in the Chesterfield real estate market, updated for June 2025. *

The median listing price for homes in Chesterfield fell 12.48% from March to April, bringing the current median listing price to $393,850. Based on projected data for May, listing prices may continue to fall.

Chesterfield, MA real estate
20
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Chesterfield has to offer.

Chesterfield offers its residents a charming and serene community filled with natural beauty and outdoor recreational opportunities.

Chesterfield offers a blend of scenic beauty, historic character, and a welcoming sense of community, making it an inviting choice for those seeking a peaceful lifestyle surrounded by natural splendor. This rural town sits on the eastern edge of the Berkshires and features rolling hills, open farmland, and expansive woodlands that attract outdoor enthusiasts year-round. Chesterfield Gorge, a highlight managed by The Trustees of Reservations, draws hikers and sightseers with its dramatic rock formations and the rushing waters of the Westfield River. The Chesterfield Four Seasons Club further enriches local life with community activities and snowmobile trails, making it easy to connect with neighbors.

Families enjoy access to the New Hingham Regional Elementary School, known for its dedicated staff and commitment to fostering vibrant learning. As a member of the Hampshire Regional School District, students progress to strong schools in Hampshire County, with opportunities for art, academic clubs, and athletic programs. Chesterfield’s central location provides access to amenities in Northampton and cultural attractions of the Pioneer Valley, while still maintaining that feeling of rural tranquility.

Rich in history, Chesterfield’s preserved 19th-century architecture, like the Chesterfield Town Hall, and vibrant seasonal events, including the celebrated Chesterfield 4th of July Parade, create strong ties among residents. For those who appreciate close-knit gatherings, locally grown food from Hilltown Community Development’s Hilltown Mobile Market offers fresh produce and a taste of the region’s agricultural heritage.

Agent Pronto is ready to help both buyers and sellers navigate the Chesterfield real estate market, connecting you with expert local agents who understand the area’s unique appeal. Whether you’re searching for a historic farmhouse, an artist’s retreat, or a spacious home with acreage, Chesterfield invites you to become part of its story.

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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!

Sarah W.

Take the guesswork out of finding an agent.

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.

Data analysis with a human touch.

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!


Frequently Asked Questions

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.