We analyze top real estate agents in Chester 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 August 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.
We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent.
“Lisa Caron knows her market, is direct and to the point with suggestions about ways to improve the look of the property for showings and was always available whenever I needed her for some question or concern I had. I highly recommend her to anyone either buying or selling real estate.”
“Sheri was incredibly knowledgeable, patient, and helpful throughout the process of buying our first home. Had great attention to detail and pointed out things we hadn’t even considered. We would highly recommend Sheri!”
“I met Spencer through one of his other endeavors- as building manager for my apartment. I found him to be a responsive and helpful manager. I was very happy with his work, but I didn't really know anything about him other than that. One day, a "for sale" sign appeared outside of the building next-door with Spencer's name on it. Can't forget a name like that. I asked Spencer lots of questions and even though I wasn't ready to buy, he took the time to talk about what purchasing a home would look like. Over time, I decided I wanted to invest as an owner-occupier of a multi family home in the area. When I was ready to shop, Spencer outdid himself. He worked with my schedule and I saw multiple properties. As we looked at different buildings, Spencer was able to help me focus in on what I truly wanted in a home as well as what I could afford. I learned so much! With Spencer's continued support and encouragement, I found a great 3-decker. He is a wonderful realtor - and also a new friend!”
“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.”
“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.”
“I cannot say enough positive about my experience working with Kurt. Kurt is honest, smart, personable, patient, knowledgeable, hard working, a great communicator, and professional. He has a way of explaining everything extremely well, and was always able to keep me calm when things appeared to be chaotic. I would recommend Kurt and his team in a heartbeat.”
“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.”
“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 am very please with Isadora professionalism and her friendly demeanor. Isadora made the process easy. Though, the property was occupied with tenants. She explained the process and she delivered,. The house was sold quickly.. I am still smiling. I will be smiling for years to come. If you are looking for a professionalism and trustworthy realtor choose Isadora Sarto..”
“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.”
“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!”
“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 .”
“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 Chester real estate market, updated for August 2025. *
Chester had 2 new listings and 1 listings that went under contract in July, decreasing the area’s total available inventory to 5—down 37.5% from the previous month. Inventory is projected to have further decreased in August.
The median listing price for homes in Chester fell 44.0% from June to July, bringing the current median listing price to $279,950. Based on projected data for August, listing prices may continue to fall.
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 tight-knit community, scenic landscapes, and ample opportunities for outdoor recreation and civic engagement that together support a high quality of life.
Chester is a small mountain-river town with outsized character, set along the wild Westfield River in Hampden County and serving as a quiet gateway to the highlands of Berkshire County. Outdoor lovers find endless reasons to explore: the dramatic stonework of the Keystone Arches and the cascades of Sanderson Brook Falls are highlights of the expansive Chester-Blandford State Forest, managed by the state’s parks agency for hiking, fishing, snowshoeing, and leaf-peeping throughout the year. Discover trail maps, picnic areas, and seasonal updates through the forest’s official page at the state Department of Conservation and Recreation.
Arts and history thrive here, too. The acclaimed Chester Theatre Company stages thought-provoking summer productions in an intimate setting, drawing audiences from across the region. Railroad heritage runs deep at the historic depot and museum, and the town’s annual rail-themed festivities celebrate the engineering that carved a route through this rugged valley.
Families are served by the Gateway Regional School District, which offers strong academics, arts, and athletics across its member towns. Everyday conveniences are close by, with roughly 30 minutes to Westfield and under an hour to Springfield for major employers, universities, and medical centers—while home remains wonderfully peaceful at day’s end.
Whether you’re searching for a hillside retreat or preparing to list your current place, Agent Pronto can connect you with a trusted local real estate professional who knows Chester inside and out.
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 Chester 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 Chester. 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 Chester 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.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents.
We can help you find the perfect real estate agent just about anywhere.
