We analyze thousands of real estate agents in Chester and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for June 2026. *
* 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.
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Information and statistics on the latest trends in the Chester real estate market. *
Feb 1, 2026 - Apr 30, 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 (Feb 2026 - Apr 2026).
Year over year in Chester, typical home values in this rolling three-month view are down, with the median sale price falling more than 13 percent. At the same time, inventory has expanded sharply, as active listings are up about 77 percent compared with a year ago. New listings are also surging, rising more than 150 percent year over year and giving buyers more choices than they had last spring.
Looking at the latest rolling period ending in April 2026, the median home value sits around $320,000, while the median list price is notably higher at about $427,000. Homes are spending a median of 27 days on the market, and months of supply has grown to 3.7, signaling more balance than in past periods.
Even with this added supply, competition has not disappeared. More than half of recent sales closed above the asking price, and the average sale-to-list ratio is just over 101 percent, indicating many sellers are still achieving slightly more than they ask. Closed sales and pending contracts have both inched higher compared with last year, suggesting steady demand as listings increase. With conditions shifting but still favorable to sellers in many cases, buyers and sellers in Chester can both benefit from an Agent Pronto–recommended real estate agent to help them navigate pricing, timing, and negotiation in today’s market.
Chester offers residents a welcoming, close-knit community with ample parks and outdoor spaces, convenient local services, good schools, and engaging neighborhood events that foster connection and a high quality of life.
Chester offers a small-town feel that stands apart from nearby Middletown and Newburgh, with a quieter pace and strong sense of local pride. Set amid rolling hills and farmland, it balances country scenery with everyday conveniences and an easy drive to Orange County job centers and New York City commuter routes.
Residents value the historic Main Street district, seasonal events, and community traditions. The expansive Goosepond Mountain State Park provides hiking and wildlife viewing, while the Heritage Trail gives walkers and cyclists a paved path that links Chester to Monroe and Goshen. Families often gather at Chester Commons Park for concerts, playground time, and town celebrations.
Local dining spots such as Rustic Wheelhouse and the classic Glenmere Mansion restaurant in nearby Florida add to the area’s appeal, while the Chester Union Free School District is a key draw for households planning the long term. Everyday shopping and services are close at hand, and larger retail options in Monroe and Warwick are within a short drive.
Whether you are preparing to list your home or hoping to secure the right property in a competitive market, timing and preparation are critical in Chester. Agent Pronto can connect both buyers and sellers with an agent who understands the community and its trends.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Nael Dassan was exceptional with his knowledge,professionalism,attention paid to his costumer.Lew and I would highly recommend Nael as anyone's real estate broker .Nael shows understanding and compassion whether he is dealing with with a high stakes sale or a average sale .Everyone who comes across Nael is treated with respect as he applies his professional approach. Thank you Nael respectfully Lew and Terri MacBrien 6/2026”
“Después de una larga jornada para lograr comprar nuestra casa, por fin hemos llegado a la meta. 🏡 Queremos agradecer a María de Osorio por su apoyo durante todo este proceso. Siempre estuvo disponible para responder nuestras dudas y preguntas, brindándonos orientación y tranquilidad en cada paso. Definitivamente la recomendaremos a nuestros amigos y familiares. ¡Gracias por ayudarnos a hacer realidad este sueño!”
“Working with Nicole Issac was an absolute pleasure from start to finish. She was outstanding in every aspect of the process and truly went above and beyond to help us secure our property. Her patience, professionalism, and dedication made what could have been a stressful experience feel smooth and manageable. Nicole took the time to answer every question, explain every detail, and guide us through each step with confidence and care. No matter how many concerns or requests we had, she remained calm, responsive, and supportive throughout the entire journey. Her knowledge of the market, attention to detail, and commitment to our needs were exceptional. We always felt like a priority, and it was clear that she genuinely cared about helping us find the right home. I would highly recommend Nicole Issac to anyone looking for a trustworthy, hardworking, and patient real estate agent. She exceeded our expectations in every way, and we are incredibly grateful for all of her help.”
“Brandy was fantastic every step of the way and stayed consistent throughout this entire process. Highly recommended for anyone in need of a realtor.”
“I am glad that I contacted Agent Pronto, so I got to connect with Martha Gaffney. It has been a great pleasure working with her and she worked really hard to get me a house which is well worth it. Thanks Martha and thanks Agent Pronto for the opportunity. ”
“Vesna is a top notch Broker and will always stick to her in the future and will also recommend her to anyone who needs real estate broker”
“Virginia worked well with me to sell my home. Communication was easy and she was always on time”
“Sold my house when others couldn't. Sold it fast for asking price. Doesn't get any better than that!”
“I enjoyed the extra mile as well as ear. Positive when needed, clarity when asked. Imelda's professionalism and experience provided great value and insight, when a smooth situation became more challenging. Imelda has experience that was significan to me, I don't think I would've done this without you. Thank you.”
“Matthew is very knowledgeable as a broker, He told us what to expect and what needed to be done to get the most of what we were asking for. He guided us every step of the way and made me feel comfortable through the process. He is very reliable and always kept me informed throughout the sale of the house. I would highly recommend him him to all my friends and will use him in the future for the purchase of my second home. I can definitely say he is a great asset to your company.”
“You put me in touch with very good realtors. I chose Rebecca Kane from the recommendations. She did an excellent job.”
“Travis is the best. He loves his job.”
“Arleen was pleasant, knowledgeable, and proactive. I enjoyed working with Arleen. She did things the way I would have. She was direct, patient to a point, and professional. The process did not lag on Arleen's watch. Highly recommend.”
“Patrick Taylor made the task of selling my home painless. He kept me informed through the entire process and I would recommend him to anyone trying to buy/sell their home. ”
“We thought Hermi Aquino was an exceptional realtor—one we recommend to others without hesitation.”
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.
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