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 April 2026. *
57 recent sales
$250K-$1.38M price range
$440K median price
* 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, updated for April 2026. *
Chester home values have shifted notably over the past year, with the typical home value down about 15.23 percent. Inventory has grown sharply year over year, up 225 percent, while pending sales doubled in the same period. New listings also climbed 75 percent, signaling more homeowners are bringing properties to market compared with last year.
Looking at March 2026, the typical home value in Chester was about $320,000, while the median list price was higher at roughly $450,000, showing that asking prices sit above the broader value benchmark. Homes moved quickly with a median of just 16 days on market, down about 63.64 percent from a year earlier and 84.76 percent from the prior month, and months of supply stood at a relatively lean 2.6.
Only 23.08 percent of listings saw a price drop, yet around 60 percent of homes still sold above their list price, and the average sale-to-list ratio was about 0.968, all supporting Chester’s classification as a seller's market with a market gauge of 22. Looking ahead to April 2026, projections point to a typical home value near $273,750, a median list price around $493,550, and inventory edging up to about 14 homes, while nearby Orange County sits higher with a typical value around $460,000 projected to reach $470,000 and 782 homes on the market. Buyers and sellers in Chester can both benefit from these detailed trends, and Agent Pronto can help each of them find a local agent who understands this evolving market.
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 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.
“Nicole is an exceptional real estate agent. She truly understood our needs and consistently recommended homes that aligned perfectly with what we were looking for. She was always punctual, professional, and offered thoughtful, insightful advice throughout the process. Thank you, Nicole!”
“Nael was proficient in the general marketing area of homes and expectations of sales in the broader area. He was positive, pretty receptive and had a friendly personality. He was great to deal with and showed a substantial level of kindness and compassion during the sale of my once dream home. It was an emotional roller coaster and thanks to Nael and Venza, it was a bit easier on my breaking heart.”
“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. ”
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“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!”
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“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.”
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“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.
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