“Brandy was fantastic every step of the way and stayed consistent throughout this entire process. Highly recommended for anyone in need of a realtor.”
Century 21 Elite Realty
- Agent Pronto
- New York
- Chester
The best way to find top real estate agents in Chester, NY
Skip the search. We analyze thousands of real estate agents in Chester and nationwide to find you proven local pros, for free.
Compare top Chester real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for March 2026. *
Ammar Iqbal
5.0
(6)
eXp Realty
58 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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Chester real estate Market Report.
Information and statistics on the latest trends in the Chester real estate market, updated for March 2026. *
Chester’s home values have climbed strongly over the past year, rising about 16.2% to a typical value of roughly $412,500. That pace far outstrips Orange County overall, where values are around $440,000 and up a more modest 3.53% year over year. Inventory has also expanded sharply in Chester, up about 120% from last year, signaling more options than buyers saw before.
February 2026 data shows a median list price near $370,000 and just 11 homes on the market, with 5 new listings and 4 pending sales. Homes are taking much longer to sell, with median days on market jumping to 105, an increase of about 138.64% compared with last year and up sharply month over month as well.
Despite slower timelines, conditions still lean toward sellers, reflected in a seller’s market gauge of 28 and an average sale-to-list ratio above 1.04, with half of recent sales closing above asking price. Looking ahead to March 2026, typical values are projected to edge up to about $422,525, and the median list price is expected to move toward $407,500 while inventory holds at roughly 11 homes, suggesting gradually rising prices alongside steady supply. In this evolving environment, both buyers and sellers can benefit from Agent Pronto’s help connecting with a skilled local real estate agent in Chester.
28
Seller’s Market
Seller’s Market
Buyer’s Market
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10
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25
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Chester has to offer.
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.
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“Working with Nicole have been a pleasure. Nicole consistently demonstrates exceptional expertise, integrity, and dedication. Her thoughtfulness, clear communication, and perspective make her an invaluable partner for clients seeking warm and cozy home.”
Century 21 Full Service Realty
“Nael,I would highly recommend him for your real estate agent.He was very professional,knowledgeable,and was exponential in closing our real estate transaction. He was also a really nice guy and relatable THANKS AGAIN NAEL”
CENTURY 21 Elite Realty
“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. ”
Old Towne Living NY Inc.
“She is extremely exceptional 👏 very helpful and nice person.”
Century 21 Elite Realty
“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”
Century 21 Elite Realty
“Virginia worked well with me to sell my home. Communication was easy and she was always on time”
Century 21 Alliance Realty Group
“Sold my house when others couldn't. Sold it fast for asking price. Doesn't get any better than that!”
eXp Realty
“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.”
Grand Lux Realty
“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.”
Coldwell Banker American Homes
“You put me in touch with very good realtors. I chose Rebecca Kane from the recommendations. She did an excellent job.”
Keller Williams Hudson Valley United
“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.”
Keller Williams Realty Hudson Valley North
“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. ”
Better Homes & Gardens Real Estate BHGRE Green Team
“We thought Hermi Aquino was an exceptional realtor—one we recommend to others without hesitation.”
RE/MAX Distinguished Homes & Properties
Frequently Asked Questions
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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.
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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.
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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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