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 October 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. *
Jul 1, 2026 - Sep 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 (Jul 2026 - Sep 2026).
Year-over-year trends in Chester show a market that has cooled from last year’s intensity while holding values relatively steady. The typical home value in the latest rolling three-month period is up only about 1 percent from a year ago, even as the share of homes selling above list dropped from roughly 73 percent to about 45 percent. Inventory has expanded sharply over the year, with active listings up about 92 percent and months of supply climbing from around 3.1 to 5, giving buyers more options than they had last fall.
Looking at the most recent rolling three-month window ending in September 2026, conditions reflect this shift toward better balance. Homes are taking longer to sell, with median days on market rising from 33 a year ago to 46, while the average sale-to-list price ratio is just under 100 percent, indicating sellers are still achieving near-full asking prices.
Buyer activity has held up despite the added inventory, as homes sold increased slightly year over year and pending sales rose by about 43 percent, suggesting steady demand. New listings have more than doubled compared with last year’s same period, which helps explain the sizable jump in available homes and supply. With more choices for buyers but still-solid pricing power for sellers, both sides can benefit from knowledgeable guidance, and Agent Pronto can connect buyers and sellers in Chester with an agent who understands these evolving conditions.
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.
“Yo gilberto amaya y familia estamos totalmente satisfechos con la ayuda de Maria de osario es muy profesional y excellent servicio. Yo le doy 10 de 10 x su excelencia. Todo aquel que quiera saber sobre su servicio yo como realtor tenga por seguro q quedara feliz y satisfechos con ella.”
“Nicole Isaacs helped my wife and I purchase our first home. I work in construction project management so a lot of what was involved and the overall pace of the process felt very familiar to me however there were a few curve balls thrown at us that I was unprepared for and Nicole used her channels to keep the negotiations on track to salvage the deal, especially important when we were feeling panicked. She ensured that all relevant parties were kept in the loop at the appropriate times, something I was trying to do myself but dropped the ball on a few times, and she was right there to keep the process moving without us even having to ask. We feel very lucky to have met Nicole and will be reaching out to her the next time we need to buy or sell, and will be enthusiastically recommending her to friends and family in the area.”
“LISTEN TO ME CLOSELY! If you want a 1 stop shop realty company with world class customer service. Don't trust anyone else to represent you and your property. Vesna has been a pleasure to work with from day 1. She has all the experience and resources to deal with the challenges of selling realty property. I can't say enough about her because she is a remarkable person. Vesna is the BEST in the business! Thank you so much!”
“If I could rate Nael Dassan 10 stars out of 5- I would. Never have I met such a high level of professionalism, dedication, strategic thinking and incredible execution. Nael Dassan is the wizard of making real estate dreams come true. I cannot recommend him enough!”
“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. ”
“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.”
“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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