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 November 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.
“Working with Nael was a excellent experience from start to finish! He was professional, knowledgeable, and very responsive making the process smooth and clear. We truly appreciate his guidance during this new chapter of our lives. We highly recommend him!”
“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.”
“Vesna was wonderful. She did an amazing job. She is a world class professional. No excuses just results. Long story short God bless me with her. She is simply a legend. Hands-down the best. My words could express how instrumental she was in selling my property. Thank you Vesna!”
“I haven’t even purchased a home with Robert yet, and I can already say without hesitation that he has earned every one of these five stars. When I first started working with Robert, I wasn’t even entirely sure what my next chapter looked like. I went from considering renting, to buying a home, to exploring an income-producing property, and now to seriously considering building my dream home. Through every pivot - and there have been a few - Robert has never made me feel like I was wasting his time or needed to hurry up and make a decision. He has simply met me where I am, answered what feels like a thousand questions, educated me, encouraged me, and helped me think through what makes the most sense for my life and my future. And he has quite literally walked through homes with me and told me, flat out, “Do not buy this house.” That matters to me. Robert is not interested in simply selling me a home so he can collect a commission. He has been very clear that he does not want to be part of the worst financial decision I ever make. He wants to be part of the best one. That means he will point out what I may not see, tell me when something gives him pause, and steer me away from a property if he believes I would regret it later - even if that means we keep looking. I cannot overstate how much trust that builds in a relationship with a real estate agent. What also sets Robert apart for me is his commitment to veterans. Robert is an Army veteran himself, and his knowledge of VA benefits, VA home loans, and the resources available to veterans goes far beyond knowing how to complete a real estate transaction. He genuinely wants veterans to understand and receive the benefits they have earned. In my case, his knowledge of benefits 100% changed my life. During one of our conversations, Robert encouraged me to pursue a VA disability claim for an injury that occurred when I was in service. This wasn’t even something I knew was available to me. He helped me understand that these benefits existed for all veterans- not just those who were injured during deployment or combat. I never knew this as I got out in the early 90’s and this wasn’t explained to veterans then. I followed his advice, filed my claim, and ultimately received a VA disability rating that, without question, changed my life. There was no commission attached to that. No house sale.. Nothing in it for him other than knowing he was helping someone. He simply saw another veteran who might be entitled to benefits she had earned and took the time to point me in the right direction. I will never forget that. Robert is knowledgeable, patient, straightforward, and incredibly generous with his time and expertise. He’s also a family man, and I think that shows in the way he approaches his clients. He doesn’t seem interested in simply putting people in houses. He wants to understand what you are trying to build for yourself and your family, and then help you make the smartest possible decision about how to get there. So yes, someday I fully expect this review will include the story of the house Robert helped me buy or, at this rate, the dream home he helped me build. But he has already helped me with something far bigger than a real estate transaction. If you are a veteran looking to buy a home, particularly someone who isn’t completely sure what benefits or opportunities are available to you, I cannot recommend Robert highly enough. And veteran or not, if you want an agent who will actually listen, educate you, protect your interests, and stay alongside you until the right decision becomes clear, Robert is exactly the kind of person you want in your corner.”
“Responsive, knowledgeable and a wonderful person to deal with! We met Katy when we scheduled a showing through Zillow for a property we were interested in. We were impressed with her responsiveness and knowledge from day one. From representing us in our offer and throughout the entire process to closing, Katy was on top of things and helped move everything along smoothly. We could not have picked a better agent to represent us. Highly recommend her!”
“I worked with Jackie to purchase my first home. I was matched with her randomly through Zillow, and I immediately liked her from our very first appointment. As a first-time homebuyer, I had a lot of questions and took a long time to find the right house. Jackie was incredibly patient throughout the entire process and never made me feel pressured to rush into a decision. She was always honest, clear, and upfront with me about the homes we looked at and the buying process itself. One of the things I appreciated most was that she never pretended every house was amazing or tried to oversell me. I knew my budget was limited, and I didn’t need someone trying to convince me that a house with obvious issues was “perfect.” Some of them really were duds! Instead, she was diplomatic, realistic, and genuinely had my best interests in mind. She also did a great job helping me visualize what was possible in each home. As we walked through houses, she’d point out simple improvements or changes that could make a big difference without requiring a huge renovation. That perspective was incredibly helpful. More than just being a great real estate agent, Jackie became a trusted advisor throughout the process. I always felt like I was getting honest guidance instead of a sales pitch. I feel very lucky that Zillow matched me with her, and I truly enjoyed spending time with her during the search. Buying your first home can be stressful, but having Jackie by my side made the experience so much easier. I would recommend her without hesitation to anyone looking to buy a home.”
“Brandy was fantastic every step of the way and stayed consistent throughout this entire process. Highly recommended for anyone in need of a realtor.”
“Jeffrey did an outstanding job assisting us with finding our dream home. He was consistent, patient, and knowledgeable. We were able to find and close promptly, which was completely pleasing to our family. I definitely recommend working with Jeffrey to help you find your dream home.”
“Michael was great to work with during the home buying process. He kept me informed throughout the process and helped negotiate a prolonged sale that took some unexpected turns. Thank you, Michael!”
“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. ”
“Annette was able to do what I was not! I was out of town and relied on her expertise to find a buyer and close the deal, which she did in a relatively short period of time. I thank God that she was able to help me begin the next chapter in my life.”
“Sold my house when others couldn't. Sold it fast for asking price. Doesn't get any better than that!”
“BEST IN THE TRADE...GOAT. Rebecca Kane is very professional and knowledgeable in the real estate market. She went all out to make sure everything step throughout the process went smoothly. She treated us like FAMILY. EXCELLENT SERVICE!!!!!”
“Brenda did an outstanding job getting us our home. We got our home inspection done right away and were able to close on our new home within 3 weeks. She was knowledgeable and stern when she needed to be. Couldn’t have asked for a better realtor!”
“Working with Michael Levy to sell my Mother’s house, (my childhood home,) was the best decision we made. From his personalized attention and professional recommendations, to his quality vendor relationships and overall knowledge & expertise in the market made for as smooth an experience as possible. We were very grateful in having Michael represent our property and highly recommend working with him as he is someone who cared every step along the process and was there to answer any questions he knew and would research the answers to those he didn’t. Thank you again!”
“Dan was truly amazing throughout the whole process! This was my first home purchase and the process of finding my home and closing was 6 months. Throughout the 6 months, he was professional, patient, honest, responsive and made the process so much easier. He never made me feel rushed and pressured but had a sense of urgency when needed. I truly appreciate all of his work and would not have found my home without him. Thank you!”
“I highly recommend Susan McMullen to anyone in need of an agent. She showed genuine care throughout the entire process of finding an appropriate tenant for my rental apartment. Her dedication, professionalism and expertise put me at ease knowing that the applicants were screened and suited for the basement apartment located in my home. Her friendly approach made my rental experience enjoyable and I will definitely use her service again.”
“I were so fortunate to have found Jason Lysack when I the Lagrange area. As our Realtor, he helped me find the right house in the right neighborhood for the right price. He was patient as I was very excitied but emotional at that time, since i had just lost my husband and mom three months eariler. We looked at homes over two months, almost every day. Jason cautioned me about making unreasonable offers when I fell too quickly for overpriced homes. In short, he was always on my side working to make my house purchase as simple and successful as possible. The best part about working with Jason was that he was always more focused on answering my questions, giving me good advice, and finding homes that met my needs than he was on closing a deal. We would recommend him to anyone. I am so happy now, thanks to Jason !!!!!”
“Working with Connor was an absolute pleasure from start to finish. This was our third time working with him, but this time around we were navigating uncharted waters, as we were in a completely different state and looking to purchase in NJ. Connor's expertise, professionalism, and unwavering support made the entire process smooth and stress-free for us! Connor always takes the time to understand our needs, preferences, and budget. He listened attentively to our concerns and patiently answered all our questions, providing valuable insights and guidance every step of the way. Connor's knowledge of the market is always truly impressive. He was proactive in presenting us with a variety of options that aligned perfectly with our criteria, and his keen eye for detail helped us identify properties that we might have overlooked otherwise. What sets Connor apart in general is his genuine commitment to his clients' satisfaction. Connor went above and beyond to help us throughout the home buying process by being available to act on our behalf during inspections, securing quotes for necessary work and keeping us completely up to date on our new home. We had some very unexpected things pop up during our contract period and Connor was always available to jump in to handle since we were so far away and that is true dedication. We couldn't be happier with the outcome of securing this wonderful home and that is in huge part to Connor for making it a reality. If you're in the market for a top-notch realtor who truly cares about his clients and delivers results, look no further than Connor. He's a true professional in every sense of the word, and we can't recommend him highly enough for whether you are looking to purchase a home or sell your home.”
“Nerette is wonderful! I met her by chance when I was first starting to think about purchasing a second home and I couldn't be happier that I did. She was super sweet, patient, personable and knowledgeable. When I finally found my dream home, she saw me through the entire process explaining everything along the way. Nerette is a lovely person inside and out who is trustworthy, honest and by the book. I highly recommend her to help you find the home you've been looking for. Thank you so much Nerette for everything. You are a true gem!”
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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