“Nicole is very professional, polite and knowledgeable. She's passionate about her work, and very patient. I will work with her again for sure.”
Century 21 Full Service Realty
- Agent Pronto
- New York
- Chester
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for September 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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Chester real estate Market Report.
Information and statistics on the latest trends in the Chester real estate market. *
Latest Rolling 3-Month Snapshot
Jun 1, 2026 - Aug 31, 2026
Median sale price
$348K
+15%
from Q2 '26
Median list price
$363K
-24%
from Q2 '26
Active listings
37
+23%
from Q2 '26
Homes sold
11
+10%
from Q2 '26
New pendings
12
-7.7%
from Q2 '26
New listings
24
+60%
from Q2 '26
Quarterly Pricing Trends for Chester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Chester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Chester
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Chester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Chester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Chester
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
31
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jun 2026 - Aug 2026).
Over the latest rolling three-month window through August 2026, Chester’s home values have eased compared with a year ago. The typical home value is down about 8 percent year over year, even as prices have ticked up in recent months. At the same time, inventory has grown sharply, with active listings up about 70 percent from a year earlier and months of supply more than tripling.
Conditions on the ground now reflect a market with more options and a bit more breathing room. Homes are taking longer to sell, with median days on market up 16 percent year over year to about a month and a half, and only about 36 percent of recent sales closed above list price compared with much higher shares in 2023.
Looking at the latest period, typical home values and median list prices sit in the mid-$300,000s, while the sale-to-list price ratio hovers just under 100 percent, suggesting buyers still need to write solid offers even with more choices. New listings and homes sold are both slightly higher than a year ago, indicating steady activity despite the cooler pricing environment. With the market gauge still pointing to seller-leaning conditions but far looser than in past years, both buyers and sellers in Chester can benefit from an Agent Pronto–recommended real estate agent who understands these shifting dynamics and can guide them through their next move.
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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“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!”
CENTURY 21 Elite Realty
“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!”
Century 21 Elite Realty
“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
“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.
“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.”
EXP 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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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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