“I cannot say enough wonderful things about Mary! As a first time homebuyer, I was nervous and overwhelmed going into the process, but Mary made the entire experience so much easier and less intimidating. From start to finish, she provided incredible guidance, answered all of my questions, and always made sure I felt confident in my decisions. Her knowledge, patience, and dedication truly made all the difference. Even when we faced unexpected obstacles along the way, Mary went above and beyond to help navigate them and ensure everything came together. She genuinely cares about her clients and always had my best interests at heart. I am so grateful to have had Mary by my side throughout such an important milestone in my life. I couldn’t have asked for a better realtor and would highly recommend her to anyone looking to buy or sell a home!”
- Agent Pronto
- New York
- Chestertown
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Compare top Chestertown real estate agents.
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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Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
- Tell us what you need.
- Answer a few quick questions about your real estate goals.
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- We’ll find you top local agents based on performance, expertise, and customer reviews.
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Chestertown real estate Market Report.
Information and statistics on the latest trends in the Chestertown real estate market. *
Quarterly Pricing Trends for Chestertown
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Chestertown
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Chestertown
Rolling three-month data ending on quarter boundaries when available.
Quarterly Inventory and Sales Activity for Chestertown
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Chestertown
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Chestertown
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).
Chestertown currently leans toward sellers, with the market gauge at 30, but conditions are not overly heated. Months of supply sit high at 9.6, pointing to more options for buyers than in a tight seller’s market. Homes are taking a median of 105 days to sell in this rolling three-month view, which gives buyers additional time to make decisions.
Prices have shifted noticeably over the past year. The typical home value over the latest three months is up sharply, rising about 86 percent year over year, even as the median list price is only modestly higher than a year ago. At the same time, the average sale-to-list ratio is about 96 percent and none of the recent sales closed above asking, suggesting sellers often accept some negotiation.
Inventory and activity patterns help explain the mixed signals. Active listings are slightly lower than a year ago, yet months of supply have nearly tripled over that time, and new listings have more than doubled, indicating slower turnover rather than a lack of homes coming to market. Pending sales are down compared with a year earlier, while only two homes sold in the latest period, highlighting the influence of small numbers on local statistics. Both buyers and sellers can benefit from an Agent Pronto–recommended agent who understands these dynamics and can guide them through Chestertown’s shifting conditions.
Learn more about what Chestertown has to offer.
Chestertown offers residents a welcoming, tight-knit community, abundant outdoor recreation, and a balanced mix of hometown charm with convenient local services.
Chestertown immediately feels distinct from larger Adirondack communities like Lake George or Queensbury. It offers everyday practicality along with easy access to lakes, mountains, and four-season recreation, without the constant tourist traffic that defines many nearby destinations.
The community centers around Main Street, where you will find local fixtures such as The Crossroads and small eateries that anchor daily life. Public amenities like the Chester-Horicon Health Center and the Town of Chester Municipal Center support a year-round population that values stability, neighborly support, and local decision making. Families appreciate access to North Warren Central School, which serves students from elementary through high school.
Outdoor life is a major draw. Residents enjoy Loon Lake for boating and paddling, and the nearby Schroon River for fishing and quiet exploration. Local parks and trails maintained by the Town of Chester Parks and Recreation department make it easy to get outside without a long drive.
In Chestertown, homes range from classic camps and seasonal retreats to full-time residences. Whether you are preparing to list a lake house or time a move into your first Adirondack home, the right local agent can help you navigate inventory, seasonality, and pricing. Agent Pronto connects both buyers and sellers with agents who understand Chestertown’s unique market rhythms.
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“Greg did an amazing job for me. We looked at any house I sent his way and eventually found "The One" he knew exactly what to do and when in order to ensure I was able to get it.”
“Rachel was an absolute pleasure to work with!! She was professional through every part of the process. As first time homebuyers, we could always rely on her to clear things up.”
“Alex was amazing and super helpful in assisting me with my first house purchase. I came in with little to no knowledge and left owning a house that I really love!”
“My wife and I met Colleen eight years ago when we were buying our first house. She helped us every step of the way and when we had issues last minute with our bank she was able to get us on to the help we needed. So when we decided to sell that same house eight years later we knew exactly who we were going to use as our agent. She is professional, knowledgeable, very efficient and really works in your best interest. She cares and it shows. Highly recommend Colleen.”
“This was my second time working with Nathan and each time has been a delight! He is on time for appointments, responds promptly to requests for showings, and proactively marketed our home to achieve a high level of interest on home buying platforms. We had over a dozen showings scheduled in the first day of listing and received multiple competitive offers and an accepted offer within 48 hours of listing. In addition, Nathan is kind and professional and is exactly the pro you want working for you in this process! I highly recommend Nathan as a trusted real estate advisor for your upcoming purchase or sale.”
“Alexis was amazing right from the start. She answered every question I threw at her and even pointed out things I didn’t think to ask about. Her timeliness for responses was impressive. Friendly, knowledgeable and responsive; all around great experience!”
“Ryan was fantastic and helped us navigate the process with grace. As new home owners, we were worried about all the work that goes into buying a house, but with Ryan’s help, the process was quick and easy!”
“Angela did an incredible job helping my husband and I navigate through first time home buying. She is extremely responsive, goes above and beyond to get answers, and has a ton of knowledge on the area.”
“If you’re looking for a real estate agent that is professional, knowledgeable, responsive, patient, and caring, Chris is who you want. From the beginning, Chris was positive and welcoming and I felt my business was appreciated. Chris answered any and all of my questions immediately. He is great at explaining things and extremely patient. We had some hurdles (out of our control), but he was very reassuring. Real estate transactions can be very stressful, especially when things are moving quickly. I’m glad I had Chris as an agent, he helped me not to panic and I was able to take it easy and not worry. I highly recommend Chris, he is top notch! Thanks a million, Chris!”
“Rachel has been very helpful, even when we had an issue after closing. It was such a challenge to buy a house, not living in the area, but we put our trust in her to help us. She has a lot of knowledge of the school districts, pros and cons of locations, and a good understanding of the math involved with offers.”
“Caroline is one of the most diligent, caring, understanding and always has her clients topmost interest in finding the right property!! It was my WIN FOR HAVING HER AS MY REAL ESTATE AGENT considering I was moving here from North Carolina!! NOBODY BETTER She even helped me move in! TOP THAT ONE ??”
“We have been working with Monika since last fall. She’s helped us with a rental and now our dream home! She is patient, responsive, knowledgeable, attentive and caring. She has become a very good friend through the process, and we are so grateful to have worked with her. ??”
“Denise was a pleasure to work with. Very reliable and knowledgable. I would recommend her to anyone. She answered all my question and responded quickly when needed.”
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 Chestertown. 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 Chestertown Realtor® or real estate agent today.
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