We analyze thousands of real estate agents in Chestertown 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 June 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 Chestertown real estate market. *
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 (Q4 2025).
Chestertown currently leans toward sellers, with the market gauge signaling a seller’s market. Only four active listings are available in the latest rolling three-month period. Limited supply is a key factor behind this seller-friendly reading.
Prices have been moving sharply higher over the past year in this rolling three-month view. The median list price is about $337,000, up more than 60 percent compared with a year earlier. Recent sale prices also show sizable growth, rising from around $223,000 at the end of 2023 to roughly $272,500 by late 2024.
Inventory has tightened notably over time, dropping from around nine to eleven active listings in mid-2024 and 2025 to just four now. New listings are also down more than 40 percent year over year in the latest period, which can make it harder for buyers to find options. At the same time, months of supply has swung widely in the past couple of years, reflecting a small market where each new listing or sale can shift conditions. With prices trending higher and choices limited, buyers and sellers in Chestertown can both benefit from Agent Pronto’s help in finding an experienced local agent to guide their next move.
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.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“100% recommend our realtor Nael! 36 hours from signing the listing agreement to receiving a serious offer from a quality buyer, ready to close within a month on our parent's home in Hartsdale, NY. It doesn't get any better than that! Nael excelled in all aspects of the sale process. He set clear expectations up front and communicated effectively every step of the way. Thank you Nael for everything 🙏”
“Ricky's experience in the local area, hard-working attitude and positive demeanor make him a great choice for perspective buyers in the Watetown/Fort Drum area!”
“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!”
“Working with Nicole Issac was an absolute pleasure from start to finish. She was outstanding in every aspect of the process and truly went above and beyond to help us secure our property. Her patience, professionalism, and dedication made what could have been a stressful experience feel smooth and manageable. Nicole took the time to answer every question, explain every detail, and guide us through each step with confidence and care. No matter how many concerns or requests we had, she remained calm, responsive, and supportive throughout the entire journey. Her knowledge of the market, attention to detail, and commitment to our needs were exceptional. We always felt like a priority, and it was clear that she genuinely cared about helping us find the right home. I would highly recommend Nicole Issac to anyone looking for a trustworthy, hardworking, and patient real estate agent. She exceeded our expectations in every way, and we are incredibly grateful for all of her help.”
“It was a pleasure to work with Crystal. She was knowledgeable and very responsive to requests. She shared updates as they occurred and came to our home for most of the paperwork signings. From listing to closing it was about 5 weeks to sell our property with 8 offers the first week! Thank you to Crystal the whole process went smoothly. We are very happy. We would list with her again in the future. Thank you. L”
“Claudia was nothing short of amazing to work with during the process of looking for our first home. The whole process was made so much easier knowing we had someone like Claudia looking out for our best interests. She was always available to answer questions, offer guidance, and let us know when something that fit out criteria was available to visit. I would recommend Claudia without hesitation to anybody looking for a real estate agent.”
“I had an incredible experience working with Samuel Okine for my first NYC apartment. From start to finish, he was attentive, knowledgeable, and genuinely invested in helping me find the perfect place. Sam's guidance made the entire process stress-free, and I couldn't be happier with my new home. I highly recommend Sam to anyone looking for a trustworthy and professional agent in New York City!”
“A true professional. Alana is great at what she does .”
“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. ”
“I have never seen a realtor agent go above and beyond like Sandy. I willl never work with another agent other than Sandy in the future”
“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”
“My realtor was incredible and very helpful throughout the process of selling my home.”
“We were referred to the Carrillo Agency and worked with Brandi Everett. She was great helping us through the entire buying process. She made sure we were covered by a colleague when she couldn't be there and guided us through the search, bidding and closing process. We can't thank Brandi enough for her help.”
“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.”
“Happy to find an agent who was familiar with multi-family across the nation for my purchase.”
“Kevin was very professional and knowledged. He assisted me so much throughout this stressful buying process and worked in any way possible to decrease the load on my shoulders. I would recommend Kevin to my family and friends.”
“On a whim, I used Agent Pronto, as I was in the market to sell my current apartment. I was connected with Joana Chu, a highly recommended realtor and it turned out to be one of the best decisions I have made.”
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.
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 Chestertown Realtor® or real estate agent today.
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