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Chestertown, NY real estate

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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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 Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $319K Median sale price in Jan 2022 - Mar 2022: $175K Median sale price in Apr 2022 - Jun 2022: $275K Median sale price in Oct 2022 - Dec 2022: $206K Median sale price in Apr 2023 - Jun 2023: $273K Median sale price in Jul 2023 - Sep 2023: $338K Median sale price in Oct 2023 - Dec 2023: $223K Median sale price in Jan 2024 - Mar 2024: $295K Median sale price in Apr 2024 - Jun 2024: $460K Median sale price in Jul 2024 - Sep 2024: $395K Median sale price in Oct 2024 - Dec 2024: $273K Median sale price in Jan 2025 - Mar 2025: $180K Median sale price in Apr 2025 - Jun 2025: $135K Median sale price in Jul 2025 - Sep 2025: $213K Median sale price in Oct 2025 - Dec 2025: $265K Median sale price in Jul 2026 - Sep 2026: $395K Median list price in Oct 2021 - Dec 2021: $402K Median list price in Apr 2022 - Jun 2022: $499K Median list price in Oct 2022 - Dec 2022: $224K Median list price in Jan 2023 - Mar 2023: $359K Median list price in Apr 2023 - Jun 2023: $310K Median list price in Jul 2023 - Sep 2023: $312K Median list price in Oct 2023 - Dec 2023: $275K Median list price in Apr 2024 - Jun 2024: $400K Median list price in Jul 2024 - Sep 2024: $370K Median list price in Oct 2024 - Dec 2024: $224K Median list price in Jan 2025 - Mar 2025: $165K Median list price in Apr 2025 - Jun 2025: $229K Median list price in Jul 2025 - Sep 2025: $274K Median list price in Apr 2026 - Jun 2026: $219K Median list price in Jul 2026 - Sep 2026: $287K Oct 2021 - Dec 2021 Median sale price $319K Median list price $402K Jan 2022 - Mar 2022 Median sale price $175K Median list price Unknown Apr 2022 - Jun 2022 Median sale price $275K Median list price $499K Jul 2022 - Sep 2022 Median sale price Unknown Median list price Unknown Oct 2022 - Dec 2022 Median sale price $206K Median list price $224K Jan 2023 - Mar 2023 Median sale price Unknown Median list price $359K Apr 2023 - Jun 2023 Median sale price $273K Median list price $310K Jul 2023 - Sep 2023 Median sale price $338K Median list price $312K Oct 2023 - Dec 2023 Median sale price $223K Median list price $275K Jan 2024 - Mar 2024 Median sale price $295K Median list price Unknown Apr 2024 - Jun 2024 Median sale price $460K Median list price $400K Jul 2024 - Sep 2024 Median sale price $395K Median list price $370K Oct 2024 - Dec 2024 Median sale price $273K Median list price $224K Jan 2025 - Mar 2025 Median sale price $180K Median list price $165K Apr 2025 - Jun 2025 Median sale price $135K Median list price $229K Jul 2025 - Sep 2025 Median sale price $213K Median list price $274K Oct 2025 - Dec 2025 Median sale price $265K Median list price Unknown Jan 2026 - Mar 2026 Median sale price Unknown Median list price Unknown Apr 2026 - Jun 2026 Median sale price Unknown Median list price $219K Jul 2026 - Sep 2026 Median sale price $395K Median list price $287K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
30
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

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.

Find your Chestertown real estate agent today →


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“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!”

Tessa Hughes ·

Photo of Mary Canova
Gabler Realty
“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.”

Doug Eaton ·

Photo of Greg Wakeman
ERA Real Estate Hunt Real Estate ERA
“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.”

astanton16123 ·

Photo of The Lisa Grassi-Bender Team
HUNT REAL ESTATE ERA
“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!”

eric ramsey39 ·

Photo of Capital Region Team at Compass
Compass Greater NY LLC
“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.”

Brendan Purcell ·

Photo of Colleen Cameron
Cartier Real Estate Group
“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.”

amyhollan0601 ·

Photo of Nathan Fox
Berkshire Hathaway HomeServices Zambito Realtors
“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!”

user6914935 ·

Photo of Alexis Madden
Romeo Team Realty
“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!”

Brenna Hull ·

Photo of Mike Castellano
Gilcrest Properties
“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.”

srhdvrs ·

Photo of Angela Dross
Julie & Co. Realty
“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!”

Shaakima Smith ·

Photo of Christopher Serra
Coldwell Banker Prime Properties
“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.”

Jonathan Davis ·

Photo of Scott Varley Team
Keller Williams
“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 ??”

carol knittel ·

Photo of Caroline Baker
Coldwell Banker Prime Properties
“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. ??”

ncsmnmjea ·

Photo of Monika Cronin
Compass Greater NY LLC
“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.”

bdoscher14 ·

Photo of Denise Mosono Allen
HUNT REAL ESTATE ERA

Frequently Asked Questions

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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