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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 October 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 can’t say enough great things about Nael! From start to finish, he went above and beyond to make the entire home-buying process as smooth as possible. His professionalism, knowledge, communication, and dedication truly set him apart. What I appreciated most was his honesty, patience, and willingness to always go the extra mile. No matter what challenges came up, Nael was always available, proactive, and committed to making sure everything was handled the right way. He genuinely cares about his clients and treats the process as if he were buying the home himself. Buying a home is a major decision, and having someone you can trust makes all the difference. I’m extremely grateful for everything Nael did and would highly recommend him to anyone looking to buy or sell a home. You won’t find a better realtor!”

Khaled Dassan · Monroe, NY

Photo of Nael Dassan
CENTURY 21 Elite Realty
“Yo gilberto amaya y familia estamos totalmente satisfechos con la ayuda de Maria de osario es muy profesional y excellent servicio. Yo le doy 10 de 10 x su excelencia. Todo aquel que quiera saber sobre su servicio yo como realtor tenga por seguro q quedara feliz y satisfechos con ella.”

Gilberto Amaya · Middletown, NY

Photo of Maria Morales de Osorio
Century 21 Elite Realty
“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.”

Curtis · Tuxedo Park, NY

Photo of Nicole Isaacs
Century 21 Full Service Realty
“LISTEN TO ME CLOSELY! If you want a 1 stop shop realty company with world class customer service. Don't trust anyone else to represent you and your property. Vesna has been a pleasure to work with from day 1. She has all the experience and resources to deal with the challenges of selling realty property. I can't say enough about her because she is a remarkable person. Vesna is the BEST in the business! Thank you so much!”

Victor Pena · New Rochelle, NY

Photo of Vesna Kanacki
Century 21 Elite Realty
“I would highly recommend Crystal Babcock for any real estate need! She communicated with me throuh every step of the purchase process - and always explained things to me so that I would understand. She was a pleasure to work with and I will definitely use her again, when the need arises.”

Missi McCloskey · Sayre, PA

Photo of Crystal Babcock
Century 21 Jackson Real Estate
“Dependable, knowledgeable, friendly, honest, and overall - EXCELLENT!”

Mark Redder · Pamelia, NY

Photo of Rick Gates
eXp Realty
“Helped me with coop purchase. Very knowledgable, and professional . Highly recommend.”

Vlad Dorfman · Brooklyn, NY

Photo of Lenny Sklyar
RE/MAX Edge
“Working with Claudia Miller was an absolute pleasure. Selling a home—especially while coordinating a major out-of-state relocation—can be a highly stressful experience, but Claudia made the entire process remarkably seamless. She successfully sold my property and did a phenomenal job of setting clear, realistic expectations right from the start. From navigating the initial property disclosures to finalizing the sales contract, her professionalism, transparency, and expertise were evident at every step. I highly recommend Claudia to anyone looking for a top-tier real estate professional.”

Dan · White Plains, NY

Photo of Claudia Miller
Century 21 Elite Realty
“Sandy's communication and negotiating skills benefited us immensely when buying our home in this competitive market. She is so professional and truly knowledgeable about so much. We are recommending Sandy to all of our family and friends.”

Karla Galindo · New Haven, CT

Photo of Sandy Chang
Century 21 Scala Group
“Orly was wonderful from the first phone call to the endless house appointments we scheduled and attended. She never stopped helping me find my perfect home and take in my thoughts, concerns and likes. She was there every step of the way from viewing, inspection, maintenance and repairs, familiarizing with previous owner all the house details, to closing. I never felt like I was bothering her or obligated to make a house purchase I did not want and she never tried to sell me any home I did not want. She was the best!!!!”

Armando Arellano · Port Chester, NY

Photo of Orly Martinez
Keller Williams Realty Group
“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!”

Carolyn · New York, NY

Photo of Samuel Okine
The Agency Real Estate
“A true professional. Alana is great at what she does .”

Brett Paradiso · Glen Cove, NY

Photo of Alana Lucidi
Signature Premier Properties
“Brandy was fantastic every step of the way and stayed consistent throughout this entire process. Highly recommended for anyone in need of a realtor.”

Harris Goldberg · West Haverstraw, NY

Photo of Brandy Seltzer
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. ”

Shreen B. · Bronx, NY

Photo of Martha & Niall Gaffney
Old Towne Living NY Inc.
“My realtor was incredible and very helpful throughout the process of selling my home.”

Edward I. · Levittown, NY

Photo of Ken Olson
HomeSmart Premier Living Realty
“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.”

Dennis T. · Glen Cove, NY

Photo of Team Carillo
Coldwell Banker
“Virginia worked well with me to sell my home. Communication was easy and she was always on time”

Jill W. · Poughkeepsie, NY

Photo of Virginia Hayes
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!”

Arnold Dennison · Chester, NY

Photo of Harmoni VanEtten
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.”

Sharon J · Middletown, NY

Photo of Imelda Otto Isles
EXP realty
“Happy to find an agent who was familiar with multi-family across the nation for my purchase.”

Marcus S. · Rochester, NY

Photo of Team Hilbert
Keller Williams Realty Greater Rochester

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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