$420,000
6
3Bds
2Ba
1,488sqft
Single family home for sale
Hunt Era
Homes for Sale Under 450K in Chestertown, NY
46 Homes for Sale
Sort by:Newest Listings
3D Tour
$399,900
5
6Bds
3Ba
2,916sqft
Single family home for sale
Kw Platform
$395,000
4
5Bds
2Ba
1,286sqft
Single family home for sale
Gallo Realty Adk Inc
3D Tour
$379,900
8
3Bds
3Ba
1,660sqft
Sale Pending
Coldwell Banker Prime Properties
$375,000
7
--Bds
--Ba
7.53acres lot
Land for sale
Coldwell Banker Prime Properties
No HOA
$355,000
6
2Bds
2Ba
1,086sqft
Single family home for sale
Hunt Real Estate Era
Price Drop: $15.6K
$329,900
7
3Bds
2Ba
1,960sqft
Single family home for sale
Sherwood Group, Llc
3D Tour
New Construction
3D Tour
$239,000
8
3Bds
1Ba
1,225sqft
Single family home for sale
Gallo Realty Adk Inc
3D Tour
4a High Pines Ter, Chestertown, NY 12817
Howard Hanna Capital Inc
Building 1 Unit Available
Unit #
3D Tour
1 E High Pines Ter #E, Chestertown, NY 12817
Four Seasons Sothebys International Realty
Building 1 Unit Available
Unit #E
$200,000
7
1Bd
1Ba
704sqft
Single family home for sale
Hunt Real Estate Era
11 S Overlook Ln #UNIT B, Chestertown, NY 12817
Hunt Real Estate Era
Building 1 Unit Available
Unit #UNIT B
6378 Us 9, Chestertown, NY 12817
Gallo Realty Adk Inc
Building 1 Unit Available
Unit #
$149,900
6
--Bds
--Ba
43acres lot
Land for sale
Gallo Realty Adk Inc
4 B High Pines Ter, Chestertown, NY 12817
Roohan Realty
Building 1 Unit Available
Unit #
$88,500
7
--Bds
--Ba
12.79acres lot
Land for sale
Gallo Realty Adk Inc
$85,000
11
--Bds
--Ba
1acre lot
Land for sale
Better Way Realty Inc
$78,900
4
--Bds
--Ba
5.76acres lot
Land for sale
Gallo Realty Adk Inc
$76,900
2
--Bds
--Ba
5.1acres lot
Land for sale
Gallo Realty Adk Inc
$74,900
1
--Bds
--Ba
4.05acres lot
Land for sale
Gallo Realty Adk Inc
$74,900
4
--Bds
--Ba
4.17acres lot
Land for sale
Gallo Realty Adk Inc
$68,900
6
--Bds
--Ba
3.26acres lot
Land for sale
Gallo Realty Adk Inc
$68,900
5
--Bds
--Ba
3.11acres lot
Land for sale
Gallo Realty Adk Inc
$68,900
7
--Bds
--Ba
3.37acres lot
Land for sale
Gallo Realty Adk Inc
$68,900
5
--Bds
--Ba
3.05acres lot
Land for sale
Gallo Realty Adk Inc
$62,000
6
--Bds
--Ba
11.11acres lot
Land for sale
Gallo Realty Adk Inc
$60,500
11
--Bds
--Ba
1.73acres lot
Land for sale
John R. Palermo
$49,900
10
--Bds
--Ba
2.38acres lot
Land for sale
Gallo Realty Adk Inc
$49,500
5
--Bds
--Ba
3.36acres lot
Land for sale
Gallo Realty Adk Inc
$44,900
4
--Bds
--Ba
3.25acres lot
Land for sale
Gallo Realty Adk Inc
$39,500
6
--Bds
--Ba
2.38acres lot
Land for sale
Gallo Realty Adk Inc
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Chestertown, NY Housing Market Overview
Chestertown is moving fast, and is a seller's market. Just 1 months of supply and 39 days on the market mean less competition for buyers and more leverage for you.
Status
Seller's Market
Days on Market
39
Inventory
2
Oct 2021Jul 2024Dec 2025
Median Home Price
$462,500Up 0.38%
In Dec 2025 · YoY
Oct 2021Jul 2024Dec 2025
Mortgage Rates 30-Yr Fixed
6.23%Down 0.58%
Current rate · YoY
Loan Type
30-Year Fixed
Housing Supply
- Homes For Sale
- 2 Down 0.60%
- Newly Listed Homes
- 0 Down 0.00%
- Months of Supply
- 1 Down 4.00%
Housing Demand
- Homes Sold
- 2 Up 1.00%
- Sale-to-List Ratio
- 99% Up 3.31%
- Homes Sold Above List
- 50% Up 50.00%
30-yr fixed rate 6.23% · Data as of Dec 2025 · Source: Houzeo Research.
View Full Chestertown Market ReportNo. of Homes
Based on information from the Global Multiple Listing Service, Inc. through Oct 1, 2026, 2:45 PM. Information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. © 2026 Global Multiple Listing Service, Inc. All Rights Reserved.
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Chestertown, NY Housing Market
46
Homes Available
$ 462,500
Median List Price
39 Days
Avg on Market
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