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Homes Under $500K in Chestertown, NY

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3 beds New construction With a pool

3 listings

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Homes Under $500K in Chestertown, NY

Homes Under $500K in Chestertown, NY

3 Listings

Homes Under $500K in Chestertown, NY

3 Listings

Price Reduced40Active
$239,000
3 bd · 1 ba · 1,225 sqft
5154 US. 9, Chestertown, NY
Angela L Mead · Gallo Realty ADK, Inc
Price Reduced28Active
$320,000
5 bd · 2 ba · 2,966 sqft
20 Vetter Avenue, Chestertown, NY
Angela L Mead · Gallo Realty ADK, Inc
Price Reduced16Active
$185,000
1 bd · 2 ba · 3,222 sqft
6378 US-9, Chestertown, NY
Angela L Mead · Gallo Realty ADK, Inc

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

AdirondackChamplain Valley MLS: Listing data courtesy of the Internet Data Exchange ("IDX") Program of the Adirondack Champlain Valley Multiple Listing Service. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing information deemed reliable but not guaranteed.
Listing information ©2026 Adirondack-Champlain Valley MLS, Inc®. All Rights Reserved. Last Updated: 2026-09-11 14:54:32 UTC

By feature

New construction
With a pool

Chestertown, NY community profile

Area: 58.4 sq. mi.

Source: HJN community data

Chestertown housing market

July 2026 · This period is still settling

Homes that sold · County records, as of Jul 28, 2026

Median sale price: $225,000$73,250–$390,000 typical range
Sales: 12
Paid in cash: 75.0%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $459,900
Homes for sale: 26

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,409 sq. ft.

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Thomas O'Leary

Realty.com

Lic. #10311208632

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632