3

Chestertown, NY Homes for Sale under $100,000

Section Image
  • 37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chestertown, NY 12817
    37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chestertown, NY 12817
    /2

    $60,500

    $3K PRICE INCREASE
    • Land
    • 1.73 Acres
    • $34,971 per Acre

    37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chestertown, NY 12817

    This property has beach rights to two separate beaches. HOA Fee includes maintenance of beaches and road.Blue Bay Road is a Private Road.

    John Palermo Palermo John R

    37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chestertown, NY 12817
  • 64 Carriage Knolls Rd, Chestertown, NY 12817
    64 Carriage Knolls Rd, Chestertown, NY 12817
    64 Carriage Knolls Rd, Chestertown, NY 12817
    /25

    $59,000

    $11K PRICE DROP
    • Land
    • 3.25 Acres
    • $18,154 per Acre

    64 Carriage Knolls Rd, Chestertown, NY 12817

    Cleared and leveled lot 5-minutes outside of Chestertown. Private setting set-back in the woods. (though building lot is cleared) Perfect for a full-time home or getaway cabin. Electricity and cable available at the front of property. Large pile of rocks from excavation for property delineation or retaining areas. Must walk this property to appreciate the beauty and serenity. Adjacent 11+ acre

    Walter Swartz Gallo Realty ADK Inc

    64 Carriage Knolls Rd, Chestertown, NY 12817
  • 37 Carriage Knolls Rd, Chestertown, NY 12817
    37 Carriage Knolls Rd, Chestertown, NY 12817
    37 Carriage Knolls Rd, Chestertown, NY 12817
    /25

    $39,000

    • Land
    • 2.48 Acres
    • $15,726 per Acre

    37 Carriage Knolls Rd, Chestertown, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    37 Carriage Knolls Rd, Chestertown, NY 12817
New York Warren County

Real Estate & Homes in Chestertown, NY under $100,000

Home Prices in Chestertown, NY

The median home sale price in Chestertown, NY is $310,000, up 20% year-over-year. Homes in Chestertown sell in 37 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$310,000
Median Single Family Sale Price
$310,000
Median Townhouse Sale Price
$340,000
Median 2 Bedroom Sale Price
$224,000
Median 1 Bedroom Sale Price
$192,500
Average Price Per Sq Ft
$236
Number of Homes for Sale
10
Last 12 months Home Sales
11
Months of Supply
10.90
Median List Price
$269,950
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
20%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chestertown, there are currently 3 homes for sale priced under $100,000, providing budget-friendly options for prospective buyers. Whether you're in search of houses for sale under 100k or other property types, there are opportunities to discover your ideal home within your budget in Chestertown, NY. From cozy starter homes to properties awaiting your personal touch, these affordable residences offer an entry point into the housing market or an opportunity for real estate investment without stretching your finances.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group