22

Chester, NY Homes for Sale under $100,000

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  • 15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    /5

    $54,900

    • Land
    • 10.14 Acres
    • $5,414 per Acre

    15 Deer Run, Chester, NY 12817

    10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

    Patricia Seitz McAlonen Pearsall Realty

    15 Deer Run, Chester, NY 12817
  • 72 Carriage Knoll Rd, Chester, NY 12817
    72 Carriage Knoll Rd, Chester, NY 12817
    72 Carriage Knoll Rd, Chester, NY 12817
    /23

    $68,900

    • Land
    • 3.11 Acres
    • $22,154 per Acre

    72 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    72 Carriage Knoll Rd, Chester, NY 12817
  • 71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    /17

    $59,900

    • Land
    • 1.89 Acres
    • $31,693 per Acre

    71 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    71 Carriage Knoll Rd, Chester, NY 12817
  • 77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    /19

    $74,900

    • Land
    • 4.17 Acres
    • $17,962 per Acre

    77 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    77 Carriage Knoll Rd, Chester, NY 12817
  • 62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    /23

    $62,000

    • Land
    • 11.11 Acres
    • $5,581 per Acre

    62 Carriage Knolls Rd, Chester, 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

    62 Carriage Knolls Rd, Chester, NY 12817
  • 20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    /7

    $49,500

    • Land
    • 3.36 Acres
    • $14,732 per Acre

    20 Carriage Knolls Rd, Chester, 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

    20 Carriage Knolls Rd, Chester, NY 12817
  • 98 Carriage Knoll Rd, Chester, NY 12817
    98 Carriage Knoll Rd, Chester, NY 12817
    98 Carriage Knoll Rd, Chester, NY 12817
    /20

    $68,900

    • Land
    • 3.26 Acres
    • $21,135 per Acre

    98 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    98 Carriage Knoll Rd, Chester, NY 12817
  • L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    /3

    $75,000

    • Land
    • 12 Acres
    • $6,250 per Acre

    L62.2 Moffitt Rd, Chester, NY 12817

    12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

    Carol Monroe Najer Realty

    L62.2 Moffitt Rd, Chester, NY 12817
  • 34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    /8

    $39,500

    • Land
    • 1.82 Acres
    • $21,703 per Acre

    34 Carriage Knolls Rd, Chester, 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

    34 Carriage Knolls Rd, Chester, NY 12817
  • 3-4 Adirondack Heights Rd, Chester, NY 12817
    3-4 Adirondack Heights Rd, Chester, NY 12817
    3-4 Adirondack Heights Rd, Chester, NY 12817
    /33

    $89,500

    • Land
    • 12.79 Acres
    • $6,998 per Acre

    3-4 Adirondack Heights Rd, Chester, NY 12817

    Seller financing now available. 12.79 acres of mixed forest and wetlands. Perc tests and engineered plot plans have been completed. APA approved building sites with well & septic locations identified. (2-lots can each be built upon or just have one large lot) Power at the road pedestal box. Tons of hemlock, spruce, and pine trees throughout. Close to Chestertown, 20-minutes to Gore Mountain or

    Walter Swartz Gallo Realty ADK Inc

    3-4 Adirondack Heights Rd, Chester, NY 12817
  • 85 Carriage Knoll Rd, Chester, NY 12817
    85 Carriage Knoll Rd, Chester, NY 12817
    85 Carriage Knoll Rd, Chester, NY 12817
    /19

    $74,900

    • Land
    • 4.05 Acres
    • $18,494 per Acre

    85 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    85 Carriage Knoll Rd, Chester, NY 12817
  • 86 Carriage Knoll Rd, Chester, NY 12817
    86 Carriage Knoll Rd, Chester, NY 12817
    86 Carriage Knoll Rd, Chester, NY 12817
    /22

    $68,900

    • Land
    • 3.37 Acres
    • $20,445 per Acre

    86 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    86 Carriage Knoll Rd, Chester, NY 12817
  • 112 Carriage Knoll Rd, Chester, NY 12817
    112 Carriage Knoll Rd, Chester, NY 12817
    112 Carriage Knoll Rd, Chester, NY 12817
    /23

    $76,900

    • Land
    • 5.1 Acres
    • $15,078 per Acre

    112 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    112 Carriage Knoll Rd, Chester, NY 12817
  • 60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    /10

    $37,500

    • Land
    • 1.62 Acres
    • $23,148 per Acre

    60 Carriage Knolls Rd, Chester, 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

    Walter Swartz Gallo Realty ADK Inc

    60 Carriage Knolls Rd, Chester, NY 12817
  • 106 Carriage Knoll Rd, Chester, NY 12817
    106 Carriage Knoll Rd, Chester, NY 12817
    106 Carriage Knoll Rd, Chester, NY 12817
    /25

    $78,900

    • Land
    • 5.76 Acres
    • $13,698 per Acre

    106 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    106 Carriage Knoll Rd, Chester, NY 12817
  • L4-5 Marina Rd, Chester, NY 12817
    L4-5 Marina Rd, Chester, NY 12817
    L4-5 Marina Rd, Chester, NY 12817
    /5

    $74,900

    • Land
    • 1.79 Acres
    • $41,844 per Acre

    L4-5 Marina Rd, Chester, NY 12817

    This is two lots combined for better access and development and has beach rights to two beaches shown on map. HOA Owner's association fee includes beach maintenance. HOA board is working toward the possibility of installing a boat docksystem for the future. Presently there is space for non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's LLC

    John Palermo John R. Palermo

    L4-5 Marina Rd, Chester, NY 12817
  • 82 Carriage Knoll Rd, Chester, NY 12817
    82 Carriage Knoll Rd, Chester, NY 12817
    82 Carriage Knoll Rd, Chester, NY 12817
    /23

    $68,900

    • Land
    • 3.05 Acres
    • $22,590 per Acre

    82 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    82 Carriage Knoll Rd, Chester, NY 12817
  • L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    /31

    $59,500

    • Land
    • 5.42 Acres
    • $10,978 per Acre

    L7 Macglashan Ln, Chester, NY 12817

    Very nice 5.42 acres of property with plenty of secluded building options. Gently sloping topography with mixed hardwood and conifers throughout. An abundance of wildlife signs from end to end of this parcel. This property is zoned ''Rural Use'' and would be used ideally for a home or cabin (one-primary single family residence) with garage or other auxiliary building. Seller financing possible

    Walter Swartz Gallo Realty ADK Inc

    L7 Macglashan Ln, Chester, NY 12817
  • 38 Granite Ridge Rd, Chester, NY 12817
    38 Granite Ridge Rd, Chester, NY 12817
    38 Granite Ridge Rd, Chester, NY 12817
    /19

    $83,500

    • Land
    • 2.84 Acres
    • $29,401 per Acre

    38 Granite Ridge Rd, Chester, NY 12817

    Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

    Nicholas Khachadourian KW Platform

    38 Granite Ridge Rd, Chester, NY 12817
  • 22 Carriage Knolls Rd, Chester, NY 12817
    22 Carriage Knolls Rd, Chester, NY 12817
    22 Carriage Knolls Rd, Chester, NY 12817
    /7

    $39,500

    • Land
    • 2.38 Acres
    • $16,597 per Acre

    22 Carriage Knolls Rd, Chester, 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

    22 Carriage Knolls Rd, Chester, NY 12817
  • 13 Carriage Knolls Rd, Chester, NY 12817
    13 Carriage Knolls Rd, Chester, NY 12817
    13 Carriage Knolls Rd, Chester, NY 12817
    /16

    $37,500

    • Land
    • 2 Acres
    • $18,750 per Acre

    13 Carriage Knolls Rd, Chester, 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

    13 Carriage Knolls Rd, Chester, NY 12817
  • 102 Carriage Knoll Rd, Chester, NY 12817
    102 Carriage Knoll Rd, Chester, NY 12817
    102 Carriage Knoll Rd, Chester, NY 12817
    /24

    $74,900

    • Land
    • 4.31 Acres
    • $17,378 per Acre

    102 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    102 Carriage Knoll Rd, Chester, NY 12817
New York Orange County Chester

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

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 58 days on the market compared to the national average of 54 days. The median sale price for homes in Chester, NY over the last 12 months is $520,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$520,000
Median Single Family Sale Price
$655,000
Median Townhouse Sale Price
$327,500
Median 2 Bedroom Sale Price
$310,000
Average Price Per Sq Ft
$268
Number of Homes for Sale
28
Last 12 months Home Sales
101
Months of Supply
3.30
Median List Price
$541,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 22 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 Chester, 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.

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