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    • Price cut: $44K (9/8)
    $575,000

    416 Whippoorwill Road, Hillsdale, NY 12529

    2beds
    1,500sqft
    Single Family Residence
    Built in 2000
    5.01 Acres Lot
    $570,200 Zestimate®
    $383/sqft
    $-- HOA

    What's special

    Garden shedLarge gazeboDining areaHardwood floorsFunctional kitchen
    PRIVATE SETTING!! Cape Cod style home, built in 2000, meticulously maintained and is in excellent condition inside and out. The main level features a functional kitchen, dining area, bathroom, and living room centered around a propane fireplace; all with hardwood floors. A 12x12 great room with hardwood floors was added to provide additional living space. Ideally located on one of Hillsdale's prettiest country roads and in close proximity to everything that makes Hillsdale such a popular destination. Whippoorwill Road is within a short drive of Catamount Ski Area, Vine Gate Lavender Farm, the HV Rail Trail, Taghkanic State Park, The Copake-Hillsdale Farmers Market, Copake Lake, downtown Hudson and the Berkshires. The 5-acre parcel is completely tree lined for total privacy and seclusion. A garden shed, large gazebo and spacious deck overlooking the back yard make enjoying the outdoors a breeze all summer long. ''Neat as a pin'', ''cute as a button'', ''big things come in small packages''. These superlatives all ring true. You have the power to make them more than a superlative. You can make them become a reality!
    20 days
    662
    17

    Zillow last checked:

    Listing updated:

    Listed by:

    Columbia County RE Specialist 518-325-9784,

    Margaret Bower Avenia 518-697-9865

    Source: HVCRMLS,MLS#: 20265193MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 1
      • 1/2 bathrooms: 1
      Primary bedroom
      • Description: Carpet Floor
      • Level: Second
      Bedroom
      • Description: Carpet Floor
      • Level: Second
      Bathroom
      • Description: Half Bath, Tile Floor
      • Level: First
      Bathroom
      • Description: Tile Floor
      • Level: Second
      Dining room
      • Description: Hardwood Floor
      • Level: First
      Great room
      • Description: Hardwood Floor
      • Level: First
      Kitchen
      • Description: Hardwood Floor
      • Level: First
      Living room
      • Description: Hardwood Floor
      • Level: First
      Other
      • Description: Dry Basement W/D
      • Level: Lower
      Heating
      • Baseboard, Oil
      Cooling
      • Window Unit(s)
      Appliances
      • Included: Washer/Dryer, Refrigerator, Range, Dishwasher
      • Laundry: In Basement
      Features
      • Flooring: Carpet, Hardwood, Tile
      • Doors: Sliding Doors
      • Windows: Insulated Windows
      • Basement: Concrete,Partial,Unfinished
      • Number of fireplaces: 1
      • Fireplace features: Living Room, Propane
      Interior area
      • Total structure area: 1,500
      • Total interior livable area: 1,500 sqft
      • Finished area above ground: 1,500
      • Finished area below ground: 0

      Property

      Features
      • Levels: One and One Half
      • Stories: 2
      • Patio & porch: Covered, Deck, Front Porch
      • Exterior features: Playground, Private Entrance, Private Yard, Smart Camera(s)/Recording
      • Has view: Yes
      • View description: Meadow, Panoramic, Pasture, Trees/Woods
      Lot
      • Size: 5.01 Acres
      • Features: Back Yard, Front Yard, Landscaped, Level, Many Trees, Private, Secluded, Sloped Down
      Details
      • Additional structures: Gazebo, Packing Shed
      • Parcel number: 135.258
      • Zoning: Residential
      • Special conditions: Standard
      • Other equipment: Dehumidifier

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod
      • Property subtype: Single Family Residence
      Materials
      • Frame, Vinyl Siding
      • Foundation: Concrete Perimeter, Permanent
      • Roof: Asphalt,Shingle
      Condition
      • New construction: No
      • Year built: 2000

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Security: 24 Hour Security
      HOA
      • Has HOA: No
      Location
      • Region: Hillsdale

      Financial & listing details

      • Price per square foot: $383/sqft
      • Tax assessed value: $297,000
      • Annual tax amount: $3,978
      • Date on market: 9/8/2026
      • Road surface type: Asphalt

        Estimated market value

        $570,200

        $542,000 - $599,000

        $3,960/mo

        Price history

        DateEventPrice
        9/8/2026Price change$575,000-7.1%$383/sqft
        Source: HVCRMLS #20265193 Report a problem
        6/26/2026Price change$619,000-4.6%$413/sqft
        Source: HVCRMLS #20262256 Report a problem
        5/10/2026Listed for sale$649,000+102.8%$433/sqft
        Source: My State MLS #11741859 Report a problem
        6/29/2006Sold$320,000+16.4%$213/sqft
        Source: HVCRMLS #61524 Report a problem
        2/18/2004Sold$275,000+816.7%$183/sqft
        Source: Public Record Report a problem
        11/6/1998Sold$30,000$20/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $297,000
        2024-- $297,000
        2023-- $297,000
        2022-- $297,000
        2021-- $297,000
        2020-- $297,000
        2019-- $297,000 -1%
        2018-- $300,000
        2017$6,185 $300,000
        2016-- $300,000
        2015-- $300,000
        2014-- $300,000 -9.3%
        2013-- $330,840
        2012-- $330,840
        2011-- $330,840 -10%
        2010-- $367,600
        2009-- $367,600
        2008-- $367,600 +76.7%
        2007-- $208,000 -20.4%
        2006-- $261,400
        2005-- $261,400 +21%
        2004-- $216,000 +43%
        2003-- $151,000
        2002-- $151,000 +8.6%
        2001-- $139,000
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 12529

        Getting around

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