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For Sale

416 Whippoorwill Road

Hillsdale, NY 12529

$575K
2 BD · 2 BA · 1,500 sf · 5 ac · Built 2000
The residence

416 Whippoorwill Rd, Hillsdale, NY ~ 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! 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!

At a glance
Property type
Status
Active
Year built
2000
Lot size
5 acres
Living area
1,500 sf
MLS#
11741859
Beds · Baths
2 · 2
Location

Hillsdale, NY.

Hillsdale, New York, is a market our advisors follow closely — its streets, housing stock and setting each shape what a residence here is worth and how it lives day to day. We are glad to walk you through the locale in detail, and how this particular address sits within it.

Estimated Monthly Payment+
$3K/mo
Approximate · principal & interest only
Display Currency
$575K

Indicative conversion — settlement always in USD.

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Listing courtesy of COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC · NYSMLS

My State MLS / New York State MLS.Listing data is provided by My State MLS / New York State MLS 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 or leasing. Information is deemed reliable but is not guaranteed accurate and should be independently verified.

Listings updated Sep 8, 2026

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