416 Whippoorwill Road, Hillsdale

$649,000

2 Beds
1½ Baths
1,500 Sqft
5.01 Acres
0 Garage

This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been 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!

Essential Information
MLS® #20262256
Price$649,000
Bedrooms2
Bathrooms1.50
Full Baths1
Half Baths1
Square Footage1,500
Acres5.01
Year Built2005
TypeResidential
Sub-TypeSingle Family Residence
StyleCape Cod
StatusActive
Community Information
Address416 Whippoorwill Road
AreaHillsdale
CityHillsdale
CountyColumbia
StateNY
Zip Code12529
View

Meadow, Panoramic, Pasture, Trees/Woods

Interior
HeatingBaseboard, Oil
CoolingWindow Unit(s)
FireplaceYes
# of Fireplaces1
FireplacesLiving Room, Propane
StoriesOne and One Half
Appliances

Washer/Dryer, Refrigerator, Range, Dishwasher

Exterior
ExteriorFrame, Vinyl Siding
RoofAsphalt, Shingle
ConstructionFrame, Vinyl Siding
FoundationConcrete Perimeter, Permanent
Exterior Features

Playground, Private Entrance, Private Yard, Smart Camera(s)/Recording

Lot Description

Back Yard, Front Yard, Landscaped, Level, Many Trees, Private, Secluded, Sloped Down

School Information
DistrictTaconic Hills Central Schools
Additional Information
ZoningResidential
Listing Details
AgentMargaret Bower Avenia
Listing Courtesy of Columbia County RE Specialist
LISTING MAP

Get directions to this property:

Properties for Sale Similar to 416 Whippoorwill Road, Hillsdale, NY

Photo of Listing #20261969

81 Black Grocery Road, Hillsdale

$719,000 - 4 Beds, 3 Baths, 1,475 Sf

MLS® # 20261969

Ulster County Board of Realtors Logo
Photo of Listing #20260990

30 Ridge Lane, Hillsdale

$695,000 - 3 Beds, 3 Baths, 1,824 Sf

MLS® # 20260990

Ulster County Board of Realtors Logo
Photo of Listing #20260763

5 Adams Drive, Hillsdale

$615,000 - 3 Beds, 2 Baths, 864 Sf

MLS® # 20260763

Ulster County Board of Realtors Logo

Ulster County Board of Realtors Logo The data relating to real estate on this website comes in part from the IDX of the Multiple Listing Service of Ulster County, Inc. Real estate listings held by brokerage firms other than Flemming Realty are marked with IDX logo and the detailed information about them includes the name of the listing broker.

Copyright © 2026 by the Multiple Listing Service of Ulster County, Inc. All Rights Reserved.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

IDX information is provided exclusively 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.