About 416 Whippoorwill Road
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!
Features of 416 Whippoorwill Road
| MLS® # | 20262256 |
|---|---|
| Price | $619,000 |
| Bedrooms | 2 |
| Bathrooms | 1.50 |
| Full Baths | 1 |
| Half Baths | 1 |
| Square Footage | 1,500 |
| Acres | 5.01 |
| Year Built | 2000 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Cape Cod |
| Status | Active |
Community Information
| Address | 416 Whippoorwill Road |
|---|---|
| Area | Hillsdale |
| City | Hillsdale |
| County | Columbia |
| State | NY |
| Zip Code | 12529 |
Amenities
| View | Meadow, Panoramic, Pasture, Trees/Woods |
|---|---|
| Is Waterfront | No |
Interior
| Appliances | Washer/Dryer, Refrigerator, Range, Dishwasher |
|---|---|
| Heating | Baseboard, Oil |
| Cooling | Window Unit(s) |
| Has Basement | Yes |
| Basement | Concrete, Partial, Unfinished |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Fireplaces | Living Room, Propane |
| Stories | One and One Half |
Exterior
| Exterior | Frame, Vinyl Siding |
|---|---|
| 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 |
| Roof | Asphalt, Shingle |
| Construction | Frame, Vinyl Siding |
| Foundation | Concrete Perimeter, Permanent |
School Information
| District | Taconic Hills Central Schools |
|---|
Additional Information
| Date Listed | May 11th, 2026 |
|---|---|
| Days on Market | 66 |
| Zoning | Residential |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Margaret Bower Avenia |
|---|---|
| Agent | John Avenia |
| Office | Columbia County RE Specialist |