
Land with Home for Sale in Hillsdale, New York
416 Whippoorwill Rd, Hillsdale, NY 12529
416 Whippoorwill Rd, Hillsdale, one of the prettiest country roads Columbia County has to offer!! 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!
Location
- Street address
- 416 Whippoorwill Rd
- County
- Columbia County
- Zip code
- 12529
- School district
- Taconic Hills Central School District
- Elevation
- 1,144 feet
Directions
From intersection of Route 22/23 in Hillsdale, go North on Route 22 just past Firehouse to left on Whippoorwill Road, follow Whippoorwill to #416, on right, see sign.
Property details
- Acreage
- 5 acres
- Zoning
- Residential
- MLS #
- MyStateMLS 11741859
- Posted
Parcels
- 104200-135.-2-58
Details and features
Listing
- Type
- Residential
Lot
- Features
- On Golf Course
Exterior
- Parking
- Driveway
- Pool
- Deck
- Structures
- Outbuilding
Structure
- Stories
- 2
- Sewer
- Septic Tank
- Heating
- Baseboard, Oil
- Materials
- Vinyl Siding
- Roof
- Asphalt
Interior
- Room Count
- 8
- Rooms
- Bathroom x 2, Bedroom x 2, Laundry Room
- Flooring
- Hardwood
- Fireplaces
- Yes
- Features
- Entrance Foyer, Walk-In Closet(s)
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| July 2, 2026 | Price increase | $649,000 | $30,000 4.8% | MyStateMLS |
| June 27, 2026 | Price drop | $619,000 | $30,000 -4.6% | MyStateMLS |
| May 11, 2026 | New listing | $649,000 | — | MyStateMLS |
























