Skip to main contentSkip to navigation
1 / 25

Land with Home for Sale in Hillsdale, New York

416 Whippoorwill Rd, Hillsdale, NY 12529

$649,000
5 acres
Active sale
Est $3,980/mo

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!

1,500
Sq feet
2
Beds
2
Full baths
2000
Built

Location

Street address
416 Whippoorwill Rd
Zip code
12529
School district
Taconic Hills Central School District
Elevation
1,144 feet
Coordinates
42.2157, -73.5353

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

DateEventPriceChangeSource
July 2, 2026Price increase$649,000$30,000 4.8%MyStateMLS
June 27, 2026Price drop$619,000$30,000 -4.6%MyStateMLS
May 11, 2026New listing$649,000MyStateMLS
Subscribe to listing updates

Payment calculator

This 5-acre property is located at 416 Whippoorwill Rd in Hillsdale, NY 12529. The property is available for sale, priced at $649,000. It has a 1,500 square foot 2-bedroom, 2-bath house built in 2000.

Listed by Columbia County Real Estate Specialists, (518) 697-9865

Checked 1 hour agoUpdated Source

Report listing issue

Copyright © 2026 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Margaret Bower Avenia
Columbia County Real Estate Specialists
Contact listing agent Rules
By submitting, I agree to the terms of use and to be contacted by real estate professionals. Message and data rates may apply.
Contact