# 416 Whippoorwill Road, Hillsdale, NY 12529 > **TL;DR:** 2bd/2ba single family, $575,000 ($383/sqft), built 2000, 1,500 sqft. > Fireplace, Hardwood. Est. $3,076/mo. Listed 177 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $575,000 | | Price/sqft | $383 | | Bedrooms | 2 | | Bathrooms | 2 full | | Square Feet | 1,500 | | Year Built | 2000 | | Lot Size | 217,800 sqft (5.00 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 177 | ## Why This Home Stands Out - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,908 | | Estimated Insurance | $168 | | **Total** | **$3,076** | ## Key Amenities - Fireplace - Hardwood ## Property Highlights - Built in 2000 - 5.00 acre lot - 2 stories - Fireplace ## Description ### Agent Description 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! ## Location - **Address:** 416 Whippoorwill Road, Hillsdale, NY 12529 - **County:** Columbia - **Coordinates:** 42.215653, -73.535334 - **Google Maps:** https://www.google.com/maps?q=42.215653,-73.535334 ## Virtual Tour & Media - **Video Tour:** https://www.realestatecolumbiacounty.com ## Listing Agent - **Name:** Margaret Bower Avenia - **Brokerage:** COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC - **Broker Phone:** 5186979865 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/416-Whippoorwill-Rd_Hillsdale_NY_12529_M36090-78056?f=listhub&s=NYSMLS&m=11741859&c=propsimple) ## Photos ![416 Whippoorwill Road - Photo 1](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f4141899767r.jpg) ![416 Whippoorwill Road - Photo 2](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f3263586658r.jpg) ![416 Whippoorwill Road - Photo 3](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2183409946r.jpg) ![416 Whippoorwill Road - Photo 4](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f361627425r.jpg) ![416 Whippoorwill Road - Photo 5](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2107169603r.jpg) ![416 Whippoorwill Road - Photo 6](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2764265627r.jpg) ![416 Whippoorwill Road - Photo 7](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2197180248r.jpg) ![416 Whippoorwill Road - Photo 8](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f962479118r.jpg) ![416 Whippoorwill Road - Photo 9](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f262087027r.jpg) ![416 Whippoorwill Road - Photo 10](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2544606707r.jpg) ![416 Whippoorwill Road - Photo 11](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f1577515845r.jpg) ![416 Whippoorwill Road - Photo 12](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f413972804r.jpg) ![416 Whippoorwill Road - Photo 13](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f3620271206r.jpg) ![416 Whippoorwill Road - Photo 14](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f3518583913r.jpg) ![416 Whippoorwill Road - Photo 15](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f3767045900r.jpg) ![416 Whippoorwill Road - Photo 16](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2388737751r.jpg) ![416 Whippoorwill Road - Photo 17](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f3928562663r.jpg) ![416 Whippoorwill Road - Photo 18](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f626717270r.jpg) ![416 Whippoorwill Road - Photo 19](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f1256007357r.jpg) ![416 Whippoorwill Road - Photo 20](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f842141250r.jpg) ![416 Whippoorwill Road - Photo 21](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2634245249r.jpg) ![416 Whippoorwill Road - Photo 22](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f1678428815r.jpg) ![416 Whippoorwill Road - Photo 23](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f1491701811r.jpg) ![416 Whippoorwill Road - Photo 24](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f516420617r.jpg) ![416 Whippoorwill Road - Photo 25](http://lh.rdcpix.com/af5caa54502c91e7cf7a7854f5164819l-f2611560987r.jpg) --- **MLS#:** 11741859 | **Updated:** 2026-10-28 **Source:** listhub *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.* [View on PropertySimple](https://www.propertysimple.ai/listing/416-whippoorwill-road-hillsdale-ny-12529-2070a6955fca42e589ad7564871a979c) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/416-whippoorwill-road-hillsdale-ny-12529-2070a6955fca42e589ad7564871a979c#listing", "url": "https://www.propertysimple.ai/listing/416-whippoorwill-road-hillsdale-ny-12529-2070a6955fca42e589ad7564871a979c", "name": "416 Whippoorwill Road, Hillsdale, NY 12529", "description": "416 Whippoorwill Rd, Hillsdale, NY ~ PRIVATE SETTING!! Cape Cod style home, built in 2000, meticulously maintained and is in excellent condition inside and out. 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