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!
Active
Price cut: $30K (6/26)
$619,000
416 Whippoorwill Road, Hillsdale, NY 12529
2beds
1,500sqft
Single Family Residence
Built in 2000
5.01 Acres Lot
$608,000 Zestimate®
$413/sqft
$-- HOA
What's special
Garden shedLarge gazeboDining areaHardwood floorsFunctional kitchen
- 47 days |
- 408 |
- 8 |
Zillow last checked:
Listing updated:
Listed by:
Columbia County RE Specialist 518-325-9784,
Margaret Bower Avenia 518-697-9865,
John Avenia 518-567-4404,
Columbia County RE Specialist
Source: HVCRMLS,MLS#: 20262256
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Primary bedroom
- Description: Carpet Floor
- Level: Second
Bedroom
- Description: Carpet Floor
- Level: Second
Bathroom
- Description: Half Bath, Tile Floor
- Level: First
Bathroom
- Description: Tile Floor
- Level: Second
Dining room
- Description: Hardwood Floor
- Level: First
Great room
- Description: Hardwood Floor
- Level: First
Kitchen
- Description: Hardwood Floor
- Level: First
Living room
- Description: Hardwood Floor
- Level: First
Other
- Description: Dry Basement W/D
- Level: Lower
Heating
- Baseboard, Oil
Cooling
- Window Unit(s)
Appliances
- Included: Washer/Dryer, Refrigerator, Range, Dishwasher
- Laundry: In Basement
Features
- Flooring: Carpet, Hardwood, Tile
- Doors: Sliding Doors
- Windows: Insulated Windows
- Basement: Concrete,Partial,Unfinished
- Number of fireplaces: 1
- Fireplace features: Living Room, Propane
Interior area
- Total structure area: 1,500
- Total interior livable area: 1,500 sqft
- Finished area above ground: 1,500
- Finished area below ground: 0
Property
Features
- Levels: One and One Half
- Stories: 2
- Patio & porch: Covered, Deck, Front Porch
- Exterior features: Playground, Private Entrance, Private Yard, Smart Camera(s)/Recording
- Has view: Yes
- View description: Meadow, Panoramic, Pasture, Trees/Woods
Lot
- Size: 5.01 Acres
- Features: Back Yard, Front Yard, Landscaped, Level, Many Trees, Private, Secluded, Sloped Down
Details
- Additional structures: Gazebo, Packing Shed
- Parcel number: 135.258
- Zoning: Residential
- Special conditions: Standard
- Other equipment: Dehumidifier
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Frame, Vinyl Siding
- Foundation: Concrete Perimeter, Permanent
- Roof: Asphalt,Shingle
Condition
- New construction: No
- Year built: 2000
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Septic Tank
- Water: Well
Community & HOA
Community
- Security: 24 Hour Security
HOA
- Has HOA: No
Location
- Region: Hillsdale
Financial & listing details
- Price per square foot: $413/sqft
- Tax assessed value: $297,000
- Annual tax amount: $5,456
- Date on market: 5/11/2026
- Road surface type: Asphalt
Estimated market value
$608,000
$578,000 - $638,000
$4,409/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/26/2026 | Price change | $619,000-4.6%$413/sqft |
Source:  HVCRMLS #20262256 Report a problem | ||
| 5/10/2026 | Listed for sale | $649,000+102.8%$433/sqft |
Source: My State MLS #11741859 Report a problem | ||
| 6/29/2006 | Sold | $320,000+16.4%$213/sqft |
Source: HVCRMLS #61524 Report a problem | ||
| 2/18/2004 | Sold | $275,000+816.7%$183/sqft |
Source: Public Record Report a problem | ||
| 11/6/1998 | Sold | $30,000$20/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $297,000 |
| 2024 | -- | $297,000 |
| 2023 | -- | $297,000 |
| 2022 | -- | $297,000 |
| 2021 | -- | $297,000 |
| 2020 | -- | $297,000 |
| 2019 | -- | $297,000 -1% |
| 2018 | -- | $300,000 |
| 2017 | $6,185 | $300,000 |
| 2016 | -- | $300,000 |
| 2015 | -- | $300,000 |
| 2014 | -- | $300,000 -9.3% |
| 2013 | -- | $330,840 |
| 2012 | -- | $330,840 |
| 2011 | -- | $330,840 -10% |
| 2010 | -- | $367,600 |
| 2009 | -- | $367,600 |
| 2008 | -- | $367,600 +76.7% |
| 2007 | -- | $208,000 -20.4% |
| 2006 | -- | $261,400 |
| 2005 | -- | $261,400 +21% |
| 2004 | -- | $216,000 +43% |
| 2003 | -- | $151,000 |
| 2002 | -- | $151,000 +8.6% |
| 2001 | -- | $139,000 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 12529
Getting around
0 / 100
Car-DependentNearby schools
GreatSchools rating
- 6/10Taconic Hills Elementary SchoolGrades: PK-6Distance: 4.5 mi
- 4/10Taconic Hills High SchoolGrades: 7-12Distance: 4.5 mi
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Columbia County
- Hillsdale
- 12529
- 416 Whippoorwill Road
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