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For saleReduced $74,000 from $649,000Virtual tour

$575,000

2 beds1,500 sq ft5 acres

416 Whippoorwill RoadHillsdale, NY 12529

Homes, condos and townhomes · MLS 11741859 · Listed 173 days ago (May 10, 2026)

4.3 mi straight line to Catamount Mountain Resort (alpine resort) · Ski access details

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For sale: On the market and available to show.

About this property

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!

Description provided by the listing brokerage.

Ski access and nearby skiing

Why this listing is on Where2Ski: Measured distance to a ski area. It sits within 25 straight-line miles of an operating ski area's mapped entrance or base.

Nearby ski areas with straight-line distance
Ski areaTypeStraight-line distanceMeasured to
Catamount Mountain ResortNY · homes near itAlpine resort4.3 miBase parking lot (unnamed OSM lot inside Catamount Mountain Resort area)Visitor entrance, lodge or trailhead
Ski ButternutMA · homes near itAlpine resort12 miBase areaBase area (mapped point)
Bousquet MountainMA · homes near itLocal ski area19 miBase areaBase area (mapped point)
Otis Ridge Ski AreaMA · homes near itLocal ski area22 miBase areaBase area (mapped point)
Jiminy Peak Mountain ResortMA · homes near itAlpine resort26 miBase areaBase area (mapped point)
Mohawk Mountain Ski AreaCT · homes near itAlpine resort29 miBase areaBase area (mapped point)

Straight-line miles to each ski area's base or entrance, measured Oct 30, 2026, 5:16 PM UTC. Winter drives can take longer.

Ski access claims

The listing doesn't describe ski-in, ski-out, a short walk or a shuttle. The agent can tell you how owners get to the slopes.

Ski access is as described by the listing brokerage. Confirm trail access, easements and any pass or membership with Margaret Bower Avenia of COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC.

Features for skiers

  • Fireplace (mentioned in description)

How listings qualify · Report a wrong distance or ski-access claim

Facts

List price
$575,000
Original list price
$649,000
Status
For sale
Property type
House
Bedrooms
2
Full baths
2
Interior area
1,500 sq ft
Lot size
5 acres
Year built
2000
Stories
2
County
Columbia County
MLS number
11741859
Annual property tax (2026)
$545,935

Facts are provided by the listing brokerage.

Features

Interior

  • Walk-In Closet(s)
  • Entrance Foyer

Appliances

  • Washer
  • Range
  • Microwave
  • Refrigerator
  • Dryer
  • Dishwasher

Flooring

  • Hardwood

Basement

  • Unfinished

Heating

  • Baseboard
  • Oil

Parking

  • Driveway

Construction

  • Vinyl Siding

Roof

  • Asphalt

Sewer

  • Septic Tank

Lot

  • On Golf Course

Virtual tours

Open virtual tour on www.realestatecolumbiacounty.com

Location

Pin placed from the listing's coordinates, which can be approximate. See more listings in Hillsdale.

Price and status history

  • Original list price reported by the brokerage: $649,000

Changes seen in MyStateMLS data since Oct 29, 2026. Sold prices are not published.

Estimate a monthly payment

$115,000
Illustrative. Replace with a quote from your lender.
From the listing (tax year 2026). Taxes can change after a sale.
Get a quote; rates vary widely by location.
Manufactured homes on a leased lot.
Applied only while the loan is over 80% of the price. Illustrative.

Estimated monthly payment

$48,569 per month

Principal and interest$2,908
Property tax$45,495
Homeowners insurance$167
Loan amount$460,000
Total interest over the term$586,705

An estimate for comparison only. Actual rates, taxes, insurance, PMI and fees depend on your lender, credit, location and loan program.

Similar listings near Catamount Mountain Resort

The same type of property, priced $431,250 to $718,750 and a similar distance from Catamount Mountain Resort, newest first. See all matches

Questions to ask before you buy

Good questions for any home near the slopes.

  1. How is the property reached in winter, and who plows the road and driveway?A short straight-line distance can still mean a long or seasonal drive. Private roads, gates and mountain passes all shape winter access.
  2. Is there documented ski access from the property (trail, easement, lift), and does it transfer to a buyer?Rights to cross neighboring land or use a lift come from recorded easements and agreements, so a ski-in or ski-out description is where the question starts.
  3. Are there association, resort or club fees, and what do they cover?Some ski-area communities charge fees that cover only certain amenities, so ask what lift tickets, passes and services are included.
  4. Are there rules on renting the home short-term or long-term?Local ordinances, association covenants and deed restrictions all set rental rules, and they differ from place to place.
  5. What do heating, snow removal, winterization and utilities cost over a season?Ownership costs in snow country often run higher than the mortgage estimate suggests.
  6. For land: is there legal year-round access, and what utilities, septic and building rules apply?Seasonal roads and steep lots can limit what can be built and when it can be reached.

Printable due-diligence checklist · Ski home ownership budget

Guides and next steps

Listing courtesy of COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC. Listing agent: Margaret Bower Avenia. Listings provided by MyStateMLS.

Listing updated Sep 9, 2026, 1:18 AM UTC, MyStateMLS data received Oct 30, 2026, 5:01 PM UTC. Information deemed reliable but not guaranteed.