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Listing provided courtesy of Columbia County RE Specialist- MLS# 20262256MLS Provider

416 Whippoorwill RoadHillsdale, NY 12529

Single Family · 2 Beds · 1 Full Bath · 1 Half Bath · 1,500 Sq. ft. | 5.01 Acres
$619,000 Active

416 Whippoorwill Road Overview

Time on Site:
50 days

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!

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416 Whippoorwill Road Facts & Features

  • Type Single Family
  • Sq. ft. 1,500
  • Price/Sq.ft. $413
  • Lot 5.01 Acres

Details

General

Association/HOA

  • Association: false

School Information

  • School District: Taconic Hills Central Schools

Building Information

  • New Construction: false
  • Year Built: 2000

Location/Region

  • County Or Parish: Columbia
  • MLS Area Major: Hillsdale
  • MLS Area Minor: Hillsdale
  • Township: Hillsdale

Tax Information

  • Tax Annual Amount: 5456.0
  • Tax Assessed Value: 297000

General Information

  • Parcel Number: 135.-2-58
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Special Listing Conditions: Standard
  • Zoning: Residential

Interior

Parking Information

  • Garage: false

Beds/Baths

  • Bathrooms Full: 1
  • Bathrooms Half: 1
  • Bathrooms Total: 2
  • Bedrooms Total: 2

Building Interior

  • Above Grade Finished Area: 1500.0
  • Building Area Total: 1500.0

General Information

  • Appliances: Washer/Dryer,Refrigerator,Range,Dishwasher
  • Door Features: Sliding Doors
  • Electric: 200+ Amp Service
  • Fireplace Features: Living Room,Propane
  • Fireplace: true
  • Fireplaces Total: 1
  • Flooring: Carpet,Hardwood,Tile
  • Foundation Details: Concrete Perimeter,Permanent
  • Laundry Features: In Basement
  • Levels: One and One Half
  • Other Equipment: Dehumidifier
  • Rooms Total: 9
  • Security Features: 24 Hour Security
  • Stories: 2
  • Window Features: Insulated Windows

Exterior

Lot Information

  • Lot Features: Back Yard,Front Yard,Landscaped,Level,Many Trees,Private,Secluded,Sloped Down
  • Lot Size Acres: 5.01
  • Lot Size Area: 5.01
  • Lot Size Square Feet: 218235.6
  • Lot Size Units: Acres
  • Road Surface Type: Asphalt
  • Water Source: Well

Waterfront/View

  • View: Meadow,Panoramic,Pasture,Trees/Woods

Building Exterior/Construction

  • Architectural Style: Cape Cod
  • Construction Materials: Frame,Vinyl Siding
  • Patio And Porch Features: Covered,Deck,Front Porch
  • Roof: Asphalt,Shingle

General Information

  • Exterior Features: Playground,Private Entrance,Private Yard,Smart Camera(s)/Recording
  • Other Structures: Gazebo,Packing Shed
  • Road Frontage Type: Town
  • Sewer: Septic Tank

Room Information

Room: Bathroom

  • Level: First
  • Description: Half Bath, Tile Floor

Room: Dining Room

  • Level: First
  • Description: Hardwood Floor

Room: Great Room

  • Level: First
  • Description: Hardwood Floor

Room: Kitchen

  • Level: First
  • Description: Hardwood Floor

Room: Living Room

  • Level: First
  • Description: Hardwood Floor

Room: Other Room

  • Level: Lower
  • Description: Dry Basement W/D

Room: Bathroom

  • Level: Second
  • Description: Tile Floor

Room: Bedroom

  • Level: Second
  • Description: Carpet Floor

Room: Primary Bedroom

  • Level: Second
  • Description: Carpet Floor

416 Whippoorwill Road Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

416 Whippoorwill Road Market Data

Based on the last 30 days in this zip code

$1,400,667
Average List Price
$620
Average Price per Square Foot
6
Properties Sold
137
Average Days on Market
43
Properties for Sale
Calculations provided by Reliance Network

416 Whippoorwill Road History

Date Event Value Agent
6/26/2026Source: Hudson Valley Catskill Regional MLS Price Reduction
$619,000 -4.6%
5/10/2026Source: Hudson Valley Catskill Regional MLS Added to Database
May 10, 2026