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    1 home
      1 home available
      380 Whippoorwill Road, Chappaqua, NY 10514
      Closed Oct 16, 2025
      380 Whippoorwill Road, Chappaqua, NY 10514
      $525,000
      3beds
      2bath
      880sqft
      2.29acres
      House for Sale
      Down payment assistanceDown Payment Help

      380 Whippoorwill Road, Chappaqua, NY 10514

      Listing by: Compass Greater NY, LLC
      1 - 1 of 1 results
      Copyright © 2025 OneKey® MLS LLC
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
      Equal opportunity
      Membio
      OneKey® MLS
      380 Whippoorwill Road, Chappaqua, NY 10514
      Closed Oct 16, 2025
      $525,000
      Down payment assistanceDown Payment Help
      3beds
      2full,half bath
      880sqft
      2.29acres

      380 Whippoorwill Road, Chappaqua, NY 10514

      City/Town:Chappaqua   Post Office: Chappaqua     

      House for Sale by Sari J. ShawCompass Greater NY, LLC.

      Data checked -. Listing last updated 70 days ago.
      1. Overview
      2. Details
      3. More 

      This charming cottage has been completely reimagined, seamlessly blending timeless character with modern luxury. Fully gut-renovated and thoughtfully redesigned from top to bottom, this inviting home offers the perfect retreat—whether you're seeking a serene weekend escape or a full-time residence. Ideally located just minutes from downtown Chappaqua and seconds from Chappaqua Crossing, Horace Greeley High School, and Whippoorwill Park, the convenience is unmatched. Inside, the sun-drenched interior features an open layout with high-end finishes throughout. The custom kitchen (2018) is outfitted with sleek appliances and tailored cabinetry, while the beautifully updated bathrooms exude style and sophistication. Cozy living spaces and gorgeous hardwood floors enhance the home’s warmth and character. Every detail has been carefully curated, including updated systems and new windows, all while preserving the home’s original charm.

      Internet Serviceability
      Details
        Property type
      Residential
        Year built
      1927
        Heating
      Hot Water, Oil
        Cooling
      Wall/Window Unit(s)
        Total rooms
      5
        Garage
      Yes (1 space)
        City/Town
      Chappaqua
        Post Office
      Chappaqua
        Parking spots
      1
      881879
      MLS ID
      Closed
      Status
      Oct 16, 2025
      Closed
        Laundry features
        Flooring
        Fireplace
      No
        Pets allowed
        Architectural Style
      Cottage
        Basement
      Crawl Space
        View
      Interior features
      First Floor Bedroom, First Floor Full Bath, Chefs Kitchen, Granite Counters, High Speed Internet, Kitchen Island, Primary Bathroom, Open Kitchen, Original Details, Walk Through Kitchen
      Exterior features
      Lot features
      Level, Near Public Transit, Near School, Near Shops, Views, Wooded
      Appliances included
      Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater
      Construction materials
      Clapboard
      Monthly taxes
      $1,416
      Yearly taxes
      $16,996
      Community Features
      Park
      School district
      Chappaqua
      Schools
      Douglas G Grafflin School, Robert E Bell School, Horace Greeley High School
      Senior community
      No
      Common Charges
      -
      Maintenance
      -
      Additional Fees
      -
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      Listing By:
      Sari J. Shaw
      Sari J. Shaw
      CA
      Christine Parke Anderson
      Sari J. Shaw
      Sari J. Shaw
      Real Estate Salesperson, Compass Greater NY, LLC
      Direct Number 
       
      CA
      Christine Parke Anderson
      Real Estate Salesperson, Compass Greater NY, LLC
      Direct Number 
       
      Location
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      380 Whippoorwill Road, Chappaqua, NY 10514, is a 3 bedroom, 2 bathroom, 880 sqft. Single Family Residence built in 1927. This property is currently available for sale and was listed on OneKey® MLS on 6-28-2025. The MLS# for this Single Family Residence is MLS# 881879.
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
      Copyright ©2025