380 Whippoorwill Road, Chappaqua, NY 10514
Local realty services provided by:Better Homes and Gardens Real Estate Green Team



380 Whippoorwill Road,Chappaqua, NY 10514
$600,000
- 3 Beds
- 2 Baths
- 880 sq. ft.
- Single family
- Active
Listed by:christine parke anderson
Office:compass greater ny, llc.
MLS#:881879
Source:One Key MLS
Price summary
- Price:$600,000
- Price per sq. ft.:$681.82
About this home
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.
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Home facts
- Year built:1927
- Listing Id #:881879
- Added:125 day(s) ago
- Updated:August 08, 2025 at 03:39 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:2
- Full bathrooms:2
- Living area:880 sq. ft.
Heating and cooling
- Heating:Hot Water, Oil
Structure and exterior
- Year built:1927
- Building area:880 sq. ft.
- Lot area:2.29 Acres
Schools
- High school:Horace Greeley High School
- Middle school:Robert E Bell School
- Elementary school:Douglas G Grafflin School
Utilities
- Water:Well
- Sewer:Septic Tank
Finances and disclosures
- Price:$600,000
- Price per sq. ft.:$681.82
- Tax amount:$16,996 (2024)
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