380 Whippoorwill Road, Chappaqua, NY

$600,000

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3

Beds

2

Baths

880

Square feet

2.29

Acres

About 380 Whippoorwill Road

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.

Features of 380 Whippoorwill Road

MLS® # 881879
Price $600,000
Bedrooms 3
Bathrooms 2.00
Full Baths 2
Internal Footage 880
Square Footage 99752
Acres 2.29
Year Built 1927
Type Residential
Sub-Type Single Family Residence
Style Cottage
Status Pending

Community Information

Address 380 Whippoorwill Road
City Chappaqua
County Westchester County
State NY
Zip Code 10514

Amenities

Utilities Trash Collection Public
Parking Spaces 1
Parking Attached, Driveway
# of Garages 1
Is Waterfront No
Has Pool No

Interior

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
Appliances Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater
Heating Hot Water, Oil
Cooling Wall/Window Unit(s)
Fireplace No
Has Basement Yes
Basement Crawl Space

Exterior

Lot Description Level, Near Public Transit, Near School, Near Shops, Views, Wooded
Windows Blinds, Screens
Construction Clapboard

School Information

District Chappaqua
Elementary Douglas G Grafflin School
Middle Robert E Bell School
High Horace Greeley High School

Additional Information

Date Listed June 27th, 2025
Days on Market 106
Short Sale No
RE / Bank Owned No

Listing Details

Listing Provided Courtesy ofCompass Greater NY, LLC
Contact Info914-238-0676

Listing Map

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