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 |
| Sold Price | $525,000 |
| Date Sold | October 16th, 2025 |
| Bedrooms | 3 |
| Bathrooms | 2.00 |
| Full Baths | 2 |
| Square Footage | 880 |
| Acres | 2.29 |
| Taxes | $16,996 |
| Year Built | 1927 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Cottage |
| Status | Closed |
Community Information
| Address | 380 Whippoorwill Road |
|---|---|
| City | Chappaqua |
| County | Westchester County |
| State | NY |
| Zip Code | 10514 |
| Adult 55+ Community | No |
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) |
| Has Basement | Yes |
| Basement | Crawl Space |
| Fireplace | No |
Exterior
| Lot Description | Level, Near Public Transit, Near School, Near Shops, Views, Wooded |
|---|---|
| Windows | Blinds, Screens |
| Exterior | 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 | 59 |
| Short Sale | No |
| RE / Bank Owned | No |
| Levels | One |
Listing Details
| Office | Compass Greater NY, LLC |
|---|