About 380 Whippoorwill Road
This charming cottage has been completely gut renovated, offering the perfect blend of modern comfort and timeless character. Thoughtfully redesigned from top to bottom, this home is the ideal retreat—whether you're looking for a weekend getaway or a full-time residence. Located just minutes from the heart of downtown Chappaqua and mere seconds from Chappaqua Crossing and Horace Greeley High School, and Whippoorwill Park, the location couldn't be more convenient. Inside, you'll find a bright, open layout with high-end finishes throughout. Every detail has been carefully considered, new kitchen with custom cabinetry (2018) and sleek appliances to the spa-like bathrooms and cozy, sun-filled living spaces. The renovation preserved the home’s original charm while bringing in all the modern upgrades today’s buyers expect, including new systems, windows, and beautiful hardwood floors. Outside, the property offers peaceful surroundings and just the right amount of space to relax or entertain, all while being close to everything Chappaqua has to offer—shopping, dining, schools, and easy train access to NYC. This move-in-ready cottage is a rare find in one of Westchester’s most desirable communities.
Features of 380 Whippoorwill Road
| MLS® # | 815951 |
|---|---|
| Price | $625,000 |
| 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 | Active |
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 | April 10th, 2025 |
|---|---|
| Days on Market | 38 |
| Short Sale | No |
| RE / Bank Owned | No |
| Levels | One |
Listing Details
| Office | Compass Greater NY, LLC |
|---|