380 Whippoorwill Rd
Description
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...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.
Listing Agent
![Sari Shaw]()
sari.shaw@compass.comP: (917)-597-7394
Property Details for 380 Whippoorwill Road
Property Details for 380 Whippoorwill Road
| Status | Closed |
|---|---|
| MLS # | 881879 |
| Days on Market | 59 |
| Taxes | $16,996 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Single Family |
| Year Built | 1927 |
| Lot Size | 2.29 AC / 99,752 SF |
| County | Westchester County |
Location
Sold By ERA Insite Realty Services
Virtual Tour
Building Information for 380 Whippoorwill Road
Payment Calculator
$3,975 per month
30 year fixed, 6.15% Interest
$2,559
$1,416
$0
Property Information for 380 Whippoorwill Road
- Senior Community YN: No
- Year Built Effective: 2018
- Property Attached: No
- Structure Type: false
- Levels: One
- Property Condition: Actual
- State Or Province: NY
- Water Access YN: No
- School District: Chappaqua
- Elementary School District: Chappaqua
- Elementary School: Douglas G Grafflin School
- Middle Or Junior School District: Chappaqua
- Middle Or Junior School: Robert E Bell School
- High School District: Chappaqua
- High School: Horace Greeley High School
- Lease Considered: No
- Building Units Total: 1
- Parcel Number: 3600-093-018-00002-000-0003
- Additional Fees: No
- Association: No
- Amenities: 1st Floor Bedrm, Blinds, Chefs Kitchen, Cottage, First Floor Full Bath, Granite Counters, High Speed Internet, Kitchen Island, Open Kitchen, Original Details, Park, Primary Bathroom, Screens, Walk Through Kitchen, Well
- 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
- Total Rooms: 5
- Basement: Crawl Space
- Attic Description: None
- Fireplace: No
- Location Amenities: 1st Fl Master Bedroom, Chef's Kitchen, Granit Countertops, High Speed Internet, Island Kitchen, Open Kitchen, Original Details, Walk Through Kitchen, Scenic View
- Spa: No
- Window Features: Blinds,Screens
- Exclusions: none
- Living Area: 880.00
- Foundation Details: Pillar/Post/Pier
- Basement: No
- Exterior Property Features: Attached, Driveway, Blinds, Screens, Park, Level, Near Public Transit, Near School, Near Shops, Views, Wooded
- Elevation Certificate: No
- Construction Materials: Clapboard
- Pool Private: No
- Lot Features: Level, Near Public Transit, Near School, Near Shops, Views, Wooded
- Additional Parcel: No
- Site Features: Park, Level, Near Public Transit, Near School, Near Shops, Views, Wooded
- Building Area Units: Square Feet
- Parking Features: Attached, Driveway
- Parking Total: 1.00
- Garage: Yes
- Carport: No
- Cooling: Wall/Window Unit(s)
- Heating: Hot Water, Oil
- Heat Fuel Type: Hot Water, Oil
- Number Of Heating Zones: 1
- Sewer: Septic Tank
- Water Source: Well
- Utilities: Trash Collection Public
- Green Features: Blinds, Screens, Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater, Hot Water, Oil
- Down Payment Resource: Yes
Property History for 380 Whippoorwill Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Oct 16, 2025 | Sold (Public Record) Public Record #1917940065 | $525,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 10/16/2025 | Sold (Public Record) Public Record #1917940065 | $525,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 380 Whippoorwill Road
Schools near 380 Whippoorwill Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | K to 4 | |||
| Public - | 5 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | K to 4 |
Rating | School | Distance |
|---|---|---|
Douglas G Grafflin School PublicK to 4 | ||
Robert E Bell School Public5 to 8 | ||
Horace Greeley High School Public9 to 12 | ||
Roaring Brook School PublicK to 4 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 01/07/2026 03:22 AM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.
