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.
Sold for $525,000
$525,000
380 Whippoorwill Road, Chappaqua, NY 10514
3beds
880sqft
Single Family Residence, Residential
Built in 1927
2.29 Acres Lot
$770,900 Zestimate®
$597/sqft
$5,446 Estimated rent
Home value
$770,900
$702,000 - $856,000
$5,446/mo
Zestimate® history
Owner options
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$5,446/mo
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$3,436/mo
Est. payment
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$3,436/mo
Est. payment
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Zillow last checked:
Listing updated:
Listed by:
Sari J. Shaw 917-597-7394,
Compass Greater NY, LLC 914-238-0676,
Christine Parke Anderson 214-929-6537,
Compass Greater NY, LLC
Bought with:
Fred Palma, 30PA1093036
ERA Insite Realty Services
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 881879
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Hot Water, Oil
Cooling
- Wall/Window Unit(s)
Appliances
- Included: Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater
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
- Windows: Blinds, Screens
- Basement: Crawl Space
- Attic: None
- Has fireplace: No
Interior area
- Total structure area: 880
- Total interior livable area: 880 sqft
Property
Parking
- Total spaces: 1
- Parking features: Attached, Driveway
- Garage spaces: 1
- Has uncovered spaces: Yes
Features
- Levels: One
Lot
- Size: 2.29 Acres
- Features: Level, Near Public Transit, Near School, Near Shops, Views, Wooded
Details
- Parcel number: 3600093018000020000003
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cottage
- Property subtype: Single Family Residence, Residential
Materials
- Clapboard
Condition
- Actual
- Year built: 1927
- Major remodel year: 2018
Utilities & green energy
- Sewer: Septic Tank
- Utilities for property: Trash Collection Public
Community & neighborhood
Community
- Community features: Park
Location
- Region: Chappaqua
Other
Other facts
- Listing agreement: Exclusive Right To Sell
Price history
| Date | Event | Price |
|---|---|---|
| 5/27/2026 | Listing removed | $6,500$7/sqft |
Source: Zillow Rentals Report a problem | ||
| 4/2/2026 | Listed for rent | $6,500+132.1%$7/sqft |
Source: Zillow Rentals Report a problem | ||
| 10/16/2025 | Sold | $525,000-12.5%$597/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #881879 Report a problem | ||
| 8/28/2025 | Pending sale | $600,000$682/sqft |
Source: OneKey® MLS as distributed by MLS GRID #881879 Report a problem | ||
| 8/26/2025 | Listing removed | $600,000$682/sqft |
Source: OneKey® MLS as distributed by MLS GRID #881879 Report a problem | ||
| 8/8/2025 | Price change | $600,000-4%$682/sqft |
Source: OneKey® MLS as distributed by MLS GRID #881879 Report a problem | ||
| 6/28/2025 | Listed for sale | $625,000$710/sqft |
Source: OneKey® MLS as distributed by MLS GRID #881879 Report a problem | ||
| 6/2/2025 | Listing removed | $625,000$710/sqft |
Source: OneKey® MLS as distributed by MLS GRID #815951 Report a problem | ||
| 4/11/2025 | Listed for sale | $625,000+18839.4%$710/sqft |
Source: OneKey® MLS as distributed by MLS GRID #815951 Report a problem | ||
| 4/13/2021 | Listing removed | -- |
Source: Zillow Rental Manager Report a problem | ||
| 4/12/2021 | Sold | $3,300$4/sqft |
Source: Agent Provided Report a problem | ||
| 4/7/2021 | Listed for rent | $2,800-26.3%$3/sqft |
Source: Zillow Rental Manager Report a problem | ||
| 4/17/2020 | Listing removed | $3,800$4/sqft |
Source: Compass Greater NY, LLC #H6032231 Report a problem | ||
| 4/16/2020 | Sold | $3,300-99.3%$4/sqft |
Source: Agent Provided Report a problem | ||
| 4/13/2020 | Price change | $3,800-5%$4/sqft |
Source: Compass Greater NY, LLC #H6032231 Report a problem | ||
| 4/7/2020 | Listed for rent | $4,000-11.1%$5/sqft |
Source: Compass Greater NY, LLC #H6032231 Report a problem | ||
| 11/29/2019 | Listing removed | $495,000$563/sqft |
Source: Compass Greater NY, LLC #4950007 Report a problem | ||
| 10/4/2019 | Price change | $495,000-1%$563/sqft |
Source: Compass Greater NY, LLC #4950007 Report a problem | ||
| 6/29/2019 | Price change | $500,000-4.8%$568/sqft |
Source: Compass Greater NY, LLC #4950007 Report a problem | ||
| 6/18/2019 | Price change | $525,000-8.7%$597/sqft |
Source: Compass Greater NY, LLC #4950007 Report a problem | ||
| 6/7/2019 | Listed for sale | $575,000+27.8%$653/sqft |
Source: Compass Greater NY, LLC #4950007 Report a problem | ||
| 2/7/2019 | Listing removed | $4,500$5/sqft |
Source: Owner Report a problem | ||
| 1/8/2019 | Listed for rent | $4,500$5/sqft |
Source: Owner Report a problem | ||
| 10/15/2018 | Listing removed | $4,500$5/sqft |
Source: Owner Report a problem | ||
| 9/13/2018 | Listed for rent | $4,500$5/sqft |
Source: Owner Report a problem | ||
| 1/27/2017 | Sold | $450,000$511/sqft |
Source: OneKey® MLS as distributed by MLS GRID #H4611544 Report a problem | ||
| 11/28/2016 | Pending sale | $450,000$511/sqft |
Source: Coldwell Banker Residential Brokerage - Briarcliff Office #4611544 Report a problem | ||
| 3/19/2016 | Listed for sale | $450,000$511/sqft |
Source: Coldwell Banker Residential Brokerage - Briarcliff Office #4611544 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $100,000 |
| 2024 | -- | $100,000 |
| 2023 | -- | $100,000 |
| 2022 | -- | $100,000 |
| 2021 | -- | $100,000 |
| 2020 | -- | $100,000 +25.5% |
| 2019 | -- | $79,700 |
| 2018 | -- | $79,700 |
| 2017 | -- | $79,700 |
| 2016 | -- | $79,700 |
| 2015 | -- | $79,700 |
| 2014 | -- | $79,700 |
| 2013 | -- | $79,700 |
| 2012 | -- | $79,700 |
| 2011 | -- | $79,700 |
| 2010 | -- | $79,700 |
| 2009 | -- | $79,700 |
| 2008 | -- | $79,700 |
| 2007 | -- | $79,700 |
| 2006 | -- | $79,700 |
| 2005 | -- | $79,700 |
| 2004 | -- | $79,700 |
| 2003 | -- | $79,700 |
| 2002 | -- | $79,700 |
| 2001 | -- | $79,700 |
| 2000 | -- | $79,700 |
| 1999 | -- | $79,700 |
Find assessor info on the county website
Neighborhood: 10514
Nearby schools
GreatSchools rating
- 8/10Robert E Bell SchoolGrades: 5-8Distance: 1.6 mi
- 10/10Horace Greeley High SchoolGrades: 9-12Distance: 0.8 mi
- 8/10Douglas G Grafflin SchoolGrades: PK-4Distance: 1.1 mi
Schools provided by the listing agent
- Elementary: Douglas G Grafflin School
- Middle: Robert E Bell School
- High: Horace Greeley High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$770,900
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$770,900
- New York
- Westchester County
- Chappaqua
- 10514
- 380 Whippoorwill Road
Nearby cities
Nearby zip codes
Other Chappaqua Topics
