#868090, Listing office: Compass Greater NY, LLC
$625,000 List price
380 Whippoorwill Rd Chappaqua, NY 10514
3 beds
2 full
880 sqft
2.3 acres
$710 / sqft
House
Property details
About 380 Whippoorwill Rd
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.
Highlights
Home typeSingle Family Residence
HeatingHot Water, Oil
StatusActive
CoolingWall/Window Unit(s)
Size880 sqft
Lot size2.29 Acres
Year built1927
ParkingAttached, Driveway
MLS #881879
Garage1 space
Summary
- Full Bathrooms: 2
- Appliances: Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Water Heater
- Basement: No
- Interior: 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
- Total Bedroom Count: 3
- Garage Space: 1 space
- Private Pool: No
- Parking: Attached, Driveway
- Architectural Style: Cottage
- Heating: Hot Water, Oil
- Cooling: Wall/Window Unit(s)
- List Price: $625,000
- Price/SqFt: $710
- Annual Tax Amount: $12,297
- Tax Year: 2019
- Lot: Level, Near Public Transit, Views, Wooded
- Year Built: 1927
- Living Area: 880 SqFt
- Lot Size: 2.29 Acres
- MLS Number: 881879
- MLS Name: ONEKEY2
- Office Name: Compass Greater NY, LLC
- Office Phone: (914) 238-0676
Listings courtesy of OneKey MLS as distributed by MLS GRID.
All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS.
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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the OneKey™ MLS. Real Estate listings held by brokerage firms other than this broker are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers. This information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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Information Copyright 2025, OneKey™ MLS. All Rights Reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
This advertisement does not suggest that the broker has a listing in this property or properties or that any property is currently available.
Last updated on: 7/31/2025, 11:41:27 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $100,000 | $- |
| 2022 | $100,000 | $- |
| 2021 | $100,000 | $- |
| 2020 | $100,000 | $- |
| 2019 | $79,700 | $12,297 |
| 2018 | $79,700 | $12,224 |
| 2017 | $79,700 | $11,273 |
History based on county public records data.
Nearby schools
8
Douglas G Grafflin School
Public District KG-4
1.1 mi
•650 King St
8
Roaring Brook School
Public District KG-4
2.1 mi
•530 Quaker Rd
4
Mount Kisco Elementary School
Public District KG-5
2.7 mi
•47 W Hyatt Ave
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $235,615. Most Chappaqua, NY residents have annual incomes $200k+. Residents typically live in married, with kids family. Residents of this area typically have post secondary degree education.
How much money do the neighbors make?
5%
<35k
19%
35k-100k
16%
100k-200k
60%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
What types of families live nearby?
10%
Single, No Kids
5%
Single, with Kids
32%
Married, No Kids
53%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
22%
<11 yrs old
15%
12-17 yrs old
7%
18-34 yrs old
48%
35-64 yrs old
8%
65+ yrs old
What do the neighbors do for fun?
Skiing/snowboarding
PGA/LPGA
Extreme Sports
Where do the neighbors shop?
BJs Wholesale Club
Stein Mart
Academy Sports & Outdoors
Where do the neighbors go to eat?
Panera
Cracker Barrel
Bob Evans
What do the neighbors drive?
Infiniti
Lexus
Lincoln
What do the neighbors listen to?
Adult Hits
Oldies
News/Talk/Information
All data provided by Home Junction and Claritas
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Frequently asked questions
About 380 Whippoorwill Rd
The listing price of 380 Whippoorwill Rd property is $625,000.
The property 380 Whippoorwill Rd is a house located in Chappaqua, New York, 10514.
Active Listing: 380 Whippoorwill Rd is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 380 Whippoorwill Rd are: Douglas G Grafflin School (GreatSchools Rating 8/10), Roaring Brook School (GreatSchools Rating 8/10), Mount Kisco Elementary School (GreatSchools Rating 4/10), Robert E Bell School (GreatSchools Rating 8/10), Pleasantville Middle School (GreatSchools Rating 8/10), Seven Bridges Middle School (GreatSchools Rating 10/10), Horace Greeley High School (GreatSchools Rating 10/10), Pleasantville High School (GreatSchools Rating 9/10), Byram Hills High School (GreatSchools Rating 10/10).
According to the records, the last property tax for 2019 is $12,297 (source: MLS/based on county public records data).
The property at 380 Whippoorwill Rd has 3 bedrooms and 2 bathrooms.
The property 380 Whippoorwill Rd is 880 SqFt (source: MLS/tax record).
The year of construction for 380 Whippoorwill Rd is 1927.
This home is located at 380 Whippoorwill Rd in Chappaqua, NY and zip code 10514. This 880 square foot home, which was built in 1927, sits on a 2.29 acre lot. Features: 3 bedrooms, 2 bathrooms. It has been listed on Rocket Homes since June 28, 2025 and is currently priced at $625,000.
While more than 14 listings in Chappaqua, NY in June 2025 were sold above asking price, there were more than 2 listings sold at asking price, and more than 3 were sold below. Between May and June 2025, Chappaqua, NY real estate market has seen decrease in the number of listings by 15.9%. While the average time on the market in June 2025 was 32 days, the median list price was $1,545,000.
From Rocket Homes Real Estate and based on county public records data.