380 Whippoorwill Road
Chappaqua, NY 10514
- 3 beds
- 2 baths
- 880 sqft
- ~2 acre lot
- $710 per sqft
- 1927 build
- – on site
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.
Last checked:
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Last updated Apr 11, 2025
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MLS# 815951 —
The Building
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Year Built:1927
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Basement:false
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Architectural Style:Cottage
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Construction Materials:Clapboard
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Year Built Effective:2018
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Foundation Details:Pillar/Post/Pier
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Building Area Units:Square Feet
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Window Features:Blinds, Screens
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Attic:None
Interior
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Levels:One
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Living Area:880
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Total Rooms:5
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Interior Features:Chefs Kitchen, Granite Counters, High Speed Internet, Kitchen Island, Primary Bathroom, Open Kitchen, Original Details, Walk Through Kitchen
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Fireplace:false
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Living Area Source:Public Records
Financial & Terms
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Lease Considered:false
The Property
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Lot Features:Level, Near Public Transit, Near School, Near Shops, Views, Wooded
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Lot Size Acres:2.29
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Parcel Number:3600-093-018-00002-000-0003
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Property Type:Residential
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Property Subtype:Single Family Residence
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Lot Size SqFt:99,752 Sqft
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Property Attached:false
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Property Condition:Actual
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Additional Parcels:false
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Waterfront:false
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Water Access:No
Listing Agent
- Contact info:
- Agent phone:
- (917) 597-7394
- Office phone:
- (914) 238-0676
Taxes
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Tax Year:2024
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Tax Source:Municipality
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Tax Annual Amount:16996
Beds
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Total Bedrooms:3
Baths
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Full Baths:2
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Total Baths:2
The Listing
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Special Listing Conditions:None
Heating & Cooling
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Heating:Hot Water, Oil
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Cooling:Wall/Window Unit(s)
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# of Heating Zones:1
Utilities
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Sewer:Septic Tank
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Utilities:Trash Collection Public
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Water Source:Well
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Electric Company:Con Edison
Appliances
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Appliances:Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater
Schools
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High School:Horace Greeley High School
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Elementary School:Douglas G Grafflin School
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High School District:Chappaqua
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Middle School:Robert E Bell School
The Community
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Association:false
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Senior Community:false
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Additional Fees:No
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Pool Private:false
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Spa:false
Parking
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Parking Features:Attached, Driveway
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Parking Total:1
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Garage:true
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Garage Spaces:1
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Carport:false
Monthly cost estimate
Asking price
$625,000
| Expense | Monthly cost |
|---|---|
|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$3,346
|
| Taxes | $1,416 |
| Insurance | $171 |
| Utilities | $315 See report |
| Total | $5,248/mo.* |
| *This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
| Date | Event | Source | Price | % Change |
|---|---|---|---|---|
|
4/11/25
Apr 11, 2025
|
Listed / Active | ONEKEY | $625,000 | 38.9% (4.7% / YR) |
|
1/27/17
Jan 27, 2017
|
ONEKEY | $450,000 |
