419 Whippoorwill Rd, Chappaqua, NY 10514

Off market aug 2016 for $1.6M

$2,583,494

Est. refi paymentEst. refi $10,446/mo

•

4,473

sq ft

419 Whippoorwill Rd, Chappaqua, NY 10514

About this home

One of Chappaqua's finest gems! This classic 1931 four bedroom colonial with lush green lawns, in ground pool and extensive stonework has been thoroughly renovated with extensive landscaping improvements. Offering the best of both worlds it has classic details throughout, vintage moldings and hardwood flooring as well as all the modern conveniences of a luxury home that appeals to today’s buyer. It is a unique home that will satisfy the most discriminating buyer—with a very open floor plan allowing an easy flow. Formal spaces include living room and dining room are wonderful for entertaining. Casual spaces include family room, office and breakfast area. Chef's kitchen features white custom cabinetry, Carrera marble countertops and Viking, Subzero and Bosch appliances. The master is a spacious sanctuary with luxury marble bath and ample closet space. Three additional bedrooms and three baths round out the second floor. Located in the exclusive Whippoorwill area, close to all. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,

Single-familyProperty Type

1931Year Built

1.26 acresLot Size

$578Est. Price/Sq.Ft.

2 spacesParking

Listing by Susan Biggar • William Raveis-New York, LLC

Bought with Sally Slater • Douglas Elliman Real Estate

Bought with Camille Branca • Douglas Elliman Real Estate

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4617821

Redfin Estimate

$2,583,494

$888K since sold in August 2016$14K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 30.8% higher than the average sale price ($1.97M) of 6 comparable homes.

SOLD OCT 23, 2026
$3,389,000
A
4 beds6.5 baths5,563 sq ft
40 Algonquin Dr, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JUN 1, 2026
$1,850,000
B
4 beds2.5 baths3,956 sq ft
21 Kitchawan Dr, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD SEP 23, 2026
$1,188,000
C
4 beds2.5 baths3,953 sq ft
11 Kitchel Rd, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC
SOLD SEP 24, 2026
$2,020,000
D
4 beds3.5 baths3,124 sq ft
4 Old House Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD SEP 10, 2026
$1,572,999
E
3 beds4 baths3,751 sq ft
100 Byram Lake Rd, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC
SOLD AUG 13, 2026
$1,830,000
F
4 beds3 baths3,672 sq ft
734 King St, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC

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Earn from this home

Sell

$1,378,117

Est. take-home

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Refinance

Est. cash available

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Rent

$6,001/mo

Redfin rental estimate

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Market trends in 10514, NY

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

108.7%

2.3% MoM

Median sale price

$1.5M

$131K MoM

Avg. days on market

20d

3 days MoM

Recently sold homes

10 MoM

New listings for sale

COMING SOON
$1,825,000
4 beds3.5 baths3,164 sq ft
25 Helena Dr, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
$799,000
2 beds2.5 baths1,244 sq ft
13 Deer Run, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
See all

Provided by Redfin

Sale history for 419 Whippoorwill Rd

Date

Event

Price

HGMLS #4617821

Aug 10, 2016

Sold

$1,695,000

$379/sq ft

Jun 8, 2016

Contingent

—

Apr 27, 2016

Listed

$1,695,000

$379/sq ft

OneKey® MLS as Distributed by MLS Grid #H4617821

Aug 10, 2016

Sold

$1,695,000

$379/sq ft

Apr 27, 2016

Listed

$1,695,000

$379/sq ft

Public Records

Nov 12, 2009

Sold

$1,200,000

$268/sq ft

HGMLS #2911949

Aug 11, 2009

Contingent

—

Public Records

Aug 30, 2005

Sold

$1,325,000

$296/sq ft

Public Records

Nov 28, 2001

Sold

$892,500

$200/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$37,099 (+0.2%)

$70,000 + $151,040

$221,040

2025

$37,017 (+1.9%)

$70,000 + $151,040

$221,040

2024

$36,326 (+2.4%)

$70,000 + $151,040

$221,040

2023

$35,467 (+2.3%)

$70,000 + $151,040

$221,040

2022

$34,667 (+1.0%)

$70,000 + $151,040

$221,040

2021

$34,308 (+1.6%)

$70,000 + $151,040

$221,040

2020

$33,775 (+1.4%)

$70,000 + $151,040

$221,040

2019

$33,325

$70,000 + $151,040

$221,040

2018

$70,000 + $151,040

$221,040

2017

$70,000 + $151,040

$221,040

2016

$70,000 + $151,040

$221,040

2014

$70,000 + $151,040

$221,040

2013

$70,000 + $151,040

$221,040

2012

$70,000 + $151,040

$221,040

2011

$70,000 + $151,040

$221,040

2010

$70,000 + $151,040

$221,040

2009

$70,000 + $200,000

$270,000

2008

$70,000 + $200,000

$270,000

Tax history for 419 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$37,099 (+0.2%)

$70,000 + $151,040

$221,040

2025

$37,017 (+1.9%)

$70,000 + $151,040

$221,040

2024

$36,326 (+2.4%)

$70,000 + $151,040

$221,040

2023

$35,467 (+2.3%)

$70,000 + $151,040

$221,040

2022

$34,667 (+1.0%)

$70,000 + $151,040

$221,040

2021

$34,308 (+1.6%)

$70,000 + $151,040

$221,040

2020

$33,775 (+1.4%)

$70,000 + $151,040

$221,040

2019

$33,325

$70,000 + $151,040

$221,040

2018

$70,000 + $151,040

$221,040

2017

$70,000 + $151,040

$221,040

2016

$70,000 + $151,040

$221,040

2014

$70,000 + $151,040

$221,040

2013

$70,000 + $151,040

$221,040

2012

$70,000 + $151,040

$221,040

2011

$70,000 + $151,040

$221,040

2010

$70,000 + $151,040

$221,040

2009

$70,000 + $200,000

$270,000

2008

$70,000 + $200,000

$270,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

1.26 Acres

Year renovated

—

Sq. Ft.

4,473

Year built

1931

Style

Single Family Residential

County

Westchester County

APN

553600A09301700010080000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking Information
Parking Total: 2
Parking Features: Detached

Interior

Virtual Tour Information

Fireplace Information
Has Fireplace
Fireplaces Total: 2

Heating & Cooling
Cooling: Central Air
Heating: Hydro Air, Oil, Radiant

Interior Features
Interior Features: Built-in Features,Cathedral Ceiling(s),Central Vacuum,Eat-in Kitchen,Entrance Foyer,Formal Dining,Marble Counters,Primary Bathroom,Pantry,Walk-In Closet(s)
Appliances: Dishwasher, Dryer, Refrigerator, Washer, Oil Water Heater
Flooring: Hardwood
Levels: Two
Patio And Porch Features: Patio

Room Information
Basement YN: Yes
Attic: Pull Stairs
Rooms Total: 11
Basement: Full, Unfinished

Bathroom Information
Bathrooms Full: 4
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Clapboard, Frame, Wood Siding
Fencing: Fenced
Security Features: Security System
Waterfront YN: No

Pool Information
Pool Features: In Ground

Lot Information
Lot Features: Level, Near School, Near Shops

Property Information
Stories: 2
Living Area Source: Public Records
Property Sub Type: Single Family Residence
Property Condition: Actual

Financial

Tax Information
Tax Year: 2016
Tax Source: Municipality
Tax Annual Amount: $32,339

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Electric Company: Con-Edison
Sewer: Septic Tank
Utilities: Trash Collection Public

Location

School Information
Elementary School: Douglas G Grafflin School
Middle Or Junior School: Robert E Bell School
High School: Horace Greeley High School
High School District: Chappaqua

Location Information
Hamlet: Chappaqua
Directions: Bedford Road to Whippoorwill Road, first house on right.
County Or Parish: Westchester County

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 4,473
Stories: —
Lot Size: 1.26 acres
Style: Single Family Residential
Year Built: 1931
Year Renovated: —
County: Westchester County
APN: 553600A09301700010080000000

Home facts updated by county records on Sep 25, 2026

Around this home

Schools

K - 12
Preschool & daycare

Some nearby schools may not be within this home's attendance zone. Please check the Chappaqua Central School District website to verify.

Douglas G Grafflin School

Public PreK-4 • 1.2mi

10/10

Robert E Bell School

Public 5-8 • 1.4mi

9/10

Horace Greeley High School

Public 9-12 • 0.4mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 5 days in 30 years

Provided by First Street

Historical weather

Chappaqua, NY • 10514

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 4.2 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.46M – $2.97M

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New listings for sale in 10514

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Home values near 419 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
415 Whippoorwill Road, Chappaqua, NY 3 Beds \| 3 Baths \| 2690 Sq. Ft.	$1,509,460
24 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 7068 Sq. Ft.	$3,202,861
31 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 5661 Sq. Ft.	$3,063,355
416 Bedford Road, Chappaqua, NY 3 Beds \| 3 Baths \| 2356 Sq. Ft.	$1,395,949
15 Pin Oak Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2998 Sq. Ft.	$1,545,075
25 Upland Drive, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3659 Sq. Ft.	$2,425,843
2 Jeffrey Lane, Chappaqua, NY 4 Beds \| 3 Baths \| 2938 Sq. Ft.	$1,514,905

Address	Redfin Estimate
411 Whippoorwill Road, Chappaqua, NY 3 Beds \| 3 Baths \| 3575 Sq. Ft.	$1,888,068
8 Upland Drive, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3295 Sq. Ft.	$1,614,873
10 Pin Oak Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3439 Sq. Ft.	$1,636,613
11 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 3510 Sq. Ft.	$1,600,486
7 Pin Oak Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2608 Sq. Ft.	$1,390,843
403 Bedford Road, Chappaqua, NY 4 Beds \| 3 Baths \| 2141 Sq. Ft.	$1,342,764
17 Upland Drive, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3084 Sq. Ft.	$1,746,310

Address	Redfin Estimate
418 Whippoorwill Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 2804 Sq. Ft.	$1,601,988
11 Pin Oak Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3225 Sq. Ft.	$1,763,505
7 Jeffrey Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2958 Sq. Ft.	$1,901,236
405 Bedford Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2965 Sq. Ft.	$1,321,051
16 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 3584 Sq. Ft.	$2,120,518
4 Jeffrey Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2141 Sq. Ft.	$1,553,814
15 Upland Drive, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2949 Sq. Ft.	$1,831,079

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2016. This data may not match . Learn more.

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