404 Whippoorwill Rd, Chappaqua, NY 10514

Off market jul 2013 for $1M

$2,033,310

Est. refi paymentEst. refi $7,465/mo

•

3,556

sq ft

404 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Classic beauty distinguishes this totally renovated home, one of the area's most elegant period residences. Pine floors, hand-hewn beams, original fireplaces and antique fixtures highlight the exceptional interiors, while a gourmet kitchen, Waterworks baths and central air have readied the home for 21st century living. A barn and magnificent mature landscape harkens back to a less hurried era. Square footage differs from town hall-reflects architect's measurement. Additional Information: ParkingFeatures:3 Car Detached,

Single-familyProperty Type

1750Year Built

1.84 acresLot Size

$572Est. Price/Sq.Ft.

3 spacesParking

Listing by Joanne Georgiou • Houlihan Lawrence Inc.

Bought with Jean Baker • Houlihan Lawrence Inc.

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H3301916

Redfin Estimate

$2,033,310

$1.0M since sold in July 2013$13K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.6% higher than the average sale price ($1.82M) of 6 comparable homes.

SOLD AUG 13, 2026
$1,830,000
A
4 beds3 baths3,672 sq ft
734 King St, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD SEP 24, 2026
$2,020,000
B
4 beds3.5 baths3,124 sq ft
4 Old House Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD AUG 12, 2026
$2,555,000
C
5 beds3.5 baths4,166 sq ft
111 Prospect Dr, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JUN 1, 2026
$1,850,000
D
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
E
4 beds2.5 baths3,953 sq ft
11 Kitchel Rd, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC
SOLD SEP 2, 2026
$1,484,000
F
4 beds3.5 baths3,585 sq ft
67 Tripp St, Mount Kisco, NY 10549
Listing by Ginnel Real Estate

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Earn from this home

Sell

$1,342,513

Est. take-home

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Refinance

Est. cash available

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Rent

$5,528/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 404 Whippoorwill Rd

Date

Event

Price

HGMLS #3301916

Mar 14, 2014

Price Changed

$1,033,000

$290/sq ft

Jul 1, 2013

Sold

$1,033,000

$290/sq ft

May 13, 2013

Contingent

—

May 13, 2013

Price Changed

$1,249,000

$351/sq ft

Jan 28, 2013

Listed

$1,249,000

$351/sq ft

OneKey® MLS as Distributed by MLS Grid #H3301916

Jul 1, 2013

Sold

$1,033,000

$290/sq ft

Jan 28, 2013

Listed

$1,249,000

$351/sq ft

Public Records

Jun 20, 1997

Sold

$790,000

$222/sq ft

Public Records

Sep 26, 1994

Sold

$715,000

$201/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$37,380 (+0.3%)

$75,000 + $142,137

$217,137

2025

$37,257 (+2.1%)

$75,000 + $142,137

$217,137

2024

$36,496 (+2.7%)

$75,000 + $142,137

$217,137

2023

$35,552 (+2.7%)

$75,000 + $142,137

$217,137

2022

$34,604 (+1.1%)

$75,000 + $142,137

$217,137

2021

$34,218 (+1.4%)

$75,000 + $142,137

$217,137

2020

$33,753 (+1.3%)

$75,000 + $142,137

$217,137

2019

$33,329

$75,000 + $142,137

$217,137

2018

$75,000 + $142,137

$217,137

2017

$75,000 + $142,137

$217,137

2016

$75,000 + $142,137

$217,137

2014

$75,000 + $142,137

$217,137

2013

$75,000 + $142,137

$217,137

2012

$75,000 + $162,875

$237,875

2011

$75,000 + $191,000

$266,000

2010

$75,000 + $191,000

$266,000

2009

$75,000 + $191,000

$266,000

2008

$75,000 + $245,000

$320,000

Tax history for 404 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$37,380 (+0.3%)

$75,000 + $142,137

$217,137

2025

$37,257 (+2.1%)

$75,000 + $142,137

$217,137

2024

$36,496 (+2.7%)

$75,000 + $142,137

$217,137

2023

$35,552 (+2.7%)

$75,000 + $142,137

$217,137

2022

$34,604 (+1.1%)

$75,000 + $142,137

$217,137

2021

$34,218 (+1.4%)

$75,000 + $142,137

$217,137

2020

$33,753 (+1.3%)

$75,000 + $142,137

$217,137

2019

$33,329

$75,000 + $142,137

$217,137

2018

$75,000 + $142,137

$217,137

2017

$75,000 + $142,137

$217,137

2016

$75,000 + $142,137

$217,137

2014

$75,000 + $142,137

$217,137

2013

$75,000 + $142,137

$217,137

2012

$75,000 + $162,875

$237,875

2011

$75,000 + $191,000

$266,000

2010

$75,000 + $191,000

$266,000

2009

$75,000 + $191,000

$266,000

2008

$75,000 + $245,000

$320,000

*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

2.68 Acres

Year renovated

—

Sq. Ft.

3,556

Year built

1750

Style

Single Family Residential

County

Westchester County

APN

553600A09301700020070000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking Information
Parking Total: 3
Parking Features: Detached

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1

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

Interior Features
Interior Features: Eat-in Kitchen,Primary Bathroom,Walk-In Closet(s)
Window Features: Skylight(s)
Levels: Two
Patio And Porch Features: Patio

Room Information
Basement YN: Yes
Attic: Full
Rooms Total: 9
Basement: Storage Space

Bathroom Information
Bathrooms Full: 3
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Wood Siding
Security Features: Security System
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Sprinklers In Front, Sprinklers In Rear
Zoning: Res

Property Information
Stories: 2
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2012
Tax Source: Municipality
Tax Annual Amount: $33,941

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: Route 117 to Whippoorwill Road. #404 on left
County Or Parish: Westchester County

Public facts

Beds: 5
Baths: 3.0
Sq. Ft.: 3,556
Stories: —
Lot Size: 2.68 acres
Style: Single Family Residential
Year Built: 1750
Year Renovated: —
County: Westchester County
APN: 553600A09301700020070000000

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 • 1.5mi

9/10

Horace Greeley High School

Public 9-12 • 0.7mi

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

5/10 Wind Factor

26% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 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

$1.93M – $2.34M

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Home values near 404 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
398 Whippoorwill Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3312 Sq. Ft.	$1,844,295
414 Whippoorwill Road, Chappaqua, NY 5 Beds \| 3 Baths \| 4050 Sq. Ft.	$1,861,180
410 Whippoorwill Road, Chappaqua, NY 5 Beds \| 6 Baths \| 6241 Sq. Ft.	$2,887,956
15 Stornowaye Street, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4330 Sq. Ft.	$1,832,060
9 Killington Street, Chappaqua, NY 3 Beds \| 3 Baths \| 2625 Sq. Ft.	$1,687,706
5 Stornowaye Street, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4305 Sq. Ft.	$1,913,775
10 Killington Street, Chappaqua, NY 3 Beds \| 2 Baths \| 1608 Sq. Ft.	$1,092,367

Address	Redfin Estimate
394 Whippoorwill Road, Chappaqua, NY 6 Beds \| 3.5 Baths \| 4612 Sq. Ft.	$3,183,603
412 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5 Baths \| 4210 Sq. Ft.	$1,888,649
14 Killington Street, Chappaqua, NY 3 Beds \| 3 Baths \| 4267 Sq. Ft.	$2,022,503
12 Jeffrey Lane, Chappaqua, NY 5 Beds \| 4.5 Baths \| 6367 Sq. Ft.	$2,275,409
21 Stornowaye Street, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3750 Sq. Ft.	$1,861,883
10 Stornowaye Street, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3416 Sq. Ft.	$1,597,963
18 Stornowaye Street, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3145 Sq. Ft.	$1,931,505

Address	Redfin Estimate
390 Whippoorwill Road, Chappaqua, NY 4 Beds \| 4 Baths \| 5188 Sq. Ft.	$3,106,567
400 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5.5 Baths \| 6600 Sq. Ft.	$3,495,618
15 Killington Street, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2566 Sq. Ft.	$1,416,836
23 Woodland Place, Chappaqua, NY 4 Beds \| 2 Baths \| 4015 Sq. Ft.	$1,843,656
25 Attitash Street, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3912 Sq. Ft.	$1,986,277
6 Killington Street, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2443 Sq. Ft.	$1,701,479
22 Stornowaye Street, Chappaqua, NY 3 Beds \| 3 Baths \| 2946 Sq. Ft.	$1,692,420

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2013. This data may not match . Learn more.

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