418 Whippoorwill Rd, Chappaqua, NY 10514

Off market sep 2015 for $880K

$1,601,988

Est. refi paymentEst. refi $6,652/mo

•

2,804

sq ft

418 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Well-maintained, freshly-painted center hall colonial, including nanny/mother-in-law suite on main floor with full bath and separate entrance. Large living room (25 x 13.5 w/bay window); large family room (19 x 13)with ajoining an updated eat-in kitchen; dining room w/bay window; master suite with updated marble/granite bathroom; main floor mud room/laundry room; rear deck; sun room (not included in sq. ft. total) Additional Information: ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1963Year Built

1.34 acresLot Size

$571Est. Price/Sq.Ft.

2 car garageParking

Listing by Michele Barnette • Clickit Realty

Bought with Barbara Brown • Houlihan Lawrence Inc.

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4508349

Redfin Estimate

$1,601,988

$722K since sold in September 2015$27K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.6% lower than the average sale price ($1.70M) of 5 comparable homes.

SOLD SEP 24, 2026
$2,020,000
A
4 beds3.5 baths3,124 sq ft
4 Old House Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD AUG 7, 2026
$1,950,000
B
4 beds3 baths2,953 sq ft
105 Cross Rdg, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD AUG 6, 2026
$1,731,000
C
4 beds3.5 baths3,138 sq ft
14 Crossways, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD SEP 23, 2026
$1,188,000
D
4 beds2.5 baths3,953 sq ft
11 Kitchel Rd, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC
SOLD MAY 11, 2026
$1,600,000
E
4 beds2.5 baths2,892 sq ft
56 Cross Ridge Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC

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Sell

$977,949

Est. take-home

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Refinance

Est. cash available

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Rent

$5,283/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 418 Whippoorwill Rd

Date

Event

Price

HGMLS #4508349

Sep 10, 2015

Sold

$880,000

$314/sq ft

Mar 10, 2015

Contingent

—

Mar 5, 2015

Listed

$880,000

$314/sq ft

Well-maintained, freshly-painted center hall colonial, including nanny/mother-in-law suite on main floor with full bath and separate entrance. Large living room (25 x 13.5 w/ bay window); large family room (19 x 13)with ajoining an updated eat-in kitchen; dining room w/ bay window; master suite with updated marble/granite bathroom; main floor mud room/laundry room; rear deck; sun room (not included in sq. ft. total)

OneKey® MLS as Distributed by MLS Grid #H4508349

Sep 9, 2015

Sold

$880,000

$314/sq ft

Mar 5, 2015

Listed

$880,000

$314/sq ft

Public Records

Sep 6, 1996

Sold

$529,000

$189/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$30,023 (+0.3%)

$36,500 + $137,100

$173,600

2025

$29,920 (+2.1%)

$36,500 + $137,100

$173,600

2024

$29,304 (+2.7%)

$36,500 + $137,100

$173,600

2023

$28,545 (+2.8%)

$36,500 + $137,100

$173,600

2022

$27,771 (+1.2%)

$36,500 + $137,100

$173,600

2021

$27,446 (+1.4%)

$36,500 + $137,100

$173,600

2020

$27,073 (+1.3%)

$36,500 + $137,100

$173,600

2019

$26,735

$36,500 + $137,100

$173,600

2018

$36,500 + $137,100

$173,600

2017

$36,500 + $137,100

$173,600

2016

$36,500 + $137,100

$173,600

2014

$36,500 + $137,100

$173,600

2013

$36,500 + $137,100

$173,600

2012

$36,500 + $137,100

$173,600

2011

$36,500 + $137,100

$173,600

2010

$36,500 + $137,100

$173,600

2009

$36,500 + $137,100

$173,600

2008

$36,500 + $137,100

$173,600

Tax history for 418 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$30,023 (+0.3%)

$36,500 + $137,100

$173,600

2025

$29,920 (+2.1%)

$36,500 + $137,100

$173,600

2024

$29,304 (+2.7%)

$36,500 + $137,100

$173,600

2023

$28,545 (+2.8%)

$36,500 + $137,100

$173,600

2022

$27,771 (+1.2%)

$36,500 + $137,100

$173,600

2021

$27,446 (+1.4%)

$36,500 + $137,100

$173,600

2020

$27,073 (+1.3%)

$36,500 + $137,100

$173,600

2019

$26,735

$36,500 + $137,100

$173,600

2018

$36,500 + $137,100

$173,600

2017

$36,500 + $137,100

$173,600

2016

$36,500 + $137,100

$173,600

2014

$36,500 + $137,100

$173,600

2013

$36,500 + $137,100

$173,600

2012

$36,500 + $137,100

$173,600

2011

$36,500 + $137,100

$173,600

2010

$36,500 + $137,100

$173,600

2009

$36,500 + $137,100

$173,600

2008

$36,500 + $137,100

$173,600

*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

3.5

Stories

—

Lot width

—

Lot depth

—

Lot size

1.33 Acres

Year renovated

—

Sq. Ft.

2,804

Year built

1963

Style

Single Family Residential

County

Westchester County

APN

553600A09301300020310000000

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: Attached, Driveway, Garage Door Opener, Garage

Garage Information
Garage Spaces: 2
Has Garage

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1

Heating & Cooling
Cooling: Central Air
Heating: Hot Water, Natural Gas

Interior Features
Interior Features: Eat-in Kitchen,Primary Bathroom
Appliances: Dishwasher, Dryer, Refrigerator, Washer, Gas Water Heater
Levels: Two
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Pull Stairs
Rooms Total: 9
Basement: Finished

Bathroom Information
Bathrooms Full: 3
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Frame, Vinyl Siding, Wood Siding
Waterfront YN: No

Lot Information
Lot Features: Corner Lot, Cul-De-Sac, Level, Near Public Transit, Near School

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

Financial

Tax Information
Tax Year: 2014
Tax Source: Other
Tax Annual Amount: $23,700

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
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: Saw Mill Parkway to Reader's Digest Rd to Rte. 117 to Whippoorwill Rd. Driveway on Pin Oak Lane
County Or Parish: Westchester County

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 2,804
Stories: —
Lot Size: 1.33 acres
Style: Single Family Residential
Year Built: 1963
Year Renovated: —
County: Westchester County
APN: 553600A09301300020310000000

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 • 0.5mi

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, 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

$1.52M – $1.84M

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Home values near 418 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
415 Whippoorwill Road, Chappaqua, NY 3 Beds \| 3 Baths \| 2690 Sq. Ft.	$1,509,460
414 Whippoorwill Road, Chappaqua, NY 5 Beds \| 3 Baths \| 4050 Sq. Ft.	$1,861,180
8 Upland Drive, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3295 Sq. Ft.	$1,614,873
15 Jeffrey Lane, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3700 Sq. Ft.	$2,127,635
11 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 3510 Sq. Ft.	$1,600,486
15 Woodland Place, Chappaqua, NY 3 Beds \| 3 Baths \| 2151 Sq. Ft.	$1,342,490
8 Jeffrey Lane, Chappaqua, NY 4 Beds \| 3 Baths \| 3813 Sq. Ft.	$1,827,599

Address	Redfin Estimate
411 Whippoorwill Road, Chappaqua, NY 3 Beds \| 3 Baths \| 3575 Sq. Ft.	$1,888,068
412 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5 Baths \| 4210 Sq. Ft.	$1,888,649
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
15 Pin Oak Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2998 Sq. Ft.	$1,545,075
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

Address	Redfin Estimate
419 Whippoorwill Road, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4473 Sq. Ft.	$2,583,494
24 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 7068 Sq. Ft.	$3,202,861
10 Pin Oak Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3439 Sq. Ft.	$1,636,613
416 Bedford Road, Chappaqua, NY 3 Beds \| 3 Baths \| 2356 Sq. Ft.	$1,395,949
7 Pin Oak Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2608 Sq. Ft.	$1,390,843
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

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2015. This data may not match . Learn more.

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