Google street view image for 414 Whippoorwill Rd, Chappaqua, NY 10514

Sold

$1,861,180

Est. refi paymentEst. refi $5,767/mo

•

3 ba

•

4,050

sq ft

414 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Serene Pond Views And Split Rail Fence Add Country Charm To This Expanded Cape With Three Levels Of Space. Bedroom/Bath Off Kitchen Ideal For Live-in. Cathedral Ceiling Family Room With Expansive Windows Overlooking Private Rear Year. Square Footage Does Not Reflect Additional 1200 Square Feet (Approx)on Lower Level. Co In Progress. Pond Shared With Neighboring Properties.

Single-familyProperty Type

1965Year Built

1.01 acresLot Size

$460Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$1,861,180

$525K since sold in August 2006$8,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.7% higher than the average sale price ($1.81M) of 6 comparable homes.

SOLD SEP 23, 2026
$1,188,000
A
4 beds2.5 baths3,953 sq ft
11 Kitchel Rd, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC
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 SEP 24, 2026
$2,020,000
C
4 beds3.5 baths3,124 sq ft
4 Old House Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD AUG 6, 2026
$1,731,000
D
4 beds3.5 baths3,138 sq ft
14 Crossways, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD JUN 29, 2026
$1,609,031
E
4 beds2.5 baths2,443 sq ft
6 Killington St, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD JUN 12, 2026
$2,375,000
F
3 beds3.5 baths3,960 sq ft
24 North Way, Chappaqua, NY 10514
Listing by Douglas Elliman Real Estate

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,752,264

Est. take-home

List your home with Redfin and save $18,612

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$5,523/mo

Redfin rental estimate

List your home for rent

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 414 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$33,736 (+0.3%)

$80,000 + $115,570

$195,570

2025

$33,622 (+2.1%)

$80,000 + $115,570

$195,570

2024

$32,933 (+2.7%)

$80,000 + $115,570

$195,570

2023

$32,081 (+2.8%)

$80,000 + $115,570

$195,570

2022

$31,219 (+1.2%)

$80,000 + $115,570

$195,570

2021

$30,863 (+1.4%)

$80,000 + $115,570

$195,570

2020

$30,444 (+1.3%)

$80,000 + $115,570

$195,570

2019

$30,062

$80,000 + $115,570

$195,570

2018

$80,000 + $115,570

$195,570

2017

$80,000 + $115,570

$195,570

2016

$80,000 + $115,570

$195,570

2014

$80,000 + $115,570

$195,570

2013

$80,000 + $115,570

$195,570

2012

$80,000 + $136,000

$216,000

2011

$80,000 + $136,000

$216,000

2010

$80,000 + $136,000

$216,000

2009

$80,000 + $136,000

$216,000

2008

$80,000 + $136,000

$216,000

Tax history for 414 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$33,736 (+0.3%)

$80,000 + $115,570

$195,570

2025

$33,622 (+2.1%)

$80,000 + $115,570

$195,570

2024

$32,933 (+2.7%)

$80,000 + $115,570

$195,570

2023

$32,081 (+2.8%)

$80,000 + $115,570

$195,570

2022

$31,219 (+1.2%)

$80,000 + $115,570

$195,570

2021

$30,863 (+1.4%)

$80,000 + $115,570

$195,570

2020

$30,444 (+1.3%)

$80,000 + $115,570

$195,570

2019

$30,062

$80,000 + $115,570

$195,570

2018

$80,000 + $115,570

$195,570

2017

$80,000 + $115,570

$195,570

2016

$80,000 + $115,570

$195,570

2014

$80,000 + $115,570

$195,570

2013

$80,000 + $115,570

$195,570

2012

$80,000 + $136,000

$216,000

2011

$80,000 + $136,000

$216,000

2010

$80,000 + $136,000

$216,000

2009

$80,000 + $136,000

$216,000

2008

$80,000 + $136,000

$216,000

*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

1.01 Acres

Year renovated

—

Sq. Ft.

4,050

Year built

1965

Style

Single Family Residential

County

Westchester County

APN

553600A09301700020090000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

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 • 0.6mi

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

$1.77M – $2.14M

Reach more buyers when you sell with Redfin. Save up to $18,612 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

$5,880,000

8 beds9.5 baths11,725 sq ft

196 Mclain St, Bedford Corners, NY 10549

Landscaped grounds • Music room • Fitness center

Listing by Julia B Fee Sothebys Int. Rlty

$2,249,000

3 beds4 baths6,115 sq ft

33 Greenbriar Dr, Chappaqua, NY 10514

Juliet balconies • Wolf gas stove • 0.93 acre lot

Listing by Houlihan Lawrence Inc.

VIDEO TOUR

$49,500,000

8 beds9 baths26,079 sq ft

Bedford Corners, NY 10549

Exceptional scale • Elegantly renovated • 2-acre zoning

Listing by William Raveis-New York LLC

$669,000

3 beds2 baths2,211 sq ft

116 Carpenter Ave, Mount Kisco, NY 10549

Short walk to train • Local shops • Dining

Listing by Houlihan Lawrence Inc.

$959,000

3 beds2 baths1,581 sq ft

10 Horseshoe Rd, Mount Kisco, NY 10549

Private acre • One-level living • Renovated kitchen

Listing by Houlihan Lawrence Inc.

NEW 30 HRS AGO

$400,000

4 beds1 bath1,220 sq ft

86 Maple Ave, Mount Kisco, NY 10549

Colonial home • Great storage space • 6,525 sq ft lot

Listing by Coldwell Banker Realty

New listings for sale in 10514

COMING SOON

$1,825,000

4 beds3.5 baths3,164 sq ft

25 Helena Dr, Chappaqua, NY 10514

Custom paneling • Hardwood floors • Fireplace

Listing by William Raveis-New York, LLC

$799,000

2 beds2.5 baths1,244 sq ft

13 Deer Run, Chappaqua, NY 10514

Renovated condo • $625 HOA • Garage

Listing by Compass Greater NY, LLC

Home values near 414 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
404 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3556 Sq. Ft.	$2,033,310
412 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5 Baths \| 4210 Sq. Ft.	$1,888,649
14 Killington St, Chappaqua, NY 3 Beds \| 3 Baths \| 4267 Sq. Ft.	$2,022,503
31 Upland Dr, Chappaqua, NY 4 Beds \| 3 Baths \| 5661 Sq. Ft.	$3,063,355
7 Jeffrey Ln, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2958 Sq. Ft.	$1,901,236
10 Stornowaye St, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3416 Sq. Ft.	$1,597,963
15 Woodland Pl, Chappaqua, NY 3 Beds \| 3 Baths \| 2151 Sq. Ft.	$1,342,490

Address	Redfin Estimate
415 Whippoorwill Rd, Chappaqua, NY 3 Beds \| 3 Baths \| 2690 Sq. Ft.	$1,509,460
418 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 3.5 Baths \| 2804 Sq. Ft.	$1,601,988
15 Killington St, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2566 Sq. Ft.	$1,416,836
23 Woodland Pl, Chappaqua, NY 4 Beds \| 2 Baths \| 4015 Sq. Ft.	$1,843,656
9 Killington St, Chappaqua, NY 3 Beds \| 3 Baths \| 2625 Sq. Ft.	$1,687,706
6 Killington St, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2443 Sq. Ft.	$1,701,479
73 Overlook Dr, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3123 Sq. Ft.	$1,945,623

Address	Redfin Estimate
411 Whippoorwill Rd, Chappaqua, NY 3 Beds \| 3 Baths \| 3575 Sq. Ft.	$1,888,068
410 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 6 Baths \| 6241 Sq. Ft.	$2,887,956
12 Jeffrey Ln, Chappaqua, NY 5 Beds \| 4.5 Baths \| 6367 Sq. Ft.	$2,275,409
15 Jeffrey Ln, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3700 Sq. Ft.	$2,127,635
17 Woodland Pl, Chappaqua, NY 3 Beds \| 2.5 Baths \| 2295 Sq. Ft.	$1,185,923
10 Killington St, Chappaqua, NY 3 Beds \| 2 Baths \| 1608 Sq. Ft.	$1,092,367
25 Upland Dr, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3659 Sq. Ft.	$2,425,843

More real estate resources

Zip Codes
Minor Civil Divisions
Neighborhoods
Cities
Popular Searches

10536 homes for sale
10562 homes for sale
10520 homes for sale
10598 homes for sale
10549 homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Wilton homes for sale
Teaneck Township homes for sale
Weston homes for sale
Mahwah Township homes for sale
New Canaan homes for sale

Houses for rent in New Castle	Agents near me	White Plains, NY homes for sale	New Castle Housing Market
Houses for sale near me	New York, NY homes for sale	Yonkers, NY homes for sale
Land for sale near me	Manhattan, NY homes for sale	Scarsdale, NY homes for sale
Open Houses near me	Rochester, NY homes for sale	New Castle Property Records
Condos for sale near me	Buffalo, NY homes for sale	NY New Listings

Hunterbrook-Huntersville homes for sale
Bedford homes for sale
Croton Heights homes for sale

Greenwich homes for sale
New York homes for sale
Stamford homes for sale