Google street view image for 320 Whippoorwill Rd, Chappaqua, NY 10514

Sold

$4,987,704

Est. refi paymentEst. refi $16,702/mo

•

5 ba

•

6,058

sq ft

320 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Mint Condition Historic Whippoorwill Estate With Extraordinary Views & Magnificent Rolling Lawn, Apple Orchard, Mature Rare Specimen Plantings, Pool & Poolhse/Fpl + 4 Outbuildings & Windmill Totally Renovated In 1991! Internet: Www. Holmeschappaqua. Com

Single-familyProperty Type

1830Year Built

3.42 acresLot Size

$823Est. Price/Sq.Ft.

3 spacesParking

Source:Public Records

Redfin Estimate

$4,987,704

$1.7M since sold in July 2002$177K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 107.3% higher than the average sale price ($2.41M) 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 AUG 14, 2026
$1,925,000
B
5 beds4.5 baths4,058 sq ft
765 King St, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD AUG 17, 2026
$2,032,500
C
5 beds5.5 baths6,108 sq ft
16 Carolyn Pl, Armonk, NY 10504
Listing by Houlihan Lawrence Inc.
SOLD AUG 3, 2026
$2,530,000
D
6 beds5 baths5,811 sq ft
17 Wampus Lake Dr, Armonk, NY 10504
Listing by Compass Greater NY, LLC
SOLD DEC 5, 2025
$2,060,000
E
5 beds4.5 baths4,172 sq ft
77 Haights Cross Rd, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD JUL 14, 2026
$2,500,000
F
4 beds4.5 baths5,012 sq ft
15 Haights Cross Rd, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty

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

Earn from this home

Sell

$4,699,325

Est. take-home

List your home with Redfin and save $49,877

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$6,498/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 320 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$97,866 (+0.2%)

$200,000 + $389,930

$589,930

2025

$97,680 (+1.8%)

$200,000 + $389,930

$589,930

2024

$95,907 (+2.4%)

$200,000 + $389,930

$589,930

2023

$93,652 (+2.2%)

$200,000 + $389,930

$589,930

2022

$91,645 (+0.9%)

$200,000 + $389,930

$589,930

2021

$90,829 (+1.6%)

$200,000 + $389,930

$589,930

2020

$89,406 (+1.4%)

$200,000 + $389,930

$589,930

2019

$88,205

$200,000 + $389,930

$589,930

2018

$200,000 + $389,930

$589,930

2017

$200,000 + $389,930

$589,930

2016

$200,000 + $389,930

$589,930

2014

$200,000 + $389,930

$589,930

2013

$200,000 + $389,930

$589,930

2012

$200,000 + $389,930

$589,930

2011

$200,000 + $498,000

$698,000

2010

$200,000 + $498,000

$698,000

2009

$200,000 + $498,000

$698,000

2008

$200,000 + $490,000

$690,000

Tax history for 320 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$97,866 (+0.2%)

$200,000 + $389,930

$589,930

2025

$97,680 (+1.8%)

$200,000 + $389,930

$589,930

2024

$95,907 (+2.4%)

$200,000 + $389,930

$589,930

2023

$93,652 (+2.2%)

$200,000 + $389,930

$589,930

2022

$91,645 (+0.9%)

$200,000 + $389,930

$589,930

2021

$90,829 (+1.6%)

$200,000 + $389,930

$589,930

2020

$89,406 (+1.4%)

$200,000 + $389,930

$589,930

2019

$88,205

$200,000 + $389,930

$589,930

2018

$200,000 + $389,930

$589,930

2017

$200,000 + $389,930

$589,930

2016

$200,000 + $389,930

$589,930

2014

$200,000 + $389,930

$589,930

2013

$200,000 + $389,930

$589,930

2012

$200,000 + $389,930

$589,930

2011

$200,000 + $498,000

$698,000

2010

$200,000 + $498,000

$698,000

2009

$200,000 + $498,000

$698,000

2008

$200,000 + $490,000

$690,000

*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

3.42 Acres

Year renovated

—

Sq. Ft.

6,058

Year built

1830

Style

Single Family Residential

County

Westchester County

APN

553600A10101400020120000000

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 • 1.0mi

10/10

Robert E Bell School

Public 5-8 • 1.7mi

9/10

Horace Greeley High School

Public 9-12 • 1.8mi

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

4/10 Heat Factor

7 days above 98° expected this year, 14 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 4.3 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.74M – $5.74M

Reach more buyers when you sell with Redfin. Save up to $49,877 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

OPEN SUN, 12PM TO 2PM

$999,500

4 beds2 baths2,346 sq ft

827 Sherman Ave, Thornwood, NY 10594

Generous layout • 9,993 sq ft lot • Built 1959

Listing by Houlihan Lawrence Inc.

$629,000

3 beds1.5 baths1,397 sq ft

118 Circular St, Thornwood, NY 10594

Stone fireplace • Open floor plan • Mature trees

Listing by Howard Hanna Rand Realty

$1,295,000

3 beds2.5 baths3,544 sq ft

115 Whippoorwill Rd, Armonk, NY 10504

Open floor plan • Large fireplace • Primary ensuite

Listing by William Raveis Real Estate

VIDEO TOUR

$2,995,000

5 beds6.5 baths7,141 sq ft

37 Sarles St, Armonk, NY 10504

2.98-acre estate • Four-car garage • Designer stonework

Listing by Serhant LLC

$1,575,000

3 beds3 baths2,360 sq ft

5 Byram Brook Pl, Armonk, NY 10504

Usable yard • Large deck • Patio

Listing by Houlihan Lawrence Inc.

$5,400,000

7 beds8.5 baths11,521 sq ft

2 Hollow Ridge Rd, Armonk, NY 10504

Informal dining area • Outdoor kitchen • 10-foot ceilings

Listing by Compass Greater NY, LLC

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 320 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
301 Whippoorwill Road, Chappaqua, NY 5 Beds \| 6.5 Baths \| 10594 Sq. Ft.	—
335 Whippoorwill Road, Chappaqua, NY 5 Beds \| 7 Baths \| 5566 Sq. Ft.	$3,930,441
321 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5.5 Baths \| 5195 Sq. Ft.	$3,149,192
340 Whippoorwill Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3184 Sq. Ft.	$2,426,380
9 Bessel Lane, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4843 Sq. Ft.	$3,443,898
82 Carolyn Place, Chappaqua, NY 4 Beds \| 5.5 Baths \| 6662 Sq. Ft.	$2,860,281
61 Carolyn Place, Chappaqua, NY 5 Beds \| 5.5 Baths \| 5907 Sq. Ft.	$3,076,850

Address	Redfin Estimate
344 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5 Baths \| 6450 Sq. Ft.	$3,701,737
351 Whippoorwill Road, Chappaqua, NY 5 Beds \| 7 Baths \| 8244 Sq. Ft.	$4,128,018
331 Whippoorwill Road, Chappaqua, NY 5 Beds \| 4.5 Baths \| 4130 Sq. Ft.	$2,071,313
350 Whippoorwill Road, Chappaqua, NY 4 Beds \| 4 Baths \| 4698 Sq. Ft.	$2,558,494
63 Carolyn Place, Chappaqua, NY 4 Beds \| 6 Baths \| 7286 Sq. Ft.	$3,109,414
2 Wildcat Road, Chappaqua, NY 5 Beds \| 4 Baths \| 5104 Sq. Ft.	$2,325,424
65 Carolyn Place, Chappaqua, NY 5 Beds \| 4 Baths \| 6713 Sq. Ft.	$2,998,816

Address	Redfin Estimate
311 Whippoorwill Road, Chappaqua, NY 4 Beds \| 5 Baths \| 5234 Sq. Ft.	$2,711,893
341 Whippoorwill Road, Chappaqua, NY 7 Beds \| 9 Baths \| 9664 Sq. Ft.	$7,712,108
345 Whippoorwill Road, Chappaqua, NY 6 Beds \| 6.5 Baths \| 5350 Sq. Ft.	$2,857,109
78 Carolyn Place, Chappaqua, NY 5 Beds \| 5.5 Baths \| 7593 Sq. Ft.	$3,330,827
59 Carolyn Place, Chappaqua, NY 5 Beds \| 6 Baths \| 7775 Sq. Ft.	$3,944,287
10 Bessel Lane, Chappaqua, NY 5 Beds \| 5 Baths \| 9299 Sq. Ft.	$3,792,750
71 Carolyn Place, Chappaqua, NY 5 Beds \| 7.5 Baths \| 8204 Sq. Ft.	$4,786,721

More real estate resources

Neighborhoods
Minor Civil Divisions
Zip Codes
Cities
Popular Searches

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

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

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