411 Whippoorwill Rd, Chappaqua, NY 10514

Off market jul 2016 for $1.1M

$1,888,068

Est. refi paymentEst. refi $8,494/mo

•

3,575

sq ft

411 Whippoorwill Rd, Chappaqua, NY 10514

About this home

An exquisite French-style Estate house in the prestigious Whippoorwill area with extensive gardens and stone patios surrounding a heated pool. This unique brick and stone home was built by craftsmen in a style and manner rarely duplicated today. The interior boasts sophisticated yet warm and welcoming spaces with high ceilings, 2 fireplaces and a heated sun room overlooking the gardens. A cook's kitchen, updated bathrooms, original architectural detailing and hardwood floors throughout make this completely private retreat a perfect escape from the hustle and bustle of daily life. A home which has been cherished and will continue to delight for years to come. ASSESSMENT REFLECTS FMV OF $1,435,877. OWNERS IN PROCESS OF GRIEVING ASSM'T. Additional Information: ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1939Year Built

2.42 acresLot Size

$528Est. Price/Sq.Ft.

2 spacesParking

Listing by Margaret Atkinson • Houlihan Lawrence Inc.

Listing by Cindy Glynn • William Raveis-New York, LLC

Bought with Gina Reback • Houlihan Lawrence Inc.

Redfin checked: a few seconds ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4620312

Redfin Estimate

$1,888,068

$708K since sold in July 2016$11K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.2% higher than the average sale price ($1.57M) 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 MAY 22, 2026
$1,290,000
B
3 beds3 baths3,421 sq ft
80 Roaring Brook Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
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 AUG 18, 2026
$1,510,000
D
3 beds2.5 baths2,010 sq ft
100 Devoe Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD JUL 22, 2026
$2,025,000
E
3 beds2.5 baths3,121 sq ft
40 Kings Ct, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JUL 13, 2026
$1,585,000
F
3 beds2.5 baths2,417 sq ft
148 Devoe Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC

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Sell

$1,043,608

Est. take-home

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Refinance

Est. cash available

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Rent

$5,563/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 411 Whippoorwill Rd

Date

Event

Price

HGMLS #4620312

Jul 30, 2016

Sold

$1,180,000

$330/sq ft

May 27, 2016

Contingent

—

May 9, 2016

Listed

$1,180,000

$330/sq ft

OneKey® MLS as Distributed by MLS Grid #H4620312

Jul 29, 2016

Sold

$1,180,000

$330/sq ft

May 9, 2016

Listed

$1,180,000

$330/sq ft

HGMLS #4424663

Nov 10, 2014

Sold

$1,200,000

$336/sq ft

Nov 10, 2014

Price Changed

$1,200,000

$336/sq ft

Sep 11, 2014

Contingent

—

Sep 11, 2014

Price Changed

$1,245,000

$348/sq ft

Jul 10, 2014

Listed

$1,245,000

$348/sq ft

Circa 1939 enchanting Whippoorwill French style brick home. Hilltop setting sited on 2.4 magical acres with lush formal gardens & stone terraces surrounding heated pool. Interior boasts sophisticated formal spaces with high ceilings, 2 fireplaces, cook's kitchen, grand living room & dining room making this special home perfect for gracious entertaining. Original custom architectural detailing & hardwood floors throughout . Koi pond, specimen trees, and mature plantings make this a private luxury retreat, yet close to all.

OneKey® MLS as Distributed by MLS Grid #H4424663

Nov 7, 2014

Sold

$1,200,000

$336/sq ft

Jul 10, 2014

Listed

$1,245,000

$348/sq ft

Public Records

Dec 2, 1993

Sold

$720,000

$201/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$39,275 (+0.2%)

$44,000 + $190,250

$234,250

2025

$39,190 (+1.9%)

$44,000 + $190,250

$234,250

2024

$38,460 (+2.4%)

$44,000 + $190,250

$234,250

2023

$37,550 (+4.1%)

$44,000 + $190,250

$234,250

2022

$36,067 (+1.0%)

$44,000 + $190,250

$234,250

2021

$35,696 (+1.6%)

$44,000 + $186,100

$230,100

2020

$35,141 (+1.4%)

$44,000 + $186,100

$230,100

2019

$34,673

$44,000 + $186,100

$230,100

2018

$44,000 + $186,100

$230,100

2017

$44,000 + $186,100

$230,100

2016

$44,000 + $236,000

$280,000

2014

$44,000 + $236,000

$280,000

2013

$44,000 + $236,000

$280,000

2012

$44,000 + $236,000

$280,000

2011

$44,000 + $236,000

$280,000

2010

$44,000 + $236,000

$280,000

2009

$44,000 + $236,000

$280,000

2008

$44,000 + $236,000

$280,000

Tax history for 411 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$39,275 (+0.2%)

$44,000 + $190,250

$234,250

2025

$39,190 (+1.9%)

$44,000 + $190,250

$234,250

2024

$38,460 (+2.4%)

$44,000 + $190,250

$234,250

2023

$37,550 (+4.1%)

$44,000 + $190,250

$234,250

2022

$36,067 (+1.0%)

$44,000 + $190,250

$234,250

2021

$35,696 (+1.6%)

$44,000 + $186,100

$230,100

2020

$35,141 (+1.4%)

$44,000 + $186,100

$230,100

2019

$34,673

$44,000 + $186,100

$230,100

2018

$44,000 + $186,100

$230,100

2017

$44,000 + $186,100

$230,100

2016

$44,000 + $236,000

$280,000

2014

$44,000 + $236,000

$280,000

2013

$44,000 + $236,000

$280,000

2012

$44,000 + $236,000

$280,000

2011

$44,000 + $236,000

$280,000

2010

$44,000 + $236,000

$280,000

2009

$44,000 + $236,000

$280,000

2008

$44,000 + $236,000

$280,000

*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

3.5

Stories

—

Lot width

—

Lot depth

—

Lot size

2.4 Acres

Year renovated

—

Sq. Ft.

3,544

Year built

1939

Style

Single Family Residential

County

Westchester County

APN

553600A09301700010120000000

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

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 2

Heating & Cooling
Cooling: Central Air
Heating: Forced Air, Natural Gas

Interior Features
Interior Features: Eat-in Kitchen,First Floor Bedroom,Walk-In Closet(s)
Window Features: Blinds
Appliances: Dishwasher, Dryer, Refrigerator, Washer, Gas Water Heater
Flooring: Hardwood
Levels: Two
Patio And Porch Features: Patio

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

Bathroom Information
Bathrooms Full: 3

Exterior

Exterior Features
Construction Materials: Brick
Fencing: Fenced
Waterfront YN: No

Pool Information
Pool Features: In Ground

Lot Information
Lot Features: Corner Lot, 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: 2016
Tax Source: Municipality
Tax Annual Amount: $41,056

Financial Information
Buyer Financing: Conventional

Utilities

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

Location

HOA Information
Association Amenities: Park

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 to #411 on the right.
County Or Parish: Westchester County

Community Information
Community Features: Park

Public facts

Beds: 3
Baths: 3.5
Sq. Ft.: 3,544
Stories: —
Lot Size: 2.4 acres
Style: Single Family Residential
Year Built: 1939
Year Renovated: —
County: Westchester County
APN: 553600A09301700010120000000

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 • 1.1mi

10/10

Robert E Bell School

Public 5-8 • 1.4mi

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

$1.79M – $2.17M

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Home values near 411 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
415 Whippoorwill Road, Chappaqua, NY 3 Beds \| 3 Baths \| 2690 Sq. Ft.	$1,509,460
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
31 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 5661 Sq. Ft.	$3,063,355
17 Woodland Place, Chappaqua, NY 3 Beds \| 2.5 Baths \| 2295 Sq. Ft.	$1,185,923
15 Woodland Place, Chappaqua, NY 3 Beds \| 3 Baths \| 2151 Sq. Ft.	$1,342,490
25 Upland Drive, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3659 Sq. Ft.	$2,425,843

Address	Redfin Estimate
419 Whippoorwill Road, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4473 Sq. Ft.	$2,583,494
418 Whippoorwill Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 2804 Sq. Ft.	$1,601,988
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
11 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 3510 Sq. Ft.	$1,600,486
16 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 3584 Sq. Ft.	$2,120,518
21 Woodland Place, Chappaqua, NY 3 Beds \| 3.5 Baths \| 2648 Sq. Ft.	$1,630,033

Address	Redfin Estimate
414 Whippoorwill Road, Chappaqua, NY 5 Beds \| 3 Baths \| 4050 Sq. Ft.	$1,861,180
24 Upland Drive, Chappaqua, NY 4 Beds \| 3 Baths \| 7068 Sq. Ft.	$3,202,861
8 Upland Drive, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3295 Sq. Ft.	$1,614,873
7 Jeffrey Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2958 Sq. Ft.	$1,901,236
10 Killington Street, Chappaqua, NY 3 Beds \| 2 Baths \| 1608 Sq. Ft.	$1,092,367
73 Overlook Drive, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3123 Sq. Ft.	$1,945,623
8 Jeffrey Lane, Chappaqua, NY 4 Beds \| 3 Baths \| 3813 Sq. Ft.	$1,827,599

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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