Google satellite image for 390 Whippoorwill Rd, Chappaqua, NY 10514

Off market feb 2005 for $2.8M

$3,106,567

Est. refi paymentEst. refi $21,164/mo

•

4 ba

•

5,188

sq ft

390 Whippoorwill Rd, Chappaqua, NY 10514

About this home

390 Whippoorwill Rd is a 5,188 square foot house on a 3.06 acre lot with 4 bedrooms and 4 bathrooms. - it last sold on February 08, 2005 for $2,800,000. Based on Redfin's Chappaqua data, we estimate the home's value is $3,106,567.

Single-familyProperty Type

1985Year Built

3.06 acresLot Size

$599Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$3,106,567

$307K since sold in February 2005$66K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20% higher than the average sale price ($2.59M) of 6 comparable homes.

SOLD JUL 14, 2026
$2,500,000
A
4 beds4.5 baths5,012 sq ft
15 Haights Cross Rd, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD SEP 2, 2026
$1,484,000
B
4 beds3.5 baths3,585 sq ft
67 Tripp St, Mount Kisco, NY 10549
Listing by Ginnel Real Estate
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 DEC 26, 2025
$2,960,000
D
4 beds4.5 baths6,542 sq ft
93 Haights Cross Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD SEP 4, 2026
$3,175,000
E
4 beds5.5 baths9,284 sq ft
16 Taylor Rd, Mount Kisco, NY 10549
Listing by Houlihan Lawrence Inc.
SOLD OCT 23, 2026
$3,389,000
F
4 beds6.5 baths5,563 sq ft
40 Algonquin Dr, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC

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Earn from this home

Sell

$2,035,165

Est. take-home

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Refinance

Est. cash available

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Rent

$6,201/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 390 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$56,535 (+0.2%)

$120,000 + $219,025

$339,025

2025

$56,420 (+1.9%)

$120,000 + $219,025

$339,025

2024

$55,382 (+2.4%)

$120,000 + $219,025

$339,025

2023

$54,076 (+2.2%)

$120,000 + $219,025

$339,025

2022

$52,891 (+1.0%)

$120,000 + $219,025

$339,025

2021

$52,386 (+1.6%)

$120,000 + $219,025

$339,025

2020

$51,568 (+1.4%)

$120,000 + $219,025

$339,025

2019

$50,878

$120,000 + $219,025

$339,025

2018

$120,000 + $219,025

$339,025

2017

$120,000 + $288,000

$408,000

2016

$120,000 + $288,000

$408,000

2014

$120,000 + $288,000

$408,000

2013

$120,000 + $288,000

$408,000

2012

$120,000 + $288,000

$408,000

2011

$120,000 + $288,000

$408,000

2010

$120,000 + $288,000

$408,000

2009

$120,000 + $288,000

$408,000

2008

$120,000 + $288,000

$408,000

Tax history for 390 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$56,535 (+0.2%)

$120,000 + $219,025

$339,025

2025

$56,420 (+1.9%)

$120,000 + $219,025

$339,025

2024

$55,382 (+2.4%)

$120,000 + $219,025

$339,025

2023

$54,076 (+2.2%)

$120,000 + $219,025

$339,025

2022

$52,891 (+1.0%)

$120,000 + $219,025

$339,025

2021

$52,386 (+1.6%)

$120,000 + $219,025

$339,025

2020

$51,568 (+1.4%)

$120,000 + $219,025

$339,025

2019

$50,878

$120,000 + $219,025

$339,025

2018

$120,000 + $219,025

$339,025

2017

$120,000 + $288,000

$408,000

2016

$120,000 + $288,000

$408,000

2014

$120,000 + $288,000

$408,000

2013

$120,000 + $288,000

$408,000

2012

$120,000 + $288,000

$408,000

2011

$120,000 + $288,000

$408,000

2010

$120,000 + $288,000

$408,000

2009

$120,000 + $288,000

$408,000

2008

$120,000 + $288,000

$408,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Basement Information
Basement Type: Full

Bathroom Information
# of Full Baths: 4

Heating & Cooling
Air Conditioning Type: Central
Heating Type: Hot Air

Fireplace Information
# of Fireplaces: 2
Has Fireplace

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Mansion
Exterior Wall: Stucco

Pool Information
Pool Type: Gunite
Has Pool

Property Information
Living Sq. Ft: 5,188
Ground Floor Sq. Ft: 3,913
Building Sq. Ft: 5,688

Parking & Garage Information
# of Parking Spaces: 2
Parking Type: Attached Garage
Garage/Parking Sq. Ft: 1,236
Garage / Carport Type: Attached

Lot Information
# of Buildings: 1
Land Sq. Ft: 133,130
Legal Lot Number: 3
Legal Block Number: 1
School Tax District: CHAPPAQUA
Municipality Name: NEW CASTLE
Acres: 3.0562
Zoning Code: R-2A
State Use Description: SINGLE FAMILY RESID

Utility Information
Water Service Type: Commercial

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 5,188
Stories: —
Lot Size: 3.06 acres
Style: Single Family Residential
Year Built: 1985
Year Renovated: —
County: Westchester County
APN: 553600A09301800010030000000

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 • 1.3mi

10/10

Robert E Bell School

Public 5-8 • 1.7mi

9/10

Horace Greeley High School

Public 9-12 • 0.8mi

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

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

4/10 Wind Factor

23% 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

$2.95M – $3.57M

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Home values near 390 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
404 Whippoorwill Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3556 Sq. Ft.	$2,033,310
412 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5 Baths \| 4210 Sq. Ft.	$1,888,649
41 Jeffrey Lane, Chappaqua, NY 3 Beds \| 2.5 Baths \| 2613 Sq. Ft.	$1,400,475
12 Jeffrey Lane, Chappaqua, NY 5 Beds \| 4.5 Baths \| 6367 Sq. Ft.	$2,275,409
25 Attitash Street, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3912 Sq. Ft.	$1,986,277
49 Jeffrey Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3584 Sq. Ft.	$1,784,092
10 Killington Street, Chappaqua, NY 3 Beds \| 2 Baths \| 1608 Sq. Ft.	$1,092,367

Address	Redfin Estimate
398 Whippoorwill Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3312 Sq. Ft.	$1,844,295
400 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5.5 Baths \| 6600 Sq. Ft.	$3,495,618
15 Stornowaye Street, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4330 Sq. Ft.	$1,832,060
40 Jeffrey Lane, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3398 Sq. Ft.	$1,651,208
5 Stornowaye Street, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4305 Sq. Ft.	$1,913,775
10 Stornowaye Street, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3416 Sq. Ft.	$1,597,963
24 Attitash Street, Chappaqua, NY 4 Beds \| 2 Baths \| 5405 Sq. Ft.	$1,861,803

Address	Redfin Estimate
394 Whippoorwill Road, Chappaqua, NY 6 Beds \| 3.5 Baths \| 4612 Sq. Ft.	$3,183,603
410 Whippoorwill Road, Chappaqua, NY 5 Beds \| 6 Baths \| 6241 Sq. Ft.	$2,887,956
45 Jeffrey Lane, Chappaqua, NY 4 Beds \| 3 Baths \| 2137 Sq. Ft.	$1,406,378
19 Tall Timber, Mount Kisco, NY 4 Beds \| 3.5 Baths \| 4427 Sq. Ft.	$2,193,034
35 Ivy Hill Road, Chappaqua, NY 5 Beds \| 4.5 Baths \| 4004 Sq. Ft.	$2,792,836
6 Killington Street, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2443 Sq. Ft.	$1,701,479
20 Attitash Street, Chappaqua, NY 5 Beds \| 4 Baths \| 3156 Sq. Ft.	$1,987,235

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