Google street view image for 5 Whippoorwill Lake Rd, Chappaqua, NY 10514

Off market sep 1990 for $569K

$1,662,036

Est. refi paymentEst. refi $4,458/mo

•

2.5 ba

•

2,863

sq ft

5 Whippoorwill Lake Rd, Chappaqua, NY 10514

About this home

5 Whippoorwill Lake Rd is a 2,863 square foot house on a 1 acre lot with 4 bedrooms and 2.5 bathrooms. - it last sold on September 13, 1990 for $569,000. Based on Redfin's Chappaqua data, we estimate the home's value is $1,662,036.

Single-familyProperty Type

1979Year Built

1 acresLot Size

$581Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,662,036

$1.1M since sold in September 1990$18K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 3.8% higher than the average sale price ($1.60M) of 6 comparable homes.

SOLD JUN 29, 2026
$1,609,031
A
4 beds2.5 baths2,443 sq ft
6 Killington St, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD SEP 24, 2026
$2,020,000
B
4 beds3.5 baths3,124 sq ft
4 Old House Ln, 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 SEP 16, 2026
$1,300,014
D
4 beds2.5 baths2,982 sq ft
49 E Ridge Ln, Mount Kisco, NY 10549
Listing by Berkshire Hathaway HS NY Prop
SOLD JUN 15, 2026
$1,630,000
E
4 beds2.5 baths2,460 sq ft
114 Old Lyme Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JUL 2, 2026
$1,862,500
F
4 beds3 baths3,002 sq ft
95 Old Lyme Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.

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Sell

$1,564,550

Est. take-home

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Est. cash available

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Rent

$4,950/mo

Redfin rental estimate

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Market trends in 10514, NY

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

113.7%

0.2% MoM

Median sale price

$1.7M

$10K MoM

Avg. days on market

17d

0 days MoM

Recently sold homes

9 MoM

New listings for sale

$1,349,000
3 beds3.5 baths2,595 sq ft
7 Cabin Ridge Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
$3,299,000
5 beds6 baths7,597 sq ft
46 Annandale Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
$2,349,000
5 beds5.5 baths5,646 sq ft
48 Random Farms Cir, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
$3,088,000
7 beds7 baths5,345 sq ft
301 Roaring Brook Rd, Chappaqua, NY 10514
Listing by EXP Realty
See all

Provided by Redfin

Sale history for 5 Whippoorwill Lake Rd

Year

Property tax

Land + Additions

Assessment*

2026

$29,002 (+0.3%)

$50,000 + $144,200

$194,200

2025

$28,928 (+2.2%)

$50,000 + $144,200

$194,200

2024

$28,315 (+2.8%)

$50,000 + $144,200

$194,200

2023

$27,557 (−4.4%)

$50,000 + $144,200

$194,200

2022

$28,820 (+1.1%)

$50,000 + $144,200

$194,200

2021

$28,493 (+9.4%)

$50,000 + $144,200

$194,200

2020

$26,051 (+1.5%)

$50,000 + $144,200

$194,200

2019

$25,656

$50,000 + $144,200

$194,200

2018

$50,000 + $144,200

$194,200

2017

$50,000 + $144,200

$194,200

2016

$50,000 + $144,200

$194,200

2014

$50,000 + $144,200

$194,200

2013

$50,000 + $144,200

$194,200

2012

$50,000 + $144,200

$194,200

2011

$50,000 + $144,200

$194,200

2010

$50,000 + $144,200

$194,200

2009

$50,000 + $144,200

$194,200

2008

$50,000 + $144,200

$194,200

Tax history for 5 Whippoorwill Lake Rd

Year

Property tax

Land + Additions

Assessment*

2026

$29,002 (+0.3%)

$50,000 + $144,200

$194,200

2025

$28,928 (+2.2%)

$50,000 + $144,200

$194,200

2024

$28,315 (+2.8%)

$50,000 + $144,200

$194,200

2023

$27,557 (−4.4%)

$50,000 + $144,200

$194,200

2022

$28,820 (+1.1%)

$50,000 + $144,200

$194,200

2021

$28,493 (+9.4%)

$50,000 + $144,200

$194,200

2020

$26,051 (+1.5%)

$50,000 + $144,200

$194,200

2019

$25,656

$50,000 + $144,200

$194,200

2018

$50,000 + $144,200

$194,200

2017

$50,000 + $144,200

$194,200

2016

$50,000 + $144,200

$194,200

2014

$50,000 + $144,200

$194,200

2013

$50,000 + $144,200

$194,200

2012

$50,000 + $144,200

$194,200

2011

$50,000 + $144,200

$194,200

2010

$50,000 + $144,200

$194,200

2009

$50,000 + $144,200

$194,200

2008

$50,000 + $144,200

$194,200

*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: 2
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Hot Water Steam

Fireplace Information
# of Fireplaces: 2
Has Fireplace

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Contemporary
Exterior Wall: Frame Wood

Property Information
Subdivision Name: WHIPPOORWILL LAKE
Living Sq. Ft: 2,863
Ground Floor Sq. Ft: 1,646
Building Sq. Ft: 2,863

Parking & Garage Information
# of Parking Spaces: 2
Parking Type: Basement Garage
Garage / Carport Type: Basement

Lot Information
# of Buildings: 1
Land Sq. Ft: 43,414
Legal Lot Number: 2
Legal Block Number: 1
School Tax District: CHAPPAQUA
Municipality Name: NEW CASTLE
Acres: 0.9966
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: 2.5
Sq. Ft.: 2,863
Stories: —
Lot Size: 1 acres
Style: Single Family Residential
Year Built: 1979
Year Renovated: —
County: Westchester County
APN: 553600A10100600010020000000

Home facts updated by county records on Sep 25, 2026

Around this home

Schools

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 • 1.6mi

9/10

Horace Greeley High School

Public 9-12 • 1.1mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

4/10 Flood Factor

Estimated 11-17% chance 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 4.3 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

$1.58M – $1.91M

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Nearby similar homes

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Land— sq ft

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New listings for sale in 10514

$1,349,000

3 beds3.5 baths2,595 sq ft

7 Cabin Ridge Rd, Chappaqua, NY 10514

Listing by William Raveis-New York, LLC

$3,299,000

5 beds6 baths7,597 sq ft

46 Annandale Rd, Chappaqua, NY 10514

Listing by Compass Greater NY, LLC

$2,349,000

5 beds5.5 baths5,646 sq ft

48 Random Farms Cir, Chappaqua, NY 10514

Listing by Compass Greater NY, LLC

$3,088,000

7 beds7 baths5,345 sq ft

301 Roaring Brook Rd, Chappaqua, NY 10514

Listing by EXP Realty

Home values near 5 Whippoorwill Lake Rd

Data from public records.

Address	Redfin Estimate
33 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 4.5 Baths \| 5201 Sq. Ft.	$2,135,146
10 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3706 Sq. Ft.	$1,855,367

Address	Redfin Estimate
14 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 4 Baths \| 6990 Sq. Ft.	$2,889,396
6 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3244 Sq. Ft.	$2,057,706

Address	Redfin Estimate
44 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 3 Baths \| 4471 Sq. Ft.	$1,818,505
40 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 4 Baths \| 5182 Sq. Ft.	$2,131,234

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