354 Whippoorwill Rd, Chappaqua, NY 10514

Off Market Sep 2020 for $1.2M

$2,006,283

Est. refi paymentEst. refi $9,348/mo

•

4,926

sq ft

354 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Enjoy a bucolic setting with stunning private property, Shoreline pool and a barn. 2 spectacular acres in the prestigious Whippoorwill neighborhood this home offers location, location location! Close to Whole Foods, Chappaqua & Armonk, everything is right nearby. Nearly 5000sf, this 5 bedroom home has great possibilities for someone who wants to update and make this a fabulous home. Featuring a first floor bedroom with ensuite bathroom, 3 fireplaces and multiple living spaces. Sunny and bright! Generator. A/C needs work. Being sold in As-Is condition. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1955Year Built

2 acresLot Size

$407Est. Price/Sq.Ft.

2 spacesParking

Listing by Amy Singer • Houlihan Lawrence Inc.

Bought with Janice Tanner • Houlihan Lawrence Inc.

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6023629

Redfin Estimate

$2,006,283

$781K since sold in September 2020$1,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.6% lower than the average sale price ($2.10M) of 6 comparable homes.

SOLD AUG 17, 2026
$2,032,500
A
5 beds5.5 baths6,108 sq ft
16 Carolyn Pl, Armonk, NY 10504
Listing by Houlihan Lawrence Inc.
SOLD JUL 14, 2026
$2,500,000
B
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
C
4 beds3.5 baths3,585 sq ft
67 Tripp St, Mount Kisco, NY 10549
Listing by Ginnel Real Estate
SOLD MAY 7, 2026
$2,850,000
D
4 beds6 baths5,536 sq ft
211 Bedford Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD AUG 13, 2026
$1,830,000
E
4 beds3 baths3,672 sq ft
734 King St, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JAN 20, 2026
$1,920,000
F
5 beds4.5 baths3,849 sq ft
73 Whippoorwill Lake Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC

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Earn from this home

Sell

$1,026,038

Est. take-home

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Refinance

Est. cash available

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Rent

$6,079/mo

Redfin rental estimate

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Market trends in 10514, NY

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

113.6%

0.2% MoM

Median sale price

$1.7M

$11K MoM

Avg. days on market

17d

0 days MoM

Recently sold homes

11 MoM

New listings for sale

COMING SOON
$2,299,000
5 beds4.5 baths4,661 sq ft
20 Hitching Post Ln, Chappaqua, NY 10514
Listing by William Raveis-New York LLC
NEW 1 DAY AGO
$679,000
4 beds2 baths2,464 sq ft
10 Paula Pl, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
$5,750,000
6 beds7.5 baths9,247 sq ft
24 Trails End, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
$1,399,000
3 beds3 baths2,821 sq ft
10 Deborah Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
$749,000
3 beds1.5 baths1,414 sq ft
27 Mill River Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
$1,725,000
4 beds3.5 baths3,581 sq ft
53 W Orchard Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
$1,800,000
4 beds3.5 baths2,913 sq ft
406 Bedford Rd, Chappaqua, NY 10514
Listing by Howard Hanna Rand Realty
See all

Provided by Redfin

Sale history for 354 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$39,795 (+0.2%)

$105,000 + $132,405

$237,405

2025

$39,709 (+1.9%)

$105,000 + $132,405

$237,405

2024

$38,969 (+2.4%)

$105,000 + $132,405

$237,405

2023

$38,048 (+2.3%)

$105,000 + $132,405

$237,405

2022

$37,195 (−8.3%)

$105,000 + $132,405

$237,405

2021

$40,545 (+1.6%)

$105,000 + $132,405

$237,405

2020

$39,914 (−23.8%)

$105,000 + $156,750

$261,750

2019

$52,362

$105,000 + $244,000

$349,000

2018

$105,000 + $244,000

$349,000

2017

$105,000 + $244,000

$349,000

2016

$105,000 + $244,000

$349,000

2014

$105,000 + $244,000

$349,000

2013

$105,000 + $244,000

$349,000

2012

$105,000 + $244,000

$349,000

2011

$105,000 + $244,000

$349,000

2010

$105,000 + $244,000

$349,000

2009

$105,000 + $244,000

$349,000

2008

$105,000 + $244,000

$349,000

Tax history for 354 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$39,795 (+0.2%)

$105,000 + $132,405

$237,405

2025

$39,709 (+1.9%)

$105,000 + $132,405

$237,405

2024

$38,969 (+2.4%)

$105,000 + $132,405

$237,405

2023

$38,048 (+2.3%)

$105,000 + $132,405

$237,405

2022

$37,195 (−8.3%)

$105,000 + $132,405

$237,405

2021

$40,545 (+1.6%)

$105,000 + $132,405

$237,405

2020

$39,914 (−23.8%)

$105,000 + $156,750

$261,750

2019

$52,362

$105,000 + $244,000

$349,000

2018

$105,000 + $244,000

$349,000

2017

$105,000 + $244,000

$349,000

2016

$105,000 + $244,000

$349,000

2014

$105,000 + $244,000

$349,000

2013

$105,000 + $244,000

$349,000

2012

$105,000 + $244,000

$349,000

2011

$105,000 + $244,000

$349,000

2010

$105,000 + $244,000

$349,000

2009

$105,000 + $244,000

$349,000

2008

$105,000 + $244,000

$349,000

*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

4.5

Stories

—

Lot width

—

Lot depth

—

Lot size

1.96 Acres

Year renovated

—

Sq. Ft.

5,042

Year built

1955

Style

Single Family Residential

County

Westchester County

APN

553600A10101000020070000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 30, 2026.

Property details

Parking

Parking Information
Parking Total: 2
Parking Features: Attached

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 3

Heating & Cooling
Cooling: None
Heating: Baseboard, Hot Water, Oil

Interior Features
Interior Features: First Floor Bedroom
Appliances: Indirect Water Heater
Flooring: Hardwood
Levels: Two
Patio And Porch Features: Patio

Room Information
Basement YN: Yes
Attic: Unfinished
Rooms Total: 11
Basement: Partial, Unfinished

Bathroom Information
Bathrooms Full: 4
Bathrooms Half: 2

Exterior

Exterior Features
Construction Materials: Clapboard, Frame
Other Structures: Barn(s), Outbuilding
Waterfront YN: No

Pool Information
Pool Features: In Ground

Lot Information
Lot Features: Near Shops

Property Information
Stories: 2
Living Area Source: Public Records
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2020
Tax Source: Other
Tax Annual Amount: $38,941

Financial Information
Buyer Financing: Cash

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: Whippoorwill Road to #354
County Or Parish: Westchester County

Community Information
Community Features: Park

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 5,042
Stories: —
Lot Size: 1.96 acres
Style: Single Family Residential
Year Built: 1955
Year Renovated: —
County: Westchester County
APN: 553600A10101000020070000000

Home facts updated by county records on Jul 30, 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 • 1.7mi

9/10

Horace Greeley High School

Public 9-12 • 1.6mi

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

24% 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

$1.91M – $2.31M

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Home values near 354 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
365 Whippoorwill Road, Chappaqua, NY 5 Beds \| 6 Baths \| 6074 Sq. Ft.	$3,484,792
360 Whippoorwill Road, Chappaqua, NY 3 Beds \| 1 Baths \| 2064 Sq. Ft.	$1,572,836

Address	Redfin Estimate
344 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5 Baths \| 6450 Sq. Ft.	$3,724,614
341 Whippoorwill Road, Chappaqua, NY 7 Beds \| 9 Baths \| 9664 Sq. Ft.	$7,985,370

Address	Redfin Estimate
351 Whippoorwill Road, Chappaqua, NY 5 Beds \| 7 Baths \| 8244 Sq. Ft.	$4,210,762
363 Whippoorwill Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3450 Sq. Ft.	$1,830,333

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2020. This data may not match . Learn more.

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