Google street view image for 345 Whippoorwill Rd, Chappaqua, NY 10514

Off market jul 2012 for $1.3M

$2,857,109

Est. refi paymentEst. refi $9,834/mo

•

6.5 ba

•

5,350

sq ft

345 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Spectacular setting with magnificent views and property in one of Chappaqua's most prestigious areas. Over 5000 square feet of flexible space including six BR's, six baths and a lovely spacious 20 year young private apartment perfect for the needs of a multigenerational family, guests, or staff. Originally part of the Glazier Estate, this distinctive home and property abut the 40 acre Glazier Arboretum.

Single-familyProperty Type

1958Year Built

2.58 acresLot Size

$534Est. Price/Sq.Ft.

2 spacesParking

Listing by • Douglas Elliman Real Estate

Bought with • William Raveis New York, LLC

Redfin checked: over 7 days ago

•Source:HGMLS #3120781

Redfin Estimate

$2,857,109

$1.6M since sold in July 2012$63K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15.9% higher than the average sale price ($2.46M) 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 AUG 3, 2026
$2,530,000
C
6 beds5 baths5,811 sq ft
17 Wampus Lake Dr, Armonk, NY 10504
Listing by Compass Greater NY, LLC
SOLD OCT 23, 2026
$3,389,000
D
4 beds6.5 baths5,563 sq ft
40 Algonquin Dr, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD SEP 2, 2026
$1,484,000
E
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
F
4 beds6 baths5,536 sq ft
211 Bedford Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC

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Earn from this home

Sell

$2,002,026

Est. take-home

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Refinance

Est. cash available

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Rent

$6,346/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 345 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$49,002 (+0.2%)

$150,000 + $174,500

$324,500

2025

$48,888 (+2.0%)

$150,000 + $174,500

$324,500

2024

$47,926 (+2.4%)

$150,000 + $174,500

$324,500

2023

$46,786 (−8.1%)

$150,000 + $174,500

$324,500

2022

$50,911 (+1.1%)

$150,000 + $174,500

$324,500

2021

$50,380 (+1.6%)

$150,000 + $174,500

$324,500

2020

$49,597 (+1.4%)

$150,000 + $174,500

$324,500

2019

$48,937

$150,000 + $174,500

$324,500

2018

$150,000 + $174,500

$324,500

2017

$150,000 + $174,500

$324,500

2016

$150,000 + $174,500

$324,500

2014

$150,000 + $154,755

$304,755

2013

$150,000 + $154,755

$304,755

2012

$150,000 + $154,755

$304,755

2011

$150,000 + $154,755

$304,755

2010

$150,000 + $250,000

$400,000

2009

$150,000 + $250,000

$400,000

2008

$150,000 + $250,000

$400,000

Tax history for 345 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$49,002 (+0.2%)

$150,000 + $174,500

$324,500

2025

$48,888 (+2.0%)

$150,000 + $174,500

$324,500

2024

$47,926 (+2.4%)

$150,000 + $174,500

$324,500

2023

$46,786 (−8.1%)

$150,000 + $174,500

$324,500

2022

$50,911 (+1.1%)

$150,000 + $174,500

$324,500

2021

$50,380 (+1.6%)

$150,000 + $174,500

$324,500

2020

$49,597 (+1.4%)

$150,000 + $174,500

$324,500

2019

$48,937

$150,000 + $174,500

$324,500

2018

$150,000 + $174,500

$324,500

2017

$150,000 + $174,500

$324,500

2016

$150,000 + $174,500

$324,500

2014

$150,000 + $154,755

$304,755

2013

$150,000 + $154,755

$304,755

2012

$150,000 + $154,755

$304,755

2011

$150,000 + $154,755

$304,755

2010

$150,000 + $250,000

$400,000

2009

$150,000 + $250,000

$400,000

2008

$150,000 + $250,000

$400,000

*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

5.5

Stories

—

Lot width

—

Lot depth

—

Lot size

2.58 Acres

Year renovated

—

Sq. Ft.

6,076

Year built

1958

Style

Single Family Residential

County

Westchester County

APN

553600A10101000020130000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking Information
2 Car (Detached), Other (See Remarks)

Interior

Bathroom Information
# of Baths (Full): 6
# of Baths (1/2): 1

Interior Features
# of Fireplaces: 1
Attic: Pull-Stairs

Cooling & Heating
A/C: Central
Heating: Hot Water, Hot Air

Room Information
# of Finished Rooms (Total): 12

Room 1 Information
Room Level: 1
Room Description: EH,LR/Fpl,Sunrm,EIK,Pwdrm,MBr/DrsRm/Bth,Study/WIC,Breezeway/SGDs to Courtyard. APT:EH,LR/DA/BrA,EIK/SGD to Patio,Bath/Lndry

Room 2 Information
Room Level: 2
Room Description: BR/Bath/BR. Separate Stairs to BR/WIC/Bth, BR/Bath

Room 3 Information
Room Description: BR/Bth/Dr. to patio,Utils. Htd.Work Room/Dr.out/Storage

Exterior

Building Information
Clapboard

Property Information
Property Sub-Type: Detached
Amenities: 1st Floor Master Bedroom, Legal Access Apartments, Close to Park, Patio, Privacy, View, Walk-In Closet, Walk-Out Basement
Included: B/I Shelves, Ceiling Fan, Dishwasher, Front Gate, Oven/Range, Refrigerator, Second Dishwasher, Second Stove, Wall to Wall Carpet

Lot Information
Sq. Ft. (Total): 5,350
Lot Size Area: 2.5820
Zoning: R2A

Financial

Tax Information
Tax Year: 2010
Municipality
Tax Amount: $41,979

Utilities

Utility Information
Heating Fuel: Oil
Sewer: Septic
Water Description: Municipal
Electric Company: Con-Edison

Waste Management Information
Garbage: Public

Location

School Information
School District: Chappaqua
Elementary School: Douglas G. Grafflin
Junior Middle High School: Robert E. Bell
High School: Horace Greeley

Location Information
Village: None
City: New Castle
County/Parish: Westchester County
Post Office: Chappaqua

Public facts

Beds: 6
Baths: 5.5
Sq. Ft.: 6,076
Stories: —
Lot Size: 2.58 acres
Style: Single Family Residential
Year Built: 1958
Year Renovated: —
County: Westchester County
APN: 553600A10101000020130000000

Home facts updated by county records on Sep 25, 2026

Other

Information for Agents
Negotiate Through: Listing Agent

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 • 0.9mi

10/10

Robert E Bell School

Public 5-8 • 1.6mi

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

$2.72M – $3.29M

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New listings for sale in 10514

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Home values near 345 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
365 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 6 Baths \| 6074 Sq. Ft.	$3,465,989
311 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 5 Baths \| 5234 Sq. Ft.	$2,711,893
360 Whippoorwill Rd, Chappaqua, NY 3 Beds \| 1 Baths \| 2064 Sq. Ft.	$1,598,136
320 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5 Baths \| 6058 Sq. Ft.	$4,987,704
340 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3184 Sq. Ft.	$2,426,380
6 Sutton Farm Dr, Chappaqua, NY 4 Beds \| 5.5 Baths \| 5612 Sq. Ft.	$3,222,906
2 Sutton Farm Dr, Chappaqua, NY 5 Beds \| 5 Baths \| 6914 Sq. Ft.	$3,061,984

Address	Redfin Estimate
354 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5 Baths \| 4926 Sq. Ft.	$2,156,931
335 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 7 Baths \| 5566 Sq. Ft.	$3,930,441
341 Whippoorwill Rd, Chappaqua, NY 7 Beds \| 9 Baths \| 9664 Sq. Ft.	$7,712,108
321 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5.5 Baths \| 5195 Sq. Ft.	$3,149,192
350 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 4 Baths \| 4698 Sq. Ft.	$2,558,494
1 Sutton Farm Dr, Chappaqua, NY 5 Beds \| 6 Baths \| 7200 Sq. Ft.	$4,223,286
78 Carolyn Pl, Chappaqua, NY 5 Beds \| 5.5 Baths \| 7593 Sq. Ft.	$3,330,827

Address	Redfin Estimate
344 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5 Baths \| 6450 Sq. Ft.	$3,701,737
351 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 7 Baths \| 8244 Sq. Ft.	$4,128,018
363 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3450 Sq. Ft.	$1,676,512
331 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 4.5 Baths \| 4130 Sq. Ft.	$2,071,313
11 Sutton Farm Dr, Chappaqua, NY 5 Beds \| 6 Baths \| 5855 Sq. Ft.	$3,387,402
10 Sutton Farm Dr, Chappaqua, NY 4 Beds \| 7 Baths \| 9605 Sq. Ft.	$3,873,858
63 Carolyn Pl, Chappaqua, NY 4 Beds \| 6 Baths \| 7286 Sq. Ft.	$3,109,414

Property information provided by HGMLS when last listed in 2011. This data may not match . Learn more.

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