209 Whippoorwill Rd, Chappaqua, NY 10514

Off market sep 2013 for $1.4M

$2,443,684

Est. refi paymentEst. refi $10,189/mo

•

6,993

sq ft

209 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Crowning an expansive, private lot in prestigious Whippoorwill this classic gated contemporary is the epitome of peaceful seclusion! The exterior of this meticulously maintained home is timeless expression; a lush fusion of mature trees, & greenery overlooking WCC golf course. Inside, open floor plan flows with an easy, relaxed elegance. Home or country retreat, amenities include entertainers kitchen, luxury spa master and generous LL walk-out quarters for Au-pair and/or extended stay guests! Additional Information: ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1974Year Built

5.88 acresLot Size

$349Est. Price/Sq.Ft.

2 spacesParking

Listing by Beth Silfen • Houlihan Lawrence Inc.

Listing by Todd Goddard • Houlihan Lawrence Inc.

Bought with Rebecca Berman • Douglas Elliman Real Estate

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H3307817

Redfin Estimate

$2,443,684

$1.0M since sold in September 2013$3,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.4% lower than the average sale price ($2.61M) of 6 comparable homes.

SOLD JUN 15, 2026
$4,000,000
A
4 beds4 baths4,236 sq ft
12 Haights Cross Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
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 JUL 14, 2026
$2,500,000
C
4 beds4.5 baths5,012 sq ft
15 Haights Cross Rd, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD OCT 30, 2026
$2,700,000
D
4 beds3.5 baths4,461 sq ft
10 Crestview Dr, Pleasantville, NY 10570
Listing by Julia B Fee Sothebys Int. Rlty
SOLD DEC 26, 2025
$2,960,000
E
4 beds4.5 baths6,542 sq ft
93 Haights Cross Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD SEP 24, 2026
$2,020,000
F
4 beds3.5 baths3,124 sq ft
4 Old House Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.

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Sell

$1,512,332

Est. take-home

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Est. cash available

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Rent

$5,761/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 209 Whippoorwill Rd

Date

Event

Price

HGMLS #3307817

Mar 14, 2014

Price Changed

$1,410,000

$202/sq ft

Sep 27, 2013

Sold

$1,410,000

$202/sq ft

Sep 24, 2013

Delisted

—

Aug 20, 2013

Contingent

—

Aug 20, 2013

Price Changed

$1,495,000

$214/sq ft

Jul 24, 2013

Price Changed

$1,495,000

$214/sq ft

May 8, 2013

Price Changed

$1,649,000

$236/sq ft

Mar 18, 2013

Listed

$1,795,000

$257/sq ft

HGMLS #3208457

Apr 7, 2014

Price Changed

$1,430,000

$204/sq ft

Mar 14, 2014

Price Changed

$1,530,000

$219/sq ft

Dec 19, 2012

Sold

$1,530,000

$219/sq ft

Nov 20, 2012

Delisted

—

Sep 12, 2012

Price Changed

$1,430,000

$204/sq ft

May 29, 2012

Price Changed

$1,585,000

$227/sq ft

Apr 30, 2012

Price Changed

$1,675,000

$240/sq ft

Mar 16, 2012

Listed

$1,795,000

$257/sq ft

Brilliantly presented. Preservation of period finishes reminiscent of mid-century modern aesthetics. Whole house renovation; Newer efficient doors & windows. Newer heating, A/C & hot water systems. Newer roof. Refinished wood & travertine floors. Deluxe amenities; professional kitchen w/ high-end appliances, luxurious master bath sauna & steam shower, whole-house sound system & gym. 3 fireplaces. Additional 1000+ finished lower level walk-out. All complimented by 5+ acres in Whippoorwill enclave.

OneKey® MLS as Distributed by MLS Grid #H3307817

Sep 27, 2013

Sold

$1,410,000

$202/sq ft

Mar 18, 2013

Listed

$1,495,000

$214/sq ft

Public Records

Feb 1, 2013

Sold

$1,530,000

$219/sq ft

OneKey® MLS as Distributed by MLS Grid #H3208457

Dec 19, 2012

Sold

$1,530,000

$219/sq ft

Mar 16, 2012

Listed

$1,430,000

$204/sq ft

Public Records

Jul 6, 2006

Sold

$1,650,000

$236/sq ft

Public Records

Oct 12, 2004

Sold

$1,620,000

$232/sq ft

Public Records

Jan 5, 1988

Sold

$1,125,000

$161/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$50,910 (+0.2%)

$200,000 + $104,880

$304,880

2025

$50,805 (+1.9%)

$200,000 + $104,880

$304,880

2024

$49,868 (+2.4%)

$200,000 + $104,880

$304,880

2023

$48,691 (+2.3%)

$200,000 + $104,880

$304,880

2022

$47,617 (+1.0%)

$200,000 + $104,880

$304,880

2021

$47,154 (+1.6%)

$200,000 + $104,880

$304,880

2020

$46,418 (+1.4%)

$200,000 + $104,880

$304,880

2019

$45,798

$200,000 + $104,880

$304,880

2018

$200,000 + $104,880

$304,880

2017

$200,000 + $104,880

$304,880

2016

$200,000 + $104,880

$304,880

2014

$200,000 + $121,600

$321,600

2013

$200,000 + $121,600

$321,600

2012

$200,000 + $121,600

$321,600

2011

$200,000 + $121,600

$321,600

2010

$200,000 + $121,600

$321,600

2009

$200,000 + $121,600

$321,600

2008

$200,000 + $121,600

$321,600

Tax history for 209 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$50,910 (+0.2%)

$200,000 + $104,880

$304,880

2025

$50,805 (+1.9%)

$200,000 + $104,880

$304,880

2024

$49,868 (+2.4%)

$200,000 + $104,880

$304,880

2023

$48,691 (+2.3%)

$200,000 + $104,880

$304,880

2022

$47,617 (+1.0%)

$200,000 + $104,880

$304,880

2021

$47,154 (+1.6%)

$200,000 + $104,880

$304,880

2020

$46,418 (+1.4%)

$200,000 + $104,880

$304,880

2019

$45,798

$200,000 + $104,880

$304,880

2018

$200,000 + $104,880

$304,880

2017

$200,000 + $104,880

$304,880

2016

$200,000 + $104,880

$304,880

2014

$200,000 + $121,600

$321,600

2013

$200,000 + $121,600

$321,600

2012

$200,000 + $121,600

$321,600

2011

$200,000 + $121,600

$321,600

2010

$200,000 + $121,600

$321,600

2009

$200,000 + $121,600

$321,600

2008

$200,000 + $121,600

$321,600

*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

Stories

—

Lot width

—

Lot depth

—

Lot size

5.66 Acres

Year renovated

—

Sq. Ft.

6,993

Year built

1974

Style

Single Family Residential

County

Westchester County

APN

553600A10101800030090000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking Information
Carport YN: Yes
Carport Spaces: 2
Parking Total: 2
Parking Features: Attached, Carport

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1

Heating & Cooling
Cooling: Central Air
Heating: Hot Air, Oil

Interior Features
Interior Features: Cathedral Ceiling(s),Eat-in Kitchen,Formal Dining,Primary Bathroom,Walk-In Closet(s),Wet Bar
Levels: Two
Patio And Porch Features: Deck

Room Information
Basement YN: No
Rooms Total: 11
Basement: Walk-Out Access

Bathroom Information
Bathrooms Full: 3
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Wood Siding
Waterfront YN: No

Lot Information
Zoning: R-2A

Property Information
Stories: 2
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2013
Tax Source: Municipality
Tax Annual Amount: $44,066

Financial Information
Buyer Financing: Conventional

Utilities

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

Location

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: Rt.117 or 120 to Whippoorwill Road #209. Just North of Whippoorwill Country Club
County Or Parish: Westchester County

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 6,993
Stories: —
Lot Size: 5.66 acres
Style: Single Family Residential
Year Built: 1974
Year Renovated: —
County: Westchester County
APN: 553600A10101800030090000000

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 • 1.0mi

10/10

Robert E Bell School

Public 5-8 • 1.8mi

9/10

Horace Greeley High School

Public 9-12 • 2.1mi

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

4/10 Heat Factor

6 days above 97° expected this year, 13 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

5 unhealthy days expected this year, 7 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

$2.32M – $2.81M

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Home values near 209 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
301 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 6.5 Baths \| 10594 Sq. Ft.	—
211 Whippoorwill Rd, Chappaqua, NY 6 Beds \| 3.5 Baths \| 3916 Sq. Ft.	$2,055,731
34 Frog Rock Rd, Armonk, NY 5 Beds \| 4 Baths \| 5702 Sq. Ft.	$2,261,823
29 Frog Rock Rd, Armonk, NY 4 Beds \| 5 Baths \| 4750 Sq. Ft.	$2,420,240
33 Carolyn Pl, Chappaqua, NY 5 Beds \| 6 Baths \| 9141 Sq. Ft.	$3,902,753
35 Frog Rock Rd, Armonk, NY 5 Beds \| 4.5 Baths \| 5151 Sq. Ft.	$2,168,312
14 Frog Rock Rd, Armonk, NY 4 Beds \| 4.5 Baths \| 4226 Sq. Ft.	$2,881,610

Address	Redfin Estimate
129 Whippoorwill Rd, Armonk, NY - Beds \| 2 Baths \| 2917 Sq. Ft.	$1,573,867
57 Whippoorwill Crossing, Armonk, NY 4 Beds \| 5.5 Baths \| 5434 Sq. Ft.	$2,549,615
59 Whippoorwill Crossing, Armonk, NY 3 Beds \| 3 Baths \| 4677 Sq. Ft.	$2,110,244
21 Frog Rock Rd, Armonk, NY 4 Beds \| 4 Baths \| 3504 Sq. Ft.	$1,838,640
49 Carolyn Pl, Chappaqua, NY 6 Beds \| 7 Baths \| 11097 Sq. Ft.	$4,132,764
61 Carolyn Pl, Chappaqua, NY 5 Beds \| 5.5 Baths \| 5907 Sq. Ft.	$3,076,850
26 Frog Rock Rd, Armonk, NY 3 Beds \| 3 Baths \| 4715 Sq. Ft.	$2,110,588

Address	Redfin Estimate
201 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 2 Baths \| 3318 Sq. Ft.	$1,841,192
27 Frog Rock Rd, Armonk, NY 5 Beds \| 6 Baths \| 4535 Sq. Ft.	$2,308,213
45 Carolyn Pl, Chappaqua, NY 5 Beds \| 8 Baths \| 8116 Sq. Ft.	$4,141,357
37 Carolyn Pl, Chappaqua, NY 7 Beds \| 8 Baths \| 9307 Sq. Ft.	$3,357,004
30 Frog Rock Rd, Armonk, NY 5 Beds \| 5.5 Baths \| 6169 Sq. Ft.	$2,762,775
12 Frog Rock Rd, Armonk, NY 4 Beds \| 4 Baths \| 5433 Sq. Ft.	$2,263,905
51 Carolyn Pl, Chappaqua, NY 5 Beds \| 6.5 Baths \| 9679 Sq. Ft.	$4,605,055

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2013. This data may not match . Learn more.

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