335 Whippoorwill Rd, Chappaqua, NY 10514

Off Market Aug 2023 for $3.5M

$3,980,833

Est. refi paymentEst. refi $26,710/mo

•

5,566

sq ft

335 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Superb design and detail define this spectacular and quintessential modern home. Conceived by architect Keith Kroeger, and now substantially renovated, the house is simply beautiful and exudes a Malibu vibe. Walls of glass flood the open interior plan with brilliant natural light. White walls, black window frames and wide-plank oak floors provide a perfect palette for art and sculpture and the simple art of living. 14 foot ceilings soar above the the living room. The family room is open to the kitchen centered on a leather finish, 12-foot Copacabana granite island. The property is stunning; 6 acres of open and rolling lawn, and now includes a brand new 50-foot saltwater pool by Glengate. The 48-acre Glazier Arboretum adjoins-providing direct access to its network of hiking trails. Pristine, private, and pastoral, 335 Whippoorwill Road offers a unique combination of location, condition and sophistication that is so rarely available in Chappaqua. Additional Information: Amenities:Guest Quarters,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1983Year Built

6.19 acresLot Size

$715Est. Price/Sq.Ft.

2 spacesParking

Listing by David Turner • Compass Greater NY, LLC

Contact: (914) 953-6010

Bought with Patricia Carpenter • Corcoran Legends Realty

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6242895

Redfin Estimate

$3,980,833

$481K since sold in August 2023$30K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 44.6% higher than the average sale price ($2.75M) of 6 comparable homes.

SOLD AUG 3, 2026
$2,530,000
A
6 beds5 baths5,811 sq ft
17 Wampus Lake Dr, Armonk, NY 10504
Listing by Compass Greater NY, LLC
SOLD AUG 17, 2026
$2,032,500
B
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
C
4 beds4.5 baths5,012 sq ft
15 Haights Cross Rd, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD JUN 15, 2026
$4,000,000
D
4 beds4 baths4,236 sq ft
12 Haights Cross Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD DEC 18, 2025
$2,500,000
E
5 beds5.5 baths5,907 sq ft
61 Carolyn Pl, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD DEC 26, 2025
$2,960,000
F
4 beds4.5 baths6,542 sq ft
93 Haights Cross Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC

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Earn from this home

Sell

$1,112,248

Est. take-home

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Refinance

Est. cash available

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Rent

$6,568/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

NEW 3 HRS AGO
$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.
$1,575,000
4 beds2.5 baths2,376 sq ft
9 Lori Ln, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
$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 335 Whippoorwill Rd

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #H6242895

Aug 4, 2023

Sold

$3,500,000

$629/sq ft

Jun 16, 2023

Pending

—

Apr 17, 2023

Listed

$3,500,000

$629/sq ft

OneKey® MLS as Distributed by MLS Grid #H6060825

Dec 16, 2020

Sold

$3,100,000

$557/sq ft

Oct 26, 2020

Pending

—

Sep 22, 2020

Price Changed

$3,275,000

$588/sq ft

Aug 14, 2020

Listed

$3,475,000

$624/sq ft

Aug 10, 2020

Coming Soon

$3,475,000

$624/sq ft

Custom designed for the ultimate modern day living on one of Chappaqua’s most-sought after streets. Meticulous attention to detail is evident throughout – from the 14’ ceilings in the great room, to the sunlit rooms with walls of windows this home has perfected the definition of modern flow. A gourmet white Miele kitchen with expansive 5-seat island opens to a large family room. The upper level offers a luxurious master suite with dressing room and stunning master bath with radiant heating and rainfall shower. Each of the five bedrooms is accompanied by an en suite bathroom and high ceilings. Expansive guest suite with private entrance. Lush landscaping and broad lawns for countless activities across 6.2 acres bordering the 44-acre Glazier Arboretum for ultimate privacy. 335 Whippoorwill offers a level of character and luxury rarely found in the marketplace. Designed by renown architects, Kroeger Intinarelli. Prime Chappaqua location and just 45 minutes to the city! Additional Information: ParkingFeatures:2 Car Attached,

HGMLS #4542397

May 2, 2016

Price Changed

$1,500,000

$269/sq ft

May 2, 2016

Sold

$1,500,000

$269/sq ft

Mar 4, 2016

Contingent

—

Mar 4, 2016

Price Changed

$1,599,000

$287/sq ft

Sep 17, 2015

Listed

$1,599,000

$287/sq ft

Spectacular European Contemporary designed by renowned architect Keith Kroeger and enhanced by Bruce Bierman. Dramatic residence set amid stunning natural beauty in prized Whippoorwill estate area. 14 foot ceiings in living room, sleek and sophisticated kitchen, oversized master suite, five en-suite bedrooms, private office suite. Memorable entertaining on the expansive bluestone terrace. Incredible setting on 6.2 acres with room for pool bordering the 44-acre Glazier Arboretum. Minutes from Chappaqua town center, train and schools. Taxes successfully grieved. Assessment reduced from 420,000 to 376,937. New taxes will reflect new assessment April, 2016.

OneKey® MLS as Distributed by MLS Grid #H4542397

May 2, 2016

Sold

$1,500,000

$269/sq ft

Sep 17, 2015

Listed

$1,599,000

$287/sq ft

HGMLS #4416781

Sep 17, 2015

Delisted

—

May 30, 2014

Listed

OneKey® MLS as Distributed by MLS Grid #H4416781

Sep 17, 2015

Listing Removed

—

May 30, 2014

Listed

$1,949,000

$350/sq ft

HGMLS #3300780

Feb 28, 2014

Delisted

—

Jan 11, 2013

Listed

OneKey® MLS as Distributed by MLS Grid #H3300780

Feb 28, 2014

Listing Removed

—

Jan 11, 2013

Listed

$1,995,000

$358/sq ft

HGMLS #3209201

Oct 8, 2012

Delisted

—

Mar 23, 2012

Listed

OneKey® MLS as Distributed by MLS Grid #H3209201

Oct 7, 2012

Listing Removed

—

Mar 23, 2012

Listed

$2,275,000

$409/sq ft

HGMLS #3116365

Jan 1, 2012

Delisted

—

May 19, 2011

Listed

Public Records

Sep 13, 1995

Sold

$930,000

$167/sq ft

Public Records

Aug 26, 1983

Sold

$373,000

$67/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$81,981 (+0.2%)

$150,000 + $343,500

$493,500

2025

$81,823 (+1.9%)

$150,000 + $343,500

$493,500

2024

$80,332 (+3.9%)

$150,000 + $343,500

$493,500

2023

$77,306 (+2.2%)

$150,000 + $343,500

$493,500

2022

$75,639 (+67.1%)

$150,000 + $336,300

$486,300

2021

$45,257 (+1.6%)

$150,000 + $336,300

$486,300

2020

$44,551 (+1.4%)

$150,000 + $142,500

$292,500

2019

$43,956

$150,000 + $142,500

$292,500

2018

$150,000 + $142,500

$292,500

2017

$150,000 + $142,500

$292,500

2016

$150,000 + $142,500

$292,500

2014

$150,000 + $270,000

$420,000

2013

$150,000 + $270,000

$420,000

2012

$150,000 + $270,000

$420,000

2011

$150,000 + $270,000

$420,000

2010

$150,000 + $270,000

$420,000

2009

$150,000 + $270,000

$420,000

2008

$150,000 + $270,000

$420,000

Tax history for 335 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$81,981 (+0.2%)

$150,000 + $343,500

$493,500

2025

$81,823 (+1.9%)

$150,000 + $343,500

$493,500

2024

$80,332 (+3.9%)

$150,000 + $343,500

$493,500

2023

$77,306 (+2.2%)

$150,000 + $343,500

$493,500

2022

$75,639 (+67.1%)

$150,000 + $336,300

$486,300

2021

$45,257 (+1.6%)

$150,000 + $336,300

$486,300

2020

$44,551 (+1.4%)

$150,000 + $142,500

$292,500

2019

$43,956

$150,000 + $142,500

$292,500

2018

$150,000 + $142,500

$292,500

2017

$150,000 + $142,500

$292,500

2016

$150,000 + $142,500

$292,500

2014

$150,000 + $270,000

$420,000

2013

$150,000 + $270,000

$420,000

2012

$150,000 + $270,000

$420,000

2011

$150,000 + $270,000

$420,000

2010

$150,000 + $270,000

$420,000

2009

$150,000 + $270,000

$420,000

2008

$150,000 + $270,000

$420,000

*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

Stories

—

Lot width

—

Lot depth

—

Lot size

6.18 Acres

Year renovated

—

Sq. Ft.

5,566

Year built

1983

Style

Single Family Residential

County

Westchester County

APN

553600A10101400010020000000

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: 1

Heating & Cooling
Cooling: Central Air
Heating: Hydro Air, Propane

Interior Features
Interior Features: Cathedral Ceiling(s),Eat-in Kitchen,Entrance Foyer,Formal Dining,First Floor Bedroom,High Ceilings,Kitchen Island,Primary Bathroom,Open Kitchen
Window Features: Floor to Ceiling Windows, Oversized Windows, Wall of Windows
Appliances: Dryer, Refrigerator, Washer, Gas Water Heater

Room Information
Basement YN: No
Attic: None
Rooms Total: 11
Basement: None
Additional Rooms: Office

Bathroom Information
Bathrooms Full: 6
Bathrooms Half: 2

Exterior

Exterior Features
Construction Materials: Frame, Stucco
Fencing: Fenced
Waterfront YN: No

Pool Information
Pool Features: In Ground

Lot Information
Additional Parcels YN: No

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

Financial

Tax Information
Tax Year: 2023
Tax Source: Municipality
Tax Annual Amount: $75,638

Financial Information
Buyer Financing: Cash

Utilities

Utility Information
Sewer: Septic Tank
Utilities: Trash Collection Public

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: Whippoorwill Road to #335.
County Or Parish: Westchester County

Public facts

Beds: 5
Baths: 6.0
Sq. Ft.: 5,566
Stories: —
Lot Size: 6.18 acres
Style: Single Family Residential
Year Built: 1983
Year Renovated: —
County: Westchester County
APN: 553600A10101400010020000000

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 • 0.9mi

10/10

Robert E Bell School

Public 5-8 • 1.6mi

9/10

Horace Greeley High School

Public 9-12 • 1.7mi

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

7 days above 98° expected this year, 13 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

$3.78M – $4.58M

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Home values near 335 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
301 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 6.5 Baths \| 10594 Sq. Ft.	—
311 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 5 Baths \| 5234 Sq. Ft.	$2,692,865

Address	Redfin Estimate
354 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5 Baths \| 4926 Sq. Ft.	$2,006,283
351 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 7 Baths \| 8244 Sq. Ft.	$4,210,762

Address	Redfin Estimate
344 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5 Baths \| 6450 Sq. Ft.	$3,773,759
360 Whippoorwill Rd, Chappaqua, NY 3 Beds \| 1 Baths \| 2064 Sq. Ft.	$1,572,836

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2023. This data may not match . Learn more.

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