321 Whippoorwill Rd, Chappaqua, NY 10514

Off market jul 2024 for $3M

$3,149,192

Est. refi paymentEst. refi $22,676/mo

•

5,195

sq ft

321 Whippoorwill Rd, Chappaqua, NY 10514

About this home

This fully turn-key colonial exudes style and sophistication. Situated on over 2 acres of picturesque property, this special home has been meticulously renovated, maintained and designed with custom millwork throughout. First floor features a double height entry foyer, gourmet kitchen by DEANE, light filled living room, den/playroom, formal dining room, home office/ guest room, mudroom with custom built-ins and renovated full and half bath. The expansive upstairs includes a private primary suite with spacious custom bathroom, 3 additional bedrooms with adjoining updated bathrooms, laundry room and a second office/play area. Walk-out lower level with game room/den, gym, additional full bath and tons of storage. Relax and unwind in an outdoor paradise! Shoot some hoops on the newly installed sport court and then take a dip in the heated saltwater pool with jacuzzi and waterfall. Additional amenities include a full house generator, electric vehicle charger and more. Additional Information: Amenities:Marble Bath,Soaking Tub,Steam Shower,Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1992Year Built

2.04 acresLot Size

$606Est. Price/Sq.Ft.

2 spacesParking

Listing by Amanda Acard • Nestedge Realty

Listing by Joanna Cohan Winograd • Nestedge Realty

Contact: (914) 939-8800

Bought with Hillary Landau • Compass Greater NY, LLC

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6294126

Redfin Estimate

$3,149,192

$149K since sold in July 2024$47K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 37.5% higher than the average sale price ($2.29M) 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 DEC 18, 2025
$2,500,000
B
5 beds5.5 baths5,907 sq ft
61 Carolyn Pl, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
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 SEP 2, 2026
$1,484,000
D
4 beds3.5 baths3,585 sq ft
67 Tripp St, Mount Kisco, NY 10549
Listing by Ginnel Real Estate
SOLD OCT 30, 2026
$2,700,000
E
4 beds3.5 baths4,461 sq ft
10 Crestview Dr, Pleasantville, NY 10570
Listing by Julia B Fee Sothebys Int. Rlty
SOLD AUG 3, 2026
$2,530,000
F
6 beds5 baths5,811 sq ft
17 Wampus Lake Dr, Armonk, NY 10504
Listing by Compass Greater NY, LLC

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Sell

$666,344

Est. take-home

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Est. cash available

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Rent

$6,498/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 321 Whippoorwill Rd

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #H6294126

Jul 29, 2024

Sold

$3,000,000

$577/sq ft

Mar 28, 2024

Pending

—

Mar 21, 2024

Listed

$2,750,000

$529/sq ft

Mar 18, 2024

Coming Soon

$2,750,000

$529/sq ft

HGMLS #3301298

Mar 14, 2014

Price Changed

$1,800,000

$346/sq ft

Nov 15, 2013

Sold

$1,800,000

$346/sq ft

Sep 13, 2013

Delisted

—

Jul 13, 2013

Contingent

—

Jul 13, 2013

Price Changed

$1,850,000

$356/sq ft

Jun 17, 2013

Price Changed

$1,850,000

$356/sq ft

Apr 27, 2013

Relisted

—

Apr 19, 2013

Delisted

—

Feb 25, 2013

Price Changed

$1,999,000

$385/sq ft

Feb 25, 2013

Relisted

—

Jan 28, 2013

Delisted

—

Jan 14, 2013

Listed

$2,125,000

$409/sq ft

OneKey® MLS as Distributed by MLS Grid #H3301298

Nov 15, 2013

Sold

$1,800,000

$346/sq ft

Jan 14, 2013

Listed

$1,850,000

$356/sq ft

OneKey® MLS as Distributed by MLS Grid #H3230093

Jan 14, 2013

Listing Removed

—

Oct 11, 2012

Listed

$2,250,000

$433/sq ft

Public Records

Oct 23, 1992

Sold

$360,000

$69/sq ft

Public Records

Dec 27, 1988

Sold

$700,000

$135/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$50,139 (+0.2%)

$150,000 + $150,200

$300,200

2025

$50,035 (+1.9%)

$150,000 + $150,200

$300,200

2024

$49,112 (+2.4%)

$150,000 + $150,200

$300,200

2023

$47,953 (+2.3%)

$150,000 + $150,200

$300,200

2022

$46,894 (+1.0%)

$150,000 + $150,200

$300,200

2021

$46,437 (−23.0%)

$150,000 + $150,200

$300,200

2020

$60,311 (+1.4%)

$150,000 + $150,200

$300,200

2019

$59,503

$150,000 + $247,000

$397,000

2018

$150,000 + $247,000

$397,000

2017

$150,000 + $247,000

$397,000

2016

$150,000 + $247,000

$397,000

2014

$150,000 + $247,000

$397,000

2013

$150,000 + $247,000

$397,000

2012

$150,000 + $247,000

$397,000

2011

$150,000 + $247,000

$397,000

2010

$150,000 + $247,000

$397,000

2009

$150,000 + $247,000

$397,000

2008

$150,000 + $247,000

$397,000

Tax history for 321 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$50,139 (+0.2%)

$150,000 + $150,200

$300,200

2025

$50,035 (+1.9%)

$150,000 + $150,200

$300,200

2024

$49,112 (+2.4%)

$150,000 + $150,200

$300,200

2023

$47,953 (+2.3%)

$150,000 + $150,200

$300,200

2022

$46,894 (+1.0%)

$150,000 + $150,200

$300,200

2021

$46,437 (−23.0%)

$150,000 + $150,200

$300,200

2020

$60,311 (+1.4%)

$150,000 + $150,200

$300,200

2019

$59,503

$150,000 + $247,000

$397,000

2018

$150,000 + $247,000

$397,000

2017

$150,000 + $247,000

$397,000

2016

$150,000 + $247,000

$397,000

2014

$150,000 + $247,000

$397,000

2013

$150,000 + $247,000

$397,000

2012

$150,000 + $247,000

$397,000

2011

$150,000 + $247,000

$397,000

2010

$150,000 + $247,000

$397,000

2009

$150,000 + $247,000

$397,000

2008

$150,000 + $247,000

$397,000

*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

2.06 Acres

Year renovated

—

Sq. Ft.

5,195

Year built

1992

Style

Single Family Residential

County

Westchester County

APN

553600A10101400010040000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking Information
Parking Total: 2
Parking Features: Attached, Driveway, Electric Vehicle Charging Station(s)

Interior

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

Interior Features
Interior Features: Chefs Kitchen,Eat-in Kitchen,Formal Dining,High Ceilings,Kitchen Island,Primary Bathroom,Open Kitchen,Pantry,Walk-In Closet(s),Wet Bar
Appliances: Indirect Water Heater
Flooring: Hardwood
Levels: Three Or More
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Pull Stairs
Rooms Total: 12
Basement: Partially Finished, Walk-Out Access
Additional Rooms: Dining Area,Office

Bathroom Information
Bathrooms Full: 5
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Frame, Wood Siding
Fencing: Fenced
Security Features: Fire Sprinkler System, Security System
Waterfront YN: No

Pool Information
Pool Features: In Ground

Lot Information
Additional Parcels YN: No
Lot Features: Near School, Near Shops, Sprinklers In Front, Sprinklers In Rear

Property Information
Stories: 3
Living Area Source: Public Records
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2023
Tax Source: Municipality
Tax Annual Amount: $47,953

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
County Or Parish: Westchester County

Community Information
Community Features: Park

Public facts

Beds: 5
Baths: 5.0
Sq. Ft.: 5,195
Stories: —
Lot Size: 2.06 acres
Style: Single Family Residential
Year Built: 1992
Year Renovated: —
County: Westchester County
APN: 553600A10101400010040000000

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 • 0.9mi

10/10

Robert E Bell School

Public 5-8 • 1.7mi

9/10

Horace Greeley High School

Public 9-12 • 1.8mi

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, 14 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

$2.99M – $3.62M

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Home values near 321 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
301 Whippoorwill Road, Chappaqua, NY 5 Beds \| 6.5 Baths \| 10594 Sq. Ft.	—
335 Whippoorwill Road, Chappaqua, NY 5 Beds \| 7 Baths \| 5566 Sq. Ft.	$3,930,441
341 Whippoorwill Road, Chappaqua, NY 7 Beds \| 9 Baths \| 9664 Sq. Ft.	$7,712,108
345 Whippoorwill Road, Chappaqua, NY 6 Beds \| 6.5 Baths \| 5350 Sq. Ft.	$2,857,109
78 Carolyn Place, Chappaqua, NY 5 Beds \| 5.5 Baths \| 7593 Sq. Ft.	$3,330,827
59 Carolyn Place, Chappaqua, NY 5 Beds \| 6 Baths \| 7775 Sq. Ft.	$3,944,287
61 Carolyn Place, Chappaqua, NY 5 Beds \| 5.5 Baths \| 5907 Sq. Ft.	$3,076,850

Address	Redfin Estimate
344 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5 Baths \| 6450 Sq. Ft.	$3,701,737
351 Whippoorwill Road, Chappaqua, NY 5 Beds \| 7 Baths \| 8244 Sq. Ft.	$4,128,018
320 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5 Baths \| 6058 Sq. Ft.	$4,987,704
340 Whippoorwill Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3184 Sq. Ft.	$2,426,380
9 Bessel Lane, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4843 Sq. Ft.	$3,443,898
82 Carolyn Place, Chappaqua, NY 4 Beds \| 5.5 Baths \| 6662 Sq. Ft.	$2,860,281
65 Carolyn Place, Chappaqua, NY 5 Beds \| 4 Baths \| 6713 Sq. Ft.	$2,998,816

Address	Redfin Estimate
311 Whippoorwill Road, Chappaqua, NY 4 Beds \| 5 Baths \| 5234 Sq. Ft.	$2,711,893
211 Whippoorwill Road, Chappaqua, NY 6 Beds \| 3.5 Baths \| 3916 Sq. Ft.	$2,055,731
331 Whippoorwill Road, Chappaqua, NY 5 Beds \| 4.5 Baths \| 4130 Sq. Ft.	$2,071,313
350 Whippoorwill Road, Chappaqua, NY 4 Beds \| 4 Baths \| 4698 Sq. Ft.	$2,558,494
63 Carolyn Place, Chappaqua, NY 4 Beds \| 6 Baths \| 7286 Sq. Ft.	$3,109,414
2 Wildcat Road, Chappaqua, NY 5 Beds \| 4 Baths \| 5104 Sq. Ft.	$2,325,424
71 Carolyn Place, Chappaqua, NY 5 Beds \| 7.5 Baths \| 8204 Sq. Ft.	$4,786,721

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2024. This data may not match . Learn more.

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