400 Whippoorwill Rd, Chappaqua, NY 10514

Off market oct 2020 for $2.2M

$3,495,618

Est. refi paymentEst. refi $16,501/mo

•

6,600

sq ft

400 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Superbly crafted to flawlessly integrate timeless design with the finest upgrades & amenities, this brand new 5-bedroom Farmhouse-style Colonial sets the standard for luxury living. Constructed by a highly respected local builder on 1.52-acres in Chappaqua’s prestigious Whippoorwill area, meticulous attention to detail & quality is evident in every aspect of the residence. Expansive 6600-sf interior feature white oak floors, elegant mill work, radiant heated master bath, and 10-ft ceilings on main level & 9-ft ceilings on 2nd floor & walk-out lower level.The opportunity to choose finishing touches & customize to create your perfect home. State-of-the-art systems, transfer switch for future generator & pre-wired for “smart house” technologies. Maintenance-free Hardie Board exterior with handsome front porch & generous rear patio. Set back from the road on beautiful, level property with pool site. Sought-after location just minutes to Chappaqua Crossing; close to village & train. Additional Information: Amenities:Guest Quarters,Storage,ParkingFeatures:3 Car Attached,

Single-familyProperty Type

2020Year Built

1.52 acresLot Size

$530Est. Price/Sq.Ft.

3 spacesParking

Listing by Sharon Bodnar Briskman • Houlihan Lawrence Inc.

Bought with Mark Boyland • Keller Williams Realty Partner

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H5003722

Redfin Estimate

$3,495,618

$1.3M since sold in October 2020$75K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 24.7% higher than the average sale price ($2.80M) of 6 comparable homes.

SOLD SEP 4, 2026
$3,175,000
A
4 beds5.5 baths9,284 sq ft
16 Taylor Rd, Mount Kisco, NY 10549
Listing by Houlihan Lawrence Inc.
SOLD AUG 18, 2026
$2,900,000
B
5 beds5.5 baths7,238 sq ft
2 Heathcote Dr, Mount Kisco, NY 10549
Listing by Howard Hanna Rand Realty
SOLD SEP 24, 2026
$2,020,000
C
4 beds3.5 baths3,124 sq ft
4 Old House Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
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 OCT 9, 2026
$3,300,000
E
5 beds5.5 baths7,388 sq ft
15 Heritage Dr, Pleasantville, NY 10570
Listing by Serhant LLC
SOLD AUG 17, 2026
$2,032,500
F
5 beds5.5 baths6,108 sq ft
16 Carolyn Pl, Armonk, NY 10504
Listing by Houlihan Lawrence Inc.

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,742,885

Est. take-home

List your home with Redfin and save $34,956

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$6,517/mo

Redfin rental estimate

List your home for rent

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 400 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$71,383 (+0.2%)

$60,000 + $366,360

$426,360

2025

$71,222 (+1.9%)

$60,000 + $366,360

$426,360

2024

$69,888 (+2.5%)

$60,000 + $366,360

$426,360

2023

$68,202 (+2.3%)

$60,000 + $366,360

$426,360

2022

$66,650 (+124.0%)

$60,000 + $366,360

$426,360

2021

$29,757 (+227.4%)

$60,000 + $366,360

$426,360

2020

$9,088

$60,000 + $130,600

$190,600

2019

$9,088

$60,000

2018

$60,000

2017

$60,000

2016

$60,000

2014

$60,000

2013

$60,000

2012

$60,000

2011

$60,000

2010

$60,000

2009

$60,000

2008

$60,000

Tax history for 400 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$71,383 (+0.2%)

$60,000 + $366,360

$426,360

2025

$71,222 (+1.9%)

$60,000 + $366,360

$426,360

2024

$69,888 (+2.5%)

$60,000 + $366,360

$426,360

2023

$68,202 (+2.3%)

$60,000 + $366,360

$426,360

2022

$66,650 (+124.0%)

$60,000 + $366,360

$426,360

2021

$29,757 (+227.4%)

$60,000 + $366,360

$426,360

2020

$9,088

$60,000 + $130,600

$190,600

2019

$9,088

$60,000

2018

$60,000

2017

$60,000

2016

$60,000

2014

$60,000

2013

$60,000

2012

$60,000

2011

$60,000

2010

$60,000

2009

$60,000

2008

$60,000

*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

1.4 Acres

Year renovated

—

Sq. Ft.

4,670

Year built

2020

Style

Single Family Residential

County

Westchester County

APN

553600A09301700020060000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking Information
Parking Total: 3
Parking Features: Attached, Garage Door Opener

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1

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

Interior Features
Interior Features: Built-in Features,Central Vacuum,Eat-in Kitchen,Entrance Foyer,Formal Dining,Primary Bathroom,Pantry,Walk-In Closet(s)
Window Features: ENERGY STAR Qualified Windows, Screens, Storm Window(s)
Appliances: Wine Refrigerator
Flooring: Hardwood
Levels: Three Or More
Patio And Porch Features: Patio, Porch

Room Information
Basement YN: Yes
Attic: Walkup
Rooms Total: 9
Basement: Full, Walk-Out Access

Bathroom Information
Bathrooms Full: 5
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Frame, HardiPlank Type
Security Features: Security System
Waterfront YN: No

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

Property Information
Stories: 3
Living Area Source: Other
Property Sub Type: Single Family Residence
Property Condition: To Be Built

Financial

Tax Information
Tax Year: 2019
Tax Source: Municipality
Tax Annual Amount: $100

Financial Information
Buyer Financing: Cash

Utilities

Utility Information
Electric Company: Con-Edison
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: Property located on the left side of Whippoorwill Rd coming from Route 117..just past Stornowaye on the left ..Look for the Sign ...Please DO NOT enter or walk property. Call Sharon to arrange virtual showings at 914-329-8889
County Or Parish: Westchester County

Public facts

Beds: 5
Baths: 5.0
Sq. Ft.: 4,670
Stories: —
Lot Size: 1.4 acres
Style: Single Family Residential
Year Built: 2020
Year Renovated: —
County: Westchester County
APN: 553600A09301700020060000000

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 • 1.2mi

10/10

Robert E Bell School

Public 5-8 • 1.6mi

9/10

Horace Greeley High School

Public 9-12 • 0.7mi

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

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 4.2 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.32M – $4.02M

Reach more buyers when you sell with Redfin. Save up to $34,956 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

NEW 30 HRS AGO

$400,000

4 beds1 bath1,220 sq ft

86 Maple Ave, Mount Kisco, NY 10549

Colonial home • Great storage space • 6,525 sq ft lot

Listing by Coldwell Banker Realty

$959,000

3 beds2 baths1,581 sq ft

10 Horseshoe Rd, Mount Kisco, NY 10549

Private acre • One-level living • Renovated kitchen

Listing by Houlihan Lawrence Inc.

$669,000

3 beds2 baths2,211 sq ft

116 Carpenter Ave, Mount Kisco, NY 10549

Short walk to train • Local shops • Dining

Listing by Houlihan Lawrence Inc.

$2,249,000

3 beds4 baths6,115 sq ft

33 Greenbriar Dr, Chappaqua, NY 10514

Juliet balconies • Wolf gas stove • 0.93 acre lot

Listing by Houlihan Lawrence Inc.

VIDEO TOUR

$49,500,000

8 beds9 baths26,079 sq ft

Bedford Corners, NY 10549

Exceptional scale • Elegantly renovated • 2-acre zoning

Listing by William Raveis-New York LLC

$1,749,000

4 beds3.5 baths2,913 sq ft

406 Bedford Rd, Chappaqua, NY 10514

Classic stone wall • 1.06 acre lot • 2 garage spots

Listing by Howard Hanna Rand Realty

New listings for sale in 10514

COMING SOON

$1,825,000

4 beds3.5 baths3,164 sq ft

25 Helena Dr, Chappaqua, NY 10514

Custom paneling • Hardwood floors • Fireplace

Listing by William Raveis-New York, LLC

$799,000

2 beds2.5 baths1,244 sq ft

13 Deer Run, Chappaqua, NY 10514

Renovated condo • $625 HOA • Garage

Listing by Compass Greater NY, LLC

Home values near 400 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
404 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3556 Sq. Ft.	$2,033,310
390 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 4 Baths \| 5188 Sq. Ft.	$3,106,567
410 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 6 Baths \| 6241 Sq. Ft.	$2,887,956
15 Killington St, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2566 Sq. Ft.	$1,416,836
12 Jeffrey Ln, Chappaqua, NY 5 Beds \| 4.5 Baths \| 6367 Sq. Ft.	$2,275,409
25 Attitash St, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3912 Sq. Ft.	$1,986,277
6 Killington St, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2443 Sq. Ft.	$1,701,479

Address	Redfin Estimate
398 Whippoorwill Rd, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3312 Sq. Ft.	$1,844,295
414 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 3 Baths \| 4050 Sq. Ft.	$1,861,180
14 Killington St, Chappaqua, NY 3 Beds \| 3 Baths \| 4267 Sq. Ft.	$2,022,503
15 Stornowaye St, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4330 Sq. Ft.	$1,832,060
9 Killington St, Chappaqua, NY 3 Beds \| 3 Baths \| 2625 Sq. Ft.	$1,687,706
5 Stornowaye St, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4305 Sq. Ft.	$1,913,775
10 Killington St, Chappaqua, NY 3 Beds \| 2 Baths \| 1608 Sq. Ft.	$1,092,367

Address	Redfin Estimate
394 Whippoorwill Rd, Chappaqua, NY 6 Beds \| 3.5 Baths \| 4612 Sq. Ft.	$3,183,603
412 Whippoorwill Rd, Chappaqua, NY 5 Beds \| 5 Baths \| 4210 Sq. Ft.	$1,888,649
41 Jeffrey Ln, Chappaqua, NY 3 Beds \| 2.5 Baths \| 2613 Sq. Ft.	$1,400,475
45 Jeffrey Ln, Chappaqua, NY 4 Beds \| 3 Baths \| 2137 Sq. Ft.	$1,406,378
21 Stornowaye St, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3750 Sq. Ft.	$1,861,883
10 Stornowaye St, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3416 Sq. Ft.	$1,597,963
7 Killington St, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4792 Sq. Ft.	$1,959,264

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2019. This data may not match . Learn more.

More real estate resources

Cities
Neighborhoods
Zip Codes
Minor Civil Divisions
Popular Searches

Greenwich homes for sale
New York homes for sale
Stamford homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

10536 homes for sale
10562 homes for sale
10520 homes for sale
10598 homes for sale
10549 homes for sale

Wilton homes for sale
Teaneck Township homes for sale
Weston homes for sale
Mahwah Township homes for sale
New Canaan homes for sale

Houses for rent in New Castle	Agents near me	White Plains, NY homes for sale	New Castle Housing Market
Houses for sale near me	New York, NY homes for sale	Yonkers, NY homes for sale
Land for sale near me	Manhattan, NY homes for sale	Scarsdale, NY homes for sale
Open Houses near me	Rochester, NY homes for sale	New Castle Property Records
Condos for sale near me	Buffalo, NY homes for sale	NY New Listings

Hunterbrook-Huntersville homes for sale
Bedford homes for sale
Croton Heights homes for sale