18 Whippoorwill Lake Rd, Chappaqua, NY 10514

Off market aug 2019 for $1.4M

$2,513,128

Est. refi paymentEst. refi $11,331/mo

•

6,800

sq ft

18 Whippoorwill Lake Rd, Chappaqua, NY 10514

About this home

Custom built Center Hall Colonial at an exceptional value sited on 2 park like acres with specimen trees/plantings and verdant lawns. Perfect flow with high ceilings, gleaming wood floors & cherry millwork throughout. Eat-in kitchen with Rutt cabinetry & high end appliances opens to the family room with river rock fireplace. Adjacent office with wall of built-ins. Second level: master suite with tray ceiling, sitting room, walk in his/her closets and spectacular lake views. Large marble bath with Jacuzzi tub, Additional bedrooms & baths and large bonus room for entertainment. Walk out lower level boasts exercise & recreation areas plus a complete au pair/in-law set up with kitchenette and full bath. Home sits on the glistening lake perfect for boating and fishing. Excellent location, close to new Whole Foods, train and schools. ***NOTE; As per Assessor's Office, Current List Price translates to a tax reduction of $8,434 resulting in taxes of $42,705 for fiscal year 2020. Additional Information: Amenities:Guest Quarters,Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,

Single-familyProperty Type

1996Year Built

1.91 acresLot Size

$370Est. Price/Sq.Ft.

3 spacesParking

Listing by Patricia Karr • Houlihan Lawrence Inc.

Bought with Cindy Glynn • William Raveis-New York, LLC

Redfin checked: a few seconds ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4927187

Redfin Estimate

$2,513,128

$1.0M since sold in August 2019$42K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.5% higher than the average sale price ($2.36M) of 6 comparable homes.

SOLD SEP 24, 2026
$2,020,000
A
4 beds3.5 baths3,124 sq ft
4 Old House Ln, 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 SEP 4, 2026
$3,175,000
C
4 beds5.5 baths9,284 sq ft
16 Taylor Rd, Mount Kisco, NY 10549
Listing by Houlihan Lawrence Inc.
SOLD AUG 4, 2026
$2,486,000
D
4 beds4.5 baths6,640 sq ft
17 Byram Meadows Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JAN 16, 2026
$2,300,000
E
4 beds5 baths4,981 sq ft
16 Club Way, Mount Kisco, NY 10549
Listing by Compass Greater NY, LLC
SOLD OCT 30, 2026
$2,700,000
F
4 beds3.5 baths4,461 sq ft
10 Crestview Dr, Pleasantville, NY 10570
Listing by Julia B Fee Sothebys Int. Rlty

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

Earn from this home

Sell

$1,344,790

Est. take-home

List your home with Redfin and save $25,131

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$6,335/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 18 Whippoorwill Lake Rd

Year

Property tax

Land + Additions

Assessment*

2026

$47,727 (+0.2%)

$75,000 + $210,560

$285,560

2025

$47,628 (+1.9%)

$75,000 + $210,560

$285,560

2024

$46,747 (+2.4%)

$75,000 + $210,560

$285,560

2023

$45,643 (+2.3%)

$75,000 + $210,560

$285,560

2022

$44,633 (+1.0%)

$75,000 + $210,560

$285,560

2021

$44,194 (+1.6%)

$75,000 + $210,560

$285,560

2020

$43,505 (−15.4%)

$75,000 + $210,560

$285,560

2019

$51,401

$75,000 + $210,560

$285,560

2018

$75,000 + $267,540

$342,540

2017

$75,000 + $267,540

$342,540

2016

$75,000 + $267,540

$342,540

2014

$75,000 + $267,540

$342,540

2013

$75,000 + $267,540

$342,540

2012

$75,000 + $267,540

$342,540

2011

$75,000 + $302,800

$377,800

2010

$75,000 + $302,800

$377,800

2009

$75,000 + $326,900

$401,900

2008

$75,000 + $326,900

$401,900

Tax history for 18 Whippoorwill Lake Rd

Year

Property tax

Land + Additions

Assessment*

2026

$47,727 (+0.2%)

$75,000 + $210,560

$285,560

2025

$47,628 (+1.9%)

$75,000 + $210,560

$285,560

2024

$46,747 (+2.4%)

$75,000 + $210,560

$285,560

2023

$45,643 (+2.3%)

$75,000 + $210,560

$285,560

2022

$44,633 (+1.0%)

$75,000 + $210,560

$285,560

2021

$44,194 (+1.6%)

$75,000 + $210,560

$285,560

2020

$43,505 (−15.4%)

$75,000 + $210,560

$285,560

2019

$51,401

$75,000 + $210,560

$285,560

2018

$75,000 + $267,540

$342,540

2017

$75,000 + $267,540

$342,540

2016

$75,000 + $267,540

$342,540

2014

$75,000 + $267,540

$342,540

2013

$75,000 + $267,540

$342,540

2012

$75,000 + $267,540

$342,540

2011

$75,000 + $302,800

$377,800

2010

$75,000 + $302,800

$377,800

2009

$75,000 + $326,900

$401,900

2008

$75,000 + $326,900

$401,900

*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

4.5

Stories

—

Lot width

—

Lot depth

—

Lot size

2.04 Acres

Year renovated

—

Sq. Ft.

5,170

Year built

1996

Style

Single Family Residential

County

Westchester County

APN

553600A10100600010070000000

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

Heating & Cooling
Cooling: Central Air
Heating: Baseboard, Hydro Air, Oil

Interior Features
Interior Features: Built-in Features,Cathedral Ceiling(s),Ceiling Fan(s),Eat-in Kitchen,Entertainment Cabinets,Entrance Foyer,Formal Dining,Marble Counters,Primary Bathroom,Pantry,Walk-In Closet(s)
Window Features: Blinds, Drapes, Screens, Storm Window(s)
Laundry Features: Inside
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Freezer, Microwave, Refrigerator, Washer, Oil Water Heater
Flooring: Hardwood
Levels: Three Or More
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Walkup
Rooms Total: 11
Basement: Finished, Walk-Out Access

Bathroom Information
Bathrooms Full: 4
Bathrooms Half: 1

Exterior

Exterior Features
Exterior Features: Gas Grill, Mailbox
Construction Materials: Frame, Shingle Siding, Wood Siding
Security Features: Fire Sprinkler System, Security System
Waterfront YN: Yes

Lot Information
Additional Parcels YN: No
Lot Features: Near School, Near Shops, Views

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

Financial

Tax Information
Tax Year: 2018
Tax Source: Municipality
Tax Annual Amount: $51,139

Financial Information
Buyer Financing: Conventional

Utilities

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

Location

HOA Information
Has Association
Association Fee 2: $1,200
Association Fee Includes: Common Area Maintenance

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

Public facts

Beds: 4
Baths: 4.5
Sq. Ft.: 5,170
Stories: —
Lot Size: 2.04 acres
Style: Single Family Residential
Year Built: 1996
Year Renovated: —
County: Westchester County
APN: 553600A10100600010070000000

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 • 1.6mi

9/10

Horace Greeley High School

Public 9-12 • 1.2mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

4/10 Flood Factor

Estimated 11-17% chance 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

6/10 Wind Factor

27% 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

$2.39M – $2.89M

Reach more buyers when you sell with Redfin. Save up to $25,131 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

NEW 31 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

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

$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.

$5,750,000

6 beds7.5 baths9,247 sq ft

24 Trails End, Chappaqua, NY 10514

Indoor sports court • Full home gym • Heated gunite pool

Listing by Compass Greater NY, 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 18 Whippoorwill Lake Rd

Data from public records.

Address	Redfin Estimate
33 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 4.5 Baths \| 5201 Sq. Ft.	$2,206,001
44 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 3 Baths \| 4471 Sq. Ft.	$1,875,281
6 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3244 Sq. Ft.	$2,004,182
52 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3347 Sq. Ft.	$2,182,370
371 Whippoorwill Road, Chappaqua, NY 5 Beds \| 4.5 Baths \| 6410 Sq. Ft.	$2,746,791
5 Whippoorwill Close, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3050 Sq. Ft.	$1,580,446
14 Berol Close, Chappaqua, NY 5 Beds \| 6.5 Baths \| 4243 Sq. Ft.	$2,541,845

Address	Redfin Estimate
5 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2863 Sq. Ft.	$1,622,055
10 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3706 Sq. Ft.	$1,811,907
40 Whippoorwill Lake Road, Chappaqua, NY 4 Beds \| 4 Baths \| 5182 Sq. Ft.	$2,166,477
2 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 4 Baths \| 2565 Sq. Ft.	$1,626,151
369 Whippoorwill Road, Chappaqua, NY 5 Beds \| 5.5 Baths \| 7391 Sq. Ft.	$4,015,141
370 Whippoorwill Road, Chappaqua, NY 6 Beds \| 3 Baths \| 7505 Sq. Ft.	$3,929,120
10 Berol Close, Chappaqua, NY 4 Beds \| 3.5 Baths \| 7571 Sq. Ft.	$2,176,939

Address	Redfin Estimate
14 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 4 Baths \| 6990 Sq. Ft.	$2,857,262
48 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 5697 Sq. Ft.	$2,564,198
41 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 3 Baths \| 6035 Sq. Ft.	$2,255,877
1 Whippoorwill Lake Road, Chappaqua, NY 5 Beds \| 2.5 Baths \| 3423 Sq. Ft.	$1,556,203
1 Berol Close, Chappaqua, NY 4 Beds \| 4 Baths \| 5385 Sq. Ft.	$2,719,908
97 Haights Cross Road, Chappaqua, NY 5 Beds \| 4 Baths \| 4143 Sq. Ft.	$2,701,110
6 Berol Close, Chappaqua, NY 4 Beds \| 5 Baths \| 5723 Sq. Ft.	$3,320,491

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

Minor Civil Divisions
Neighborhoods
Zip Codes
Cities
Popular Searches

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

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

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