369 Whippoorwill Rd, Chappaqua, NY 10514

Off Market Jun 2024 for $4M

$4,133,059

Est. refi paymentEst. refi $30,026/mo

•

7,391

sq ft

369 Whippoorwill Rd, Chappaqua, NY 10514

About this home

Updated Farmhouse Colonial embraces country life with its warmth and character yet infuses sophisticated, modern vibes at every turn. Reclaimed beams and wood accents are abundant along with exquisite designer lighting, designer wall coverings and wide board white oak floors underfoot. The formal rooms segue to casual living spaces with a bright, open kitchen at the hub for effortless entertaining. Upstairs offers a private primary suite with dressing room and a spa bath. A Jack-and-Jill bedroom suite, bedroom with bath, and a large loft space with den, bedroom, bath and laundry, complete the upper level. An extraordinary, two-story cabana room with its barreled ceiling, abundant windows and summer kitchen flows seamlessly to the outdoors with a built-in grill, an extensive patio, heated pool with spa and a golf green. Top this off with lush specimen plantings on a level, 2-acre property, steps from the hiking trails at Glazier Preserve, close to towns and trains, and you have the perfect solution turning the everyday into extraordinary. Additional Information: Amenities:Soaking Tub,Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,

Single-familyProperty Type

1994Year Built

2.21 acresLot Size

$559Est. Price/Sq.Ft.

3 spacesParking

Listing by Brian Milton • Compass Greater NY, LLC

Contact: (914) 469-9889

Bought with Sari Shaw • Compass Greater NY, LLC

Redfin checked: a minute ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6305280

Redfin Estimate

$4,133,059

$128K since sold in June 2024$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 54.4% higher than the average sale price ($2.68M) 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 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 DEC 18, 2025
$2,500,000
C
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
D
4 beds4.5 baths5,012 sq ft
15 Haights Cross Rd, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
SOLD AUG 31, 2026
$3,600,000
E
5 beds8.5 baths7,663 sq ft
8 Ridgeview Cir, Armonk, NY 10504
Listing by Compass Greater NY, LLC
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

$817,737

Est. take-home

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Refinance

Est. cash available

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Rent

$6,507/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

113.8%

0.3% MoM

Median sale price

$1.8M

$130K MoM

Avg. days on market

17d

2 days MoM

Recently sold homes

9 MoM

New listings for sale

OPEN SAT, 12:30PM TO 3PM
53 W Orchard Rd, Chappaqua, NY 10514
$1,725,000
4 beds3.5 baths3,581 sq ft
53 W Orchard Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
OPEN SUN, 12PM TO 2PM
$1,800,000
4 beds3.5 baths2,913 sq ft
406 Bedford Rd, Chappaqua, NY 10514
Listing by Howard Hanna Rand Realty
$1,325,000
3 beds3 baths2,238 sq ft
35 Marcourt Dr, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
See all

Provided by Redfin

Sale history for 369 Whippoorwill Rd

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #H6305280

Jun 24, 2024

Sold

$4,005,000

$542/sq ft

May 25, 2024

Pending

—

May 15, 2024

Listed

$3,850,000

$521/sq ft

OneKey® MLS as Distributed by MLS Grid #H6061379

Jan 15, 2021

Sold

$3,300,000

$446/sq ft

Aug 10, 2020

Listed

$3,495,000

$473/sq ft

Sophisticated Country!! The epitome of sophisticated living with a fresh, modern vibe. Stunning interior spaces with salvaged wood and reclaimed beams, artistic light fixtures, wide board white oak floors and a sophisticated palette. Over 7300 square feet of meticulous living space. Light Living Room with cast limestone fireplace. Dining Room with wood plank ceiling, pendant lamps and Phillip Jeffries wall covering. Chef’s Kitchen with Quartz counters and high-end appliances open to Family Room with floor-to-ceiling-concrete fireplace. Private and alluring Master Suite with spa Bath. Four additional Bedrooms. Gorgeous grounds with specimen plantings. Private Swimming Pool, built-in Barbecue and outdoor speakers perfect for outdoor living. Convenient location near the Saw Mill Parkway and Metro North trains. Absolutely turnkey! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,

HGMLS #4401768

Aug 4, 2014

Price Changed

$2,100,000

$284/sq ft

Aug 4, 2014

Sold

$2,100,000

$284/sq ft

May 1, 2014

Contingent

—

Apr 30, 2014

Price Changed

$2,150,000

$291/sq ft

Apr 3, 2014

Listed

$2,150,000

$291/sq ft

The architecture of today's homes continues to evolve in exciting and unexpected ways. This traditional center hall colonial exemplifies this attitude with an innovative attached pavilion styled pool house/year round entertainment space complete with 2nd kitchen and 2nd laundry. It also features billiards room, gym sauna and a Pitch n Put golf hole. Exudes quality. Celebrate being home in this lovely estate.

OneKey® MLS as Distributed by MLS Grid #H4401768

Aug 4, 2014

Sold

$2,100,000

$284/sq ft

Apr 3, 2014

Listed

$2,150,000

$291/sq ft

HGMLS #3307539

Nov 16, 2013

Delisted

—

May 16, 2013

Price Changed

Mar 14, 2013

Listed

OneKey® MLS as Distributed by MLS Grid #H3307539

Nov 15, 2013

Listing Removed

—

Mar 14, 2013

Listed

$2,495,000

$338/sq ft

HGMLS #3307421

Mar 14, 2013

Price Changed

Mar 14, 2013

Delisted

—

Mar 14, 2013

Listed

OneKey® MLS as Distributed by MLS Grid #H3307421

Mar 14, 2013

Listed

$2,695,000

$365/sq ft

Mar 14, 2013

Listing Removed

—

OneKey® MLS as Distributed by MLS Grid #H3218491

Mar 14, 2013

Listing Removed

—

Jun 8, 2012

Listed

$2,895,000

$392/sq ft

HGMLS #3218491

Nov 12, 2012

Delisted

—

Jun 8, 2012

Listed

Year

Property tax

Land + Additions

Assessment*

2026

$90,547 (+0.2%)

$125,000 + $420,500

$545,500

2025

$90,374 (+1.9%)

$125,000 + $420,500

$545,500

2024

$88,731 (+2.4%)

$125,000 + $420,500

$545,500

2023

$86,644 (+2.2%)

$125,000 + $420,500

$545,500

2022

$84,783 (+20.0%)

$125,000 + $420,500

$545,500

2021

$70,676 (+1.6%)

$125,000 + $420,500

$545,500

2020

$69,571 (−11.4%)

$125,000 + $333,400

$458,400

2019

$78,546

$125,000 + $333,400

$458,400

2018

$125,000 + $400,000

$525,000

2017

$125,000 + $313,750

$438,750

2016

$125,000 + $347,950

$472,950

2014

$125,000 + $420,500

$545,500

2013

$125,000 + $420,500

$545,500

2012

$125,000 + $420,500

$545,500

2011

$125,000 + $420,500

$545,500

2010

$125,000 + $420,500

$545,500

2009

$125,000 + $420,500

$545,500

2008

$125,000 + $420,500

$545,500

Tax history for 369 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$90,547 (+0.2%)

$125,000 + $420,500

$545,500

2025

$90,374 (+1.9%)

$125,000 + $420,500

$545,500

2024

$88,731 (+2.4%)

$125,000 + $420,500

$545,500

2023

$86,644 (+2.2%)

$125,000 + $420,500

$545,500

2022

$84,783 (+20.0%)

$125,000 + $420,500

$545,500

2021

$70,676 (+1.6%)

$125,000 + $420,500

$545,500

2020

$69,571 (−11.4%)

$125,000 + $333,400

$458,400

2019

$78,546

$125,000 + $333,400

$458,400

2018

$125,000 + $400,000

$525,000

2017

$125,000 + $313,750

$438,750

2016

$125,000 + $347,950

$472,950

2014

$125,000 + $420,500

$545,500

2013

$125,000 + $420,500

$545,500

2012

$125,000 + $420,500

$545,500

2011

$125,000 + $420,500

$545,500

2010

$125,000 + $420,500

$545,500

2009

$125,000 + $420,500

$545,500

2008

$125,000 + $420,500

$545,500

*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

2.11 Acres

Year renovated

—

Sq. Ft.

7,391

Year built

1994

Style

Single Family Residential

County

Westchester County

APN

553600A10101000020020020000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 30, 2026.

Property details

Parking

Parking Information
Parking Total: 3
Parking Features: Attached

Interior

Virtual Tour Information

Fireplace Information
Has Fireplace
Fireplaces Total: 2

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

Interior Features
Interior Features: Cathedral Ceiling(s),Chefs Kitchen,Eat-in Kitchen,Entrance Foyer,Formal Dining,First Floor Full Bath,High Ceilings,Kitchen Island,Primary Bathroom,Quartz/Quartzite Counters
Laundry Features: Inside
Appliances: Oil Water Heater
Levels: Two
Patio And Porch Features: Patio, Porch

Room Information
Basement YN: Yes
Attic: Pull Stairs
Rooms Total: 14
Basement: Full, Walk-Out Access
Additional Rooms: Loft,Office

Bathroom Information
Bathrooms Full: 5
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Clapboard, Frame
Waterfront YN: No

Pool Information
Pool Features: In Ground

Property Information
Stories: 2
Other Equipment: Generator
Living Area Source: Public Records
Property Sub Type: Single Family Residence
Property Condition: Actual

Financial

Tax Information
Tax Year: 2023
Tax Source: Municipality
Tax Annual Amount: $86,644

Financial Information
Buyer Financing: Cash

Utilities

Utility Information
Sewer: Septic Tank
Utilities: Trash Collection Private

Location

HOA Information
Association Amenities: Park, Sauna

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.: 7,391
Stories: —
Lot Size: 2.11 acres
Style: Single Family Residential
Year Built: 1994
Year Renovated: —
County: Westchester County
APN: 553600A10101000020020020000

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 • 0.8mi

10/10

Robert E Bell School

Public 5-8 • 1.5mi

9/10

Horace Greeley High School

Public 9-12 • 1.3mi

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

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

$3.93M – $4.75M

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New listings for sale in 10514

OPEN SAT, 12:30PM TO 3PM

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53 W Orchard Rd, Chappaqua, NY 10514

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Home values near 369 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
371 Whippoorwill Road, Chappaqua, NY 5 Beds \| 4.5 Baths \| 6410 Sq. Ft.	$2,757,324
363 Whippoorwill Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3450 Sq. Ft.	$1,835,657

Address	Redfin Estimate
365 Whippoorwill Road, Chappaqua, NY 5 Beds \| 6 Baths \| 6074 Sq. Ft.	$3,437,160
375 Whippoorwill Road, Chappaqua, NY 5 Beds \| 4 Baths \| 3478 Sq. Ft.	$1,896,637

Address	Redfin Estimate
370 Whippoorwill Road, Chappaqua, NY 6 Beds \| 3 Baths \| 7505 Sq. Ft.	$3,884,480
11 Sutton Farm Drive, Chappaqua, NY 5 Beds \| 6 Baths \| 5855 Sq. Ft.	$3,441,644

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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