Google street view image for 22 Flag Hill Rd, Chappaqua, NY 10514

Off market

$1,646,481

•

3 ba

•

3,175

sq ft

22 Flag Hill Rd, Chappaqua, NY 10514

About this home

22 Flag Hill Rd is a 3,175 square foot house on a 1.05 acre lot with 4 bedrooms and 3 bathrooms. Based on Redfin's Chappaqua data, we estimate the home's value is $1,646,481.

Single-familyProperty Type

1996Year Built

1.05 acresLot Size

$519Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,646,481

$2,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.4% higher than the average sale price ($1.52M) of 6 comparable homes.

SOLD AUG 11, 2026
$2,000,000
A
4 beds3 baths3,340 sq ft
3 Banks Hill Rd, Pleasantville, NY 10570
Listing by Houlihan Lawrence Inc.
SOLD NOV 6, 2026
$970,000
B
3 beds3 baths3,375 sq ft
107 Stephenson Ter, Briarcliff Manor, NY 10510
Listing by ERA Insite Realty Services
SOLD SEP 15, 2026
$1,550,000
C
4 beds3 baths3,334 sq ft
20 Robbins Rd, Pleasantville, NY 10570
Listing by North Country Sothebys Int Rlt
SOLD JUL 31, 2026
$1,445,000
D
4 beds3.5 baths2,600 sq ft
31 Pierce Dr, Pleasantville, NY 10570
Listing by RE/MAX Prime Properties
SOLD OCT 1, 2026
$1,200,000
E
4 beds2.5 baths2,524 sq ft
1 Woodland Dr, Pleasantville, NY 10570
Listing by Coldwell Banker Realty
SOLD AUG 7, 2026
$1,950,000
F
4 beds3 baths2,953 sq ft
105 Cross Rdg, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC

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Earn from this home

Sell

$1,549,888

Est. take-home

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Rent

$5,158/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

OPEN SAT, 1PM TO 3PM
$2,150,000
5 beds4.5 baths4,278 sq ft
57 Random Farms Cir, Chappaqua, NY 10514
Listing by Serhant LLC
$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 22 Flag Hill Rd

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2026

$34,339 (+1.2%)

$1,950 + $13,250

$15,200

2025

$33,916 (+1.4%)

$1,950 + $13,250

$15,200

2024

$33,458 (−2.1%)

$1,950 + $13,250

$15,200

2023

$34,187 (−2.7%)

$1,950 + $13,250

$15,200

2022

$35,151 (+7.1%)

$1,950 + $13,250

$15,200

2021

$32,830 (+3.7%)

$1,950 + $13,250

$15,200

2020

$31,671 (+2.2%)

$1,950 + $13,250

$15,200

2019

$30,991

$1,950 + $13,250

$15,200

2018

$1,950 + $13,250

$15,200

2017

$1,950 + $13,250

$15,200

2016

$1,950 + $13,250

$15,200

2014

$1,950 + $13,250

$15,200

2013

$1,950 + $13,250

$15,200

2012

$1,950 + $13,250

$15,200

2011

$1,950 + $13,250

$15,200

2010

$1,950 + $13,250

$15,200

2009

$1,950 + $13,250

$15,200

2008

$1,950 + $13,250

$15,200

Tax history for 22 Flag Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$34,339 (+1.2%)

$1,950 + $13,250

$15,200

2025

$33,916 (+1.4%)

$1,950 + $13,250

$15,200

2024

$33,458 (−2.1%)

$1,950 + $13,250

$15,200

2023

$34,187 (−2.7%)

$1,950 + $13,250

$15,200

2022

$35,151 (+7.1%)

$1,950 + $13,250

$15,200

2021

$32,830 (+3.7%)

$1,950 + $13,250

$15,200

2020

$31,671 (+2.2%)

$1,950 + $13,250

$15,200

2019

$30,991

$1,950 + $13,250

$15,200

2018

$1,950 + $13,250

$15,200

2017

$1,950 + $13,250

$15,200

2016

$1,950 + $13,250

$15,200

2014

$1,950 + $13,250

$15,200

2013

$1,950 + $13,250

$15,200

2012

$1,950 + $13,250

$15,200

2011

$1,950 + $13,250

$15,200

2010

$1,950 + $13,250

$15,200

2009

$1,950 + $13,250

$15,200

2008

$1,950 + $13,250

$15,200

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Basement Information
Basement Sq. Ft: 1,323
Basement Type: Full

Bathroom Information
# of Full Baths: 3

Heating & Cooling
Air Conditioning Type: Central
Heating Type: Hot Water Steam

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Exterior Wall: Frame Wood

Property Information
Subdivision Name: CHAPPAQUA HEIGHTS
Living Sq. Ft: 3,175
Ground Floor Sq. Ft: 1,723
Building Sq. Ft: 4,498
Legal Description: CHAPPAQUA NY 2-87-9

Parking & Garage Information
Parking Type: Basement Garage
Garage / Carport Type: Basement

Lot Information
# of Buildings: 1
Land Sq. Ft: 45,912
Legal Lot Number: 9
Legal Block Number: 2
School Tax District: CHAPPAQUA
Municipality Name: MOUNT PLEASANT
Acres: 1.054
State Use Description: SINGLE FAMILY RESID

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 3,175
Stories: —
Lot Size: 1.05 acres
Style: Single Family Residential
Year Built: 1996
Year Renovated: —
County: Westchester County
APN: 553489A09901400020090000000

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.

Robert E Bell School

Public 5-8 • 1.2mi

9/10

Horace Greeley High School

Public 9-12 • 2.6mi

10/10

Bedford Road School

Public K-4 • 0.7mi

6/10

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

6 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)

34°

22°

37°

23°

54°

34°

63°

43°

71°

53°

82°

63°

86°

68°

82°

62°

78°

59°

66°

48°

55°

39°

40°

26°

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

$1.57M – $1.89M

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Nearby similar homes

$900,000

Land— sq ft

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New listings for sale in 10514

OPEN SAT, 1PM TO 3PM

$2,150,000

5 beds4.5 baths4,278 sq ft

57 Random Farms Cir, Chappaqua, NY 10514

Wooded backdrop • Soaring ceilings • Oversized windows

Listing by Serhant LLC

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4 beds3.5 baths3,164 sq ft

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Listing by William Raveis-New York, LLC

$799,000

2 beds2.5 baths1,244 sq ft

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Renovated condo • $625 HOA • Garage

Listing by Compass Greater NY, LLC

Home values near 22 Flag Hill Rd

Data from public records.

Address	Redfin Estimate
11 Flag Hill Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2685 Sq. Ft.	$1,148,618
21 Flag Hill Road, Chappaqua, NY 5 Beds \| 3 Baths \| 3113 Sq. Ft.	$1,590,611
7 Flag Hill Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2451 Sq. Ft.	$1,310,399
25 Flag Hill Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3634 Sq. Ft.	$1,501,406
32 Flag Hill Road, Chappaqua, NY 5 Beds \| 4 Baths \| 4200 Sq. Ft.	$1,588,678
425 Hardscrabble Road, Briarcliff Manor, NY 4 Beds \| 3 Baths \| 2768 Sq. Ft.	$1,398,952
2 Deborah Lane, Chappaqua, NY 3 Beds \| 2 Baths \| 2288 Sq. Ft.	$1,277,532

Address	Redfin Estimate
30 Flag Hill Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 4019 Sq. Ft.	$1,607,976
28 Flag Hill Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 4834 Sq. Ft.	$2,008,922
18 Flag Hill Road, Chappaqua, NY 3 Beds \| 2.5 Baths \| 2940 Sq. Ft.	$1,292,457
27 Flag Hill Road, Chappaqua, NY 5 Beds \| 3 Baths \| 3120 Sq. Ft.	$1,671,099
15 Flag Hill Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3569 Sq. Ft.	$1,637,173
426 Hardscrabble Road, Chappaqua, NY 4 Beds \| 3 Baths \| 4953 Sq. Ft.	$2,055,647
10 Deborah Lane, Chappaqua, NY 3 Beds \| 3 Baths \| 2821 Sq. Ft.	—

Address	Redfin Estimate
31 Flag Hill Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3634 Sq. Ft.	$1,881,754
20 Flag Hill Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 4182 Sq. Ft.	$1,623,588
15 Flag Hill Road Unit R0A, Chappaqua, NY 4 Beds \| 3 Baths \| 3569 Sq. Ft.	$1,627,581
33 Flag Hill Road, Chappaqua, NY 4 Beds \| 2 Baths \| 4515 Sq. Ft.	$1,824,753
5 Deborah Lane, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3791 Sq. Ft.	$1,458,249
400 Hardscrabble Road, Briarcliff Manor, NY 3 Beds \| 3 Baths \| 2701 Sq. Ft.	$1,232,095
3 Deborah Lane, Chappaqua, NY 4 Beds \| 3 Baths \| 2540 Sq. Ft.	$1,411,471

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