Off market jan 2025 for $1.2M

$1,590,611

Est. refi paymentEst. refi $8,872/mo

•

3,113

sq ft

21 Flag Hill Rd, Chappaqua, NY 10514

About this home

Chappaqua Schools. Spectacular mid-century 5 bedroom, 3 full bath home designed by noted architect Jack P. Fermery. Breathtaking views from the oversized deck and oversized windows on both levels. Large dine-in kitchen, dining room area and large living room with exposed brick fireplace. Primary bedroom/bath on first floor with 2 additional bedrooms. Lower level is walk out and has 2 bedrooms, large media room, oversized family room with gym and fireplace. Separate laundry room with shelving/closet. Walk out to yard from lower level affords easy entertaining with multi-level gathering spaces. The manageable shy 1 acre park-like lot is very private with specimen plantings, flowering shrubs and beautiful foliage. Minutes to town, schools, train, restaurants and situated on a private cul-de-sac. Do not miss this special offering. Additional Information: Amenities:Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1972Year Built

0.96 acresLot Size

$511Est. Price/Sq.Ft.

2 spacesParking

Listing by Wendy Nolan • Houlihan Lawrence Inc.

Listing by Helen Dorman • Houlihan Lawrence Inc.

Contact: 914-238-4766

Bought with Greg Gordon • Coldwell Banker Realty

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6332037

Redfin Estimate

$1,590,611

$311K since sold in January 2025$46K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.3% higher than the average sale price ($1.40M) of 6 comparable homes.

SOLD SEP 15, 2026
$1,550,000
A
4 beds3 baths3,334 sq ft
20 Robbins Rd, Pleasantville, NY 10570
Listing by North Country Sothebys Int Rlt
SOLD AUG 11, 2026
$2,000,000
B
4 beds3 baths3,340 sq ft
3 Banks Hill Rd, Pleasantville, NY 10570
Listing by Houlihan Lawrence Inc.
BOUGHT WITH REDFIN AUG 28, 2026
$1,300,501
C
4 beds3 baths2,814 sq ft
46 Bacon Hill Rd, Pleasantville, NY 10570
Listing by Houlihan Lawrence Inc.
SOLD JUN 1, 2026
$1,400,000
D
4 beds3 baths2,280 sq ft
55 Greenmeadow Rd, Pleasantville, NY 10570
Listing by Compass Greater NY, LLC
SOLD NOV 6, 2026
$970,000
E
3 beds3 baths3,375 sq ft
107 Stephenson Ter, Briarcliff Manor, NY 10510
Listing by ERA Insite Realty Services
SOLD OCT 1, 2026
$1,200,000
F
4 beds2.5 baths2,524 sq ft
1 Woodland Dr, Pleasantville, NY 10570
Listing by Coldwell Banker Realty

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Earn from this home

Sell

$507,225

Est. take-home

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Refinance

Est. cash available

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Rent

$5,306/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 21 Flag Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$24,937 (+3.8%)

$2,700 + $8,250

$10,950

2025

$24,024 (+2.0%)

$2,700 + $8,250

$10,950

2024

$23,558 (−2.0%)

$2,700 + $8,250

$10,950

2023

$24,038 (−3.6%)

$2,700 + $8,250

$10,950

2022

$24,926 (+7.6%)

$2,700 + $8,250

$10,950

2021

$23,168 (−27.3%)

$2,700 + $8,250

$10,950

2020

$31,879 (+2.2%)

$2,700 + $8,250

$10,950

2019

$31,195

$2,700 + $12,600

$15,300

2018

$2,700 + $12,600

$15,300

2017

$2,700 + $12,600

$15,300

2016

$2,700 + $12,600

$15,300

2014

$2,700 + $12,600

$15,300

2013

$2,700 + $12,600

$15,300

2012

$2,700 + $12,600

$15,300

2011

$2,700 + $12,600

$15,300

2010

$2,700 + $12,600

$15,300

2009

$2,700 + $12,600

$15,300

2008

$2,700 + $12,600

$15,300

Tax history for 21 Flag Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$24,937 (+3.8%)

$2,700 + $8,250

$10,950

2025

$24,024 (+2.0%)

$2,700 + $8,250

$10,950

2024

$23,558 (−2.0%)

$2,700 + $8,250

$10,950

2023

$24,038 (−3.6%)

$2,700 + $8,250

$10,950

2022

$24,926 (+7.6%)

$2,700 + $8,250

$10,950

2021

$23,168 (−27.3%)

$2,700 + $8,250

$10,950

2020

$31,879 (+2.2%)

$2,700 + $8,250

$10,950

2019

$31,195

$2,700 + $12,600

$15,300

2018

$2,700 + $12,600

$15,300

2017

$2,700 + $12,600

$15,300

2016

$2,700 + $12,600

$15,300

2014

$2,700 + $12,600

$15,300

2013

$2,700 + $12,600

$15,300

2012

$2,700 + $12,600

$15,300

2011

$2,700 + $12,600

$15,300

2010

$2,700 + $12,600

$15,300

2009

$2,700 + $12,600

$15,300

2008

$2,700 + $12,600

$15,300

*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

0.96 Acres

Year renovated

—

Sq. Ft.

3,113

Year built

1972

Style

Single Family Residential

County

Westchester County

APN

553489A09901400020170000000

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, Garage Door Opener

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 2

Heating & Cooling
Cooling: Wall/Window Unit(s)
Heating: Oil, Baseboard, Hot Water

Interior Features
Interior Features: Master Downstairs,First Floor Bedroom,First Floor Full Bath,Double Vanity,Eat-in Kitchen,Entrance Foyer,High Ceilings,Primary Bathroom,Pantry,Walk-In Closet(s),Built-in Features
Window Features: Screens, Oversized Windows, Skylight(s), Wall of Windows
Appliances: Oil Water Heater, Cooktop, Dishwasher, Dryer, Refrigerator, Washer
Levels: Two, Multi/Split
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Partial
Rooms Total: 10
Basement: Walk-Out Access, Finished, Full
Additional Rooms: Dining Area,Office,Media

Bathroom Information
Bathrooms Full: 3

Exterior

Exterior Features
Exterior Features: Balcony
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Near School, Near Shops, Cul-De-Sac, Near Public Transit, Views

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

Financial

Tax Information
Tax Year: 2024
Tax Source: Other
Tax Annual Amount: $23,558

Financial Information
Buyer Financing: Conventional

Utilities

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

Location

HOA Information
Association Amenities: Park

School Information
Elementary School: Roaring Brook
Middle Or Junior School: Robert E Bell School
High School: Horace Greeley High School
High School District: Chappaqua

Location Information
Hamlet: Chappaqua
Directions: Hardscrabble Rd to Deborah Lane to Flag Hill
County Or Parish: Westchester County

Public facts

Beds: 5
Baths: 3.0
Sq. Ft.: 3,113
Stories: —
Lot Size: 0.96 acres
Style: Single Family Residential
Year Built: 1972
Year Renovated: —
County: Westchester County
APN: 553489A09901400020170000000

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 • 0.6mi

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

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)

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

$1.51M – $1.83M

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Nearby similar homes

$900,000

Land— sq ft

765A Hardscrabble Rd, Chappaqua, NY 10514

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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

$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

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Home values near 21 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
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
22 Flag Hill Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3175 Sq. Ft.	$1,646,481
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
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
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
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
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

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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