Off market mar 2019 for $900K

$1,623,588

Est. refi paymentEst. refi $3,852/mo

•

4,182

sq ft

20 Flag Hill Rd, Chappaqua, NY 10514

About this home

Welcome to 20 Flag Hill! Move right into this light filled, bright and young Colonial. Beautiful open floor plan. Freshly painted and newly refinished wood floors. Enjoy a large open kitchen with island and a 6 burner Dynasty commercial type range. The kitchen opens to family room with stone fireplace and built-ins. Entertain on a large wrap around deck with steps to a flat, useable yard. Master bedroom includes a fireplace, enormous walk in closet and cozy deck with distant views. Invisible fence and wired for a generator (included). Cul-de-sac location. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1996Year Built

0.99 acresLot Size

$388Est. Price/Sq.Ft.

2 spacesParking

Listing by Jeanne Coon • Houlihan Lawrence Inc.

Bought with Dalia Valdes • Julia B Fee Sothebys Int. Rlty

Redfin checked: a minute ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4846171

Redfin Estimate

$1,623,588

$724K since sold in March 2019$95K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.5% lower than the average sale price ($1.67M) of 6 comparable homes.

SOLD OCT 30, 2026
$2,700,000
A
4 beds3.5 baths4,461 sq ft
10 Crestview Dr, Pleasantville, NY 10570
Listing by Julia B Fee Sothebys Int. Rlty
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.
SOLD NOV 6, 2026
$970,000
C
3 beds3 baths3,375 sq ft
107 Stephenson Ter, Briarcliff Manor, NY 10510
Listing by ERA Insite Realty Services
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 SEP 15, 2026
$1,550,000
E
4 beds3 baths3,334 sq ft
20 Robbins Rd, Pleasantville, NY 10570
Listing by North Country Sothebys Int Rlt
SOLD JUL 31, 2026
$1,325,000
F
5 beds4 baths3,500 sq ft
302 Washington Ave, Pleasantville, NY 10570
Listing by William Raveis Real Estate

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Earn from this home

Sell

$920,309

Est. take-home

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Refinance

Est. cash available

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Rent

$5,571/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 20 Flag Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$27,110 (+1.2%)

$3,500 + $8,500

$12,000

2025

$26,775 (+1.4%)

$3,500 + $8,500

$12,000

2024

$26,414 (−2.1%)

$3,500 + $8,500

$12,000

2023

$26,990 (−2.7%)

$3,500 + $8,500

$12,000

2022

$27,751 (+7.1%)

$3,500 + $8,500

$12,000

2021

$25,919 (+3.7%)

$3,500 + $8,500

$12,000

2020

$25,003 (+2.2%)

$3,500 + $8,500

$12,000

2019

$24,466

$3,500 + $8,500

$12,000

2018

$3,500 + $8,500

$12,000

2017

$3,500 + $8,500

$12,000

2016

$3,500 + $8,500

$12,000

2014

$3,500 + $10,300

$13,800

2013

$3,500 + $10,300

$13,800

2012

$3,500 + $10,300

$13,800

2011

$3,500 + $10,300

$13,800

2010

$3,500 + $10,300

$13,800

2009

$3,500 + $14,900

$18,400

2008

$3,500 + $14,900

$18,400

Tax history for 20 Flag Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$27,110 (+1.2%)

$3,500 + $8,500

$12,000

2025

$26,775 (+1.4%)

$3,500 + $8,500

$12,000

2024

$26,414 (−2.1%)

$3,500 + $8,500

$12,000

2023

$26,990 (−2.7%)

$3,500 + $8,500

$12,000

2022

$27,751 (+7.1%)

$3,500 + $8,500

$12,000

2021

$25,919 (+3.7%)

$3,500 + $8,500

$12,000

2020

$25,003 (+2.2%)

$3,500 + $8,500

$12,000

2019

$24,466

$3,500 + $8,500

$12,000

2018

$3,500 + $8,500

$12,000

2017

$3,500 + $8,500

$12,000

2016

$3,500 + $8,500

$12,000

2014

$3,500 + $10,300

$13,800

2013

$3,500 + $10,300

$13,800

2012

$3,500 + $10,300

$13,800

2011

$3,500 + $10,300

$13,800

2010

$3,500 + $10,300

$13,800

2009

$3,500 + $14,900

$18,400

2008

$3,500 + $14,900

$18,400

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

Public record

Public record
Permits

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

0.98 Acres

Year renovated

—

Sq. Ft.

4,004

Year built

1995

Style

Single Family Residential

County

Westchester County

APN

553489A09901400020080000000

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

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 2

Heating & Cooling
Cooling: Attic Fan, Central Air
Heating: Forced Air, Oil

Interior Features
Interior Features: Cathedral Ceiling(s),Chandelier,Eat-in Kitchen,Entrance Foyer,Formal Dining,Primary Bathroom,Walk-In Closet(s)
Window Features: Blinds, Skylight(s), Storm Window(s)
Appliances: Dishwasher, Dryer, Refrigerator, Washer, Indirect Water Heater
Flooring: Carpet, Hardwood
Levels: Two
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Pull Stairs
Rooms Total: 10
Basement: Finished, Walk-Out Access

Bathroom Information
Bathrooms Full: 3
Bathrooms Half: 1

Exterior

Exterior Features
Exterior Features: Mailbox
Construction Materials: Frame, Wood Siding
Security Features: Security System
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Cul-De-Sac, Part Wooded, Sprinklers In Front, Sprinklers In Rear

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

Financial

Tax Information
Tax Year: 2018
Tax Source: Municipality
Tax Annual Amount: $24,124

Financial Information
Buyer Financing: Conventional

Utilities

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

Location

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 Road to Deborah and left onto Flag Hill.
County Or Parish: Westchester County

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 4,004
Stories: —
Lot Size: 0.98 acres
Style: Single Family Residential
Year Built: 1995
Year Renovated: —
County: Westchester County
APN: 553489A09901400020080000000

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

$1.54M – $1.87M

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Nearby similar homes

$900,000

Land— sq ft

765A Hardscrabble Rd, Chappaqua, NY 10514

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Listing by Howard Hanna Rand Realty

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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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Renovated condo • $625 HOA • Garage

Listing by Compass Greater NY, LLC

Home values near 20 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
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
28 Flag Hill Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 4834 Sq. Ft.	$2,008,922
15 Flag Hill Road #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 2018. This data may not match . Learn more.

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