Off market mar 2024 for $1.7M

$2,008,922

Est. refi paymentEst. refi $10,431/mo

•

4,834

sq ft

28 Flag Hill Rd, Chappaqua, NY 10514

About this home

Welcome to this stunning updated expanded ranch on a parklike property in desirable Chappaqua! 5+ bedrooms, office, and studio with a fully finished walk-out lower level, perfect for multi-generational living or those seeking flexible space for their needs. The bright new chef's kitchen is a masterpiece, featuring top-of-the-line appliances (SubZero, KitchenAid, Thermador), sleek countertops, and tremendous storage space. The spacious primary bedroom suite is a luxurious haven with a fireplace, 3 walk-in closets, dressing room, and large sunny bathroom. Step outside to the breathtaking heated freeform gunite pool with a hot tub and fire pit, surrounded by lush greenery and an outdoor kitchen. This oasis is truly an entertainer's dream with a summer kitchen/cabana providing the perfect backdrop for hosting gatherings and creating lasting memories. Two large decks offer additional outdoor entertainment and relaxation space, providing picturesque views of the surrounding beauty. Nestled in a peaceful cul de sac, this home offers the perfect balance of privacy and convenience. Enjoy the serenity of your surroundings while being just a short distance from town, schools, and the train station. Heated 3-car garage, new roof, and hot water heater. Discover the vibrant community of Chappaqua and Pleasantville with their charming shops, restaurants, and local amenities. Don't miss out on the opportunity to make this beautiful Chappaqua home your own! Additional Information: Amenities:Dressing Area,HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,

Single-familyProperty Type

1973Year Built

1.11 acresLot Size

$416Est. Price/Sq.Ft.

3 spacesParking

Listing by Hillary Landau • Compass Greater NY, LLC

Contact: (914) 238-0676

Bought with Sheri Wolfe • Berkshire Hathaway HS NY Prop

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6274384

Redfin Estimate

$2,008,922

$256K since sold in March 2024$5,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.2% higher than the average sale price ($1.64M) 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 OCT 30, 2026
$2,700,000
B
4 beds3.5 baths4,461 sq ft
10 Crestview Dr, Pleasantville, NY 10570
Listing by Julia B Fee Sothebys Int. Rlty
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 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

$558,525

Est. take-home

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Refinance

Est. cash available

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Rent

$5,261/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 28 Flag Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$28,917 (+1.2%)

$2,900 + $9,900

$12,800

2025

$28,560 (+1.4%)

$2,900 + $9,900

$12,800

2024

$28,175 (−2.1%)

$2,900 + $9,900

$12,800

2023

$28,789 (+3.2%)

$2,900 + $9,900

$12,800

2022

$27,886 (+7.5%)

$2,900 + $9,900

$12,800

2021

$25,932 (−2.4%)

$2,900 + $9,900

$12,800

2020

$26,573 (−13.3%)

$2,900 + $9,900

$12,800

2019

$30,638

$2,900 + $13,000

$15,900

2018

$2,900 + $13,000

$15,900

2017

$2,900 + $13,000

$15,900

2016

$2,900 + $13,000

$15,900

2014

$2,900 + $13,000

$15,900

2013

$2,900 + $13,000

$15,900

2012

$2,900 + $13,000

$15,900

2011

$2,900 + $13,000

$15,900

2010

$2,900 + $13,000

$15,900

2009

$2,900 + $13,000

$15,900

2008

$2,900 + $15,450

$18,350

Tax history for 28 Flag Hill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$28,917 (+1.2%)

$2,900 + $9,900

$12,800

2025

$28,560 (+1.4%)

$2,900 + $9,900

$12,800

2024

$28,175 (−2.1%)

$2,900 + $9,900

$12,800

2023

$28,789 (+3.2%)

$2,900 + $9,900

$12,800

2022

$27,886 (+7.5%)

$2,900 + $9,900

$12,800

2021

$25,932 (−2.4%)

$2,900 + $9,900

$12,800

2020

$26,573 (−13.3%)

$2,900 + $9,900

$12,800

2019

$30,638

$2,900 + $13,000

$15,900

2018

$2,900 + $13,000

$15,900

2017

$2,900 + $13,000

$15,900

2016

$2,900 + $13,000

$15,900

2014

$2,900 + $13,000

$15,900

2013

$2,900 + $13,000

$15,900

2012

$2,900 + $13,000

$15,900

2011

$2,900 + $13,000

$15,900

2010

$2,900 + $13,000

$15,900

2009

$2,900 + $13,000

$15,900

2008

$2,900 + $15,450

$18,350

*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

1.1 Acres

Year renovated

—

Sq. Ft.

3,064

Year built

1973

Style

Single Family Residential

County

Westchester County

APN

553489A09901400020100000000

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

Interior

Virtual Tour Information

Fireplace Information
Has Fireplace
Fireplaces Total: 2

Heating & Cooling
Cooling: Central Air
Heating: Hot Water, Oil

Interior Features
Interior Features: Built-in Features,Chefs Kitchen,Eat-in Kitchen,Entrance Foyer,Formal Dining,First Floor Bedroom,First Floor Full Bath,Kitchen Island,Master Downstairs,Primary Bathroom,Walk-In Closet(s)
Window Features: Blinds
Appliances: Convection Oven, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater
Flooring: Hardwood
Levels: Two
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Pull Stairs
Rooms Total: 12
Basement: Finished, Full, Walk-Out Access
Additional Rooms: Library/Den,Office

Bathroom Information
Bathrooms Full: 3
Bathrooms Half: 1

Exterior

Exterior Features
Exterior Features: Juliet Balcony, Mailbox
Construction Materials: Frame, Wood Siding
Other Structures: Outbuilding
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Cul-De-Sac

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: $28,789

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 Lane. Left onto Flag Hill Road. #28 on the left.
County Or Parish: Westchester County

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 3,064
Stories: —
Lot Size: 1.1 acres
Style: Single Family Residential
Year Built: 1973
Year Renovated: —
County: Westchester County
APN: 553489A09901400020100000000

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 • 2.5mi

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

$1.91M – $2.31M

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$900,000

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New listings for sale in 10514

OPEN SAT, 1PM TO 3PM

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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

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Home values near 28 Flag Hill Rd

Data from public records.

Address	Redfin Estimate
11 Flag Hill Rd, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2685 Sq. Ft.	$1,148,618
21 Flag Hill Rd, Chappaqua, NY 5 Beds \| 3 Baths \| 3113 Sq. Ft.	$1,590,611
18 Flag Hill Rd, Chappaqua, NY 3 Beds \| 2.5 Baths \| 2940 Sq. Ft.	$1,292,457
22 Flag Hill Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 3175 Sq. Ft.	$1,646,481
32 Flag Hill Rd, Chappaqua, NY 5 Beds \| 4 Baths \| 4200 Sq. Ft.	$1,588,678
425 Hardscrabble Rd, Briarcliff Manor, NY 4 Beds \| 3 Baths \| 2768 Sq. Ft.	$1,398,952
10 Deborah Ln, Chappaqua, NY 3 Beds \| 3 Baths \| 2821 Sq. Ft.	—

Address	Redfin Estimate
30 Flag Hill Rd, Chappaqua, NY 4 Beds \| 2.5 Baths \| 4019 Sq. Ft.	$1,607,976
20 Flag Hill Rd, Chappaqua, NY 4 Beds \| 3.5 Baths \| 4182 Sq. Ft.	$1,623,588
15 Flag Hill Rd Apt R0A, Chappaqua, NY 4 Beds \| 3 Baths \| 3569 Sq. Ft.	$1,627,581
27 Flag Hill Rd, Chappaqua, NY 5 Beds \| 3 Baths \| 3120 Sq. Ft.	$1,671,099
15 Flag Hill Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 3569 Sq. Ft.	$1,637,173
426 Hardscrabble Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 4953 Sq. Ft.	$2,055,647
3 Deborah Ln, Chappaqua, NY 4 Beds \| 3 Baths \| 2540 Sq. Ft.	$1,411,471

Address	Redfin Estimate
31 Flag Hill Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 3634 Sq. Ft.	$1,881,754
7 Flag Hill Rd, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2451 Sq. Ft.	$1,310,399
25 Flag Hill Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 3634 Sq. Ft.	$1,501,406
33 Flag Hill Rd, Chappaqua, NY 4 Beds \| 2 Baths \| 4515 Sq. Ft.	$1,824,753
5 Deborah Ln, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3791 Sq. Ft.	$1,458,249
2 Deborah Ln, Chappaqua, NY 3 Beds \| 2 Baths \| 2288 Sq. Ft.	$1,277,532
420 Hardscrabble Rd, Chappaqua, NY 4 Beds \| 4 Baths \| 2193 Sq. Ft.	$1,116,556

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2023. This data may not match . Learn more.

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