Google street view image for 399 Bedford Rd, Chappaqua, NY 10514

Off market jan 1984 for $185K

$1,477,330

Est. refi paymentEst. refi $1,428/mo

•

4 ba

•

2,631

sq ft

399 Bedford Rd, Chappaqua, NY 10514

About this home

399 Bedford Rd is a 2,631 square foot house on a 1.24 acre lot with 3 bedrooms and 4 bathrooms. - it last sold on January 04, 1984 for $185,500. Based on Redfin's Chappaqua data, we estimate the home's value is $1,477,330.

Single-familyProperty Type

1955Year Built

1.24 acresLot Size

$562Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,477,330

$1.3M since sold in January 1984$56K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15.5% lower than the average sale price ($1.75M) of 6 comparable homes.

SOLD AUG 18, 2026
$1,510,000
A
3 beds2.5 baths2,010 sq ft
100 Devoe Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD JUL 13, 2026
$1,585,000
B
3 beds2.5 baths2,417 sq ft
148 Devoe Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD SEP 24, 2026
$2,020,000
C
4 beds3.5 baths3,124 sq ft
4 Old House Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD OCT 14, 2026
$1,820,000
D
3 beds4 baths3,140 sq ft
22 Garey Dr, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD FEB 27, 2026
$1,600,000
E
3 beds3.5 baths2,866 sq ft
36 Pond Hill Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
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

$1,390,447

Est. take-home

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Refinance

Est. cash available

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Rent

$5,298/mo

Redfin rental estimate

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Market trends in 10514, NY

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

111.3%

2.1% MoM

Median sale price

$1.6M

$140K MoM

Avg. days on market

17d

0 days MoM

Recently sold homes

6 MoM

New listings for sale

$829,000
3 beds2.5 baths1,600 sq ft
4 Hillside Pl, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
$1,396,000
3 beds2.5 baths2,420 sq ft
676 Hardscrabble Rd, Chappaqua, NY 10514
Listing by Corcoran Legends Realty
See all

Provided by Redfin

Sale history for 399 Bedford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$22,824 (+0.3%)

$37,200 + $102,800

$140,000

2025

$22,764 (+2.2%)

$37,200 + $102,800

$140,000

2024

$22,273 (+3.0%)

$37,200 + $102,800

$140,000

2023

$21,614 (+12.3%)

$37,200 + $102,800

$140,000

2022

$19,238 (+0.2%)

$37,200 + $102,800

$140,000

2021

$19,196 (+1.7%)

$37,200 + $102,800

$140,000

2020

$18,867 (+1.9%)

$37,200 + $102,800

$140,000

2019

$18,512

$37,200 + $102,800

$140,000

2018

$37,200 + $102,800

$140,000

2017

$37,200 + $102,800

$140,000

2016

$37,200 + $92,800

$130,000

2014

$37,200 + $92,800

$130,000

2013

$37,200 + $92,800

$130,000

2012

$37,200 + $92,800

$130,000

2011

$37,200 + $92,800

$130,000

2010

$37,200 + $92,800

$130,000

2009

$37,200 + $92,800

$130,000

2008

$37,200 + $92,800

$130,000

Tax history for 399 Bedford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$22,824 (+0.3%)

$37,200 + $102,800

$140,000

2025

$22,764 (+2.2%)

$37,200 + $102,800

$140,000

2024

$22,273 (+3.0%)

$37,200 + $102,800

$140,000

2023

$21,614 (+12.3%)

$37,200 + $102,800

$140,000

2022

$19,238 (+0.2%)

$37,200 + $102,800

$140,000

2021

$19,196 (+1.7%)

$37,200 + $102,800

$140,000

2020

$18,867 (+1.9%)

$37,200 + $102,800

$140,000

2019

$18,512

$37,200 + $102,800

$140,000

2018

$37,200 + $102,800

$140,000

2017

$37,200 + $102,800

$140,000

2016

$37,200 + $92,800

$130,000

2014

$37,200 + $92,800

$130,000

2013

$37,200 + $92,800

$130,000

2012

$37,200 + $92,800

$130,000

2011

$37,200 + $92,800

$130,000

2010

$37,200 + $92,800

$130,000

2009

$37,200 + $92,800

$130,000

2008

$37,200 + $92,800

$130,000

*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: 564
Basement Type: Full

Bathroom Information
# of Full Baths: 4

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 FARMS AMD
Living Sq. Ft: 2,631
Ground Floor Sq. Ft: 1,231
Building Sq. Ft: 2,631

Parking & Garage Information
# of Parking Spaces: 2
Parking Type: Basement Garage
Garage / Carport Type: Basement

Lot Information
# of Buildings: 1
Land Sq. Ft: 53,995
Legal Lot Number: 3
Legal Block Number: 1
School Tax District: CHAPPAQUA
Municipality Name: NEW CASTLE
Acres: 1.2396
Zoning Code: R-1A
State Use Description: SINGLE FAMILY RESID

Utility Information
Water Service Type: Commercial

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 3
Baths: 4.0
Sq. Ft.: 2,631
Stories: —
Lot Size: 1.24 acres
Style: Single Family Residential
Year Built: 1955
Year Renovated: —
County: Westchester County
APN: 553600A09301700010030000000

Home facts updated by county records on Sep 25, 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 • 1.1mi

10/10

Robert E Bell School

Public 5-8 • 1.3mi

9/10

Horace Greeley High School

Public 9-12 • 0.4mi

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

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 5 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 4.2 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.40M – $1.70M

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Nearby similar homes

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New listings for sale in 10514

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Listing by Corcoran Legends Realty

Home values near 399 Bedford Rd

Data from public records.

Address	Redfin Estimate
416 Bedford Rd, Chappaqua, NY 3 Beds \| 3 Baths \| 2356 Sq. Ft.	$1,395,768
395 Bedford Rd, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3041 Sq. Ft.	$1,987,673

Address	Redfin Estimate
405 Bedford Rd, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2965 Sq. Ft.	$1,324,074
391 Bedford Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 3019 Sq. Ft.	$1,826,853

Address	Redfin Estimate
403 Bedford Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 2141 Sq. Ft.	$1,369,677
382 Bedford Rd, Chappaqua, NY 5 Beds \| 4 Baths \| 3868 Sq. Ft.	$2,397,903

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