Google street view image for 1 Winthrop Rd, Chappaqua, NY 10514

Off market sep 1986 for $518K

$1,838,825

Est. refi paymentEst. refi $3,915/mo

•

3 ba

•

3,962

sq ft

1 Winthrop Rd, Chappaqua, NY 10514

About this home

1 Winthrop Rd is a 3,962 square foot house on a 2.07 acre lot with 4 bedrooms and 3 bathrooms. - it last sold on September 26, 1986 for $518,000. Based on Redfin's Chappaqua data, we estimate the home's value is $1,838,825.

Single-familyProperty Type

1964Year Built

2.07 acresLot Size

$464Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$1,838,825

$1.3M since sold in September 1986$28K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.5% higher than the average sale price ($1.76M) of 6 comparable homes.

SOLD OCT 14, 2026
$2,000,000
A
4 beds3 baths3,288 sq ft
12 Brandon Dr, Mount Kisco, NY 10549
Listing by Compass Greater NY, LLC
SOLD JUN 26, 2026
$1,550,000
B
4 beds3 baths3,761 sq ft
39 Mayberry Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD AUG 4, 2026
$1,754,000
C
4 beds3 baths3,834 sq ft
20 Cardinal Pl, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC
SOLD JUN 8, 2026
$1,480,000
D
4 beds3 baths3,331 sq ft
56 Brandon Dr, Mount Kisco, NY 10549
Listing by Keller Williams Realty Partner
SOLD JUN 17, 2026
$1,620,000
E
4 beds3.5 baths3,193 sq ft
25 Longview Ln, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD SEP 14, 2026
$2,155,000
F
4 beds3.5 baths3,010 sq ft
16 Fox Den Rd, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC

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Sell

$1,731,192

Est. take-home

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Refinance

Est. cash available

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Rent

$5,425/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

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

OPEN SUN, 12PM TO 2PM
$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 1 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2026

$38,351 (+0.4%)

$90,000 + $136,000

$226,000

2025

$38,185 (+1.2%)

$90,000 + $136,000

$226,000

2024

$37,715 (+2.4%)

$90,000 + $136,000

$226,000

2023

$36,815 (−0.5%)

$90,000 + $136,000

$226,000

2022

$37,010 (+18.3%)

$90,000 + $142,550

$232,550

2021

$31,277 (+1.7%)

$90,000 + $142,550

$232,550

2020

$30,766 (−4.2%)

$90,000 + $108,100

$198,100

2019

$32,120

$90,000 + $115,110

$205,110

2018

$90,000 + $115,110

$205,110

2017

$90,000 + $115,110

$205,110

2016

$90,000 + $115,110

$205,110

2014

$90,000 + $115,110

$205,110

2013

$90,000 + $115,110

$205,110

2012

$90,000 + $137,760

$227,760

2011

$90,000 + $137,760

$227,760

2010

$90,000 + $183,000

$273,000

2009

$90,000 + $183,000

$273,000

2008

$90,000 + $183,000

$273,000

Tax history for 1 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2026

$38,351 (+0.4%)

$90,000 + $136,000

$226,000

2025

$38,185 (+1.2%)

$90,000 + $136,000

$226,000

2024

$37,715 (+2.4%)

$90,000 + $136,000

$226,000

2023

$36,815 (−0.5%)

$90,000 + $136,000

$226,000

2022

$37,010 (+18.3%)

$90,000 + $142,550

$232,550

2021

$31,277 (+1.7%)

$90,000 + $142,550

$232,550

2020

$30,766 (−4.2%)

$90,000 + $108,100

$198,100

2019

$32,120

$90,000 + $115,110

$205,110

2018

$90,000 + $115,110

$205,110

2017

$90,000 + $115,110

$205,110

2016

$90,000 + $115,110

$205,110

2014

$90,000 + $115,110

$205,110

2013

$90,000 + $115,110

$205,110

2012

$90,000 + $137,760

$227,760

2011

$90,000 + $137,760

$227,760

2010

$90,000 + $183,000

$273,000

2009

$90,000 + $183,000

$273,000

2008

$90,000 + $183,000

$273,000

*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: 1,007
Basement Type: Full

Bathroom Information
# of Full Baths: 3

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

Fireplace Information
# of Fireplaces: 3
Has Fireplace

Exterior

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

Property Information
Living Sq. Ft: 3,962
Ground Floor Sq. Ft: 1,794
Building Sq. Ft: 3,962

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

Lot Information
# of Buildings: 1
Land Sq. Ft: 90,245
Legal Lot Number: 6
Legal Block Number: 2
School Tax District: CHAPPAQUA
Municipality Name: NEW CASTLE
Acres: 2.0717
Zoning Code: 03
State Use Description: SINGLE FAMILY RESID

Utility Information
Water Service Type: Commercial

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 3,962
Stories: —
Lot Size: 2.07 acres
Style: Single Family Residential
Year Built: 1964
Year Renovated: —
County: Westchester County
APN: 553600A08101900020060000000

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.

Roaring Brook School

Public K-4 • 0.8mi

10/10

Seven Bridges Middle School

Public 5-8 • 1.1mi

8/10

Horace Greeley High School

Public 9-12 • 1.2mi

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 99° expected this year, 15 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, 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

$1.75M – $2.12M

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New listings for sale in 10514

OPEN SUN, 12PM TO 2PM

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Home values near 1 Winthrop Rd

Data from public records.

Address	Redfin Estimate
5 Winthrop Road, Chappaqua, NY 4 Beds \| 2 Baths \| 3053 Sq. Ft.	$1,933,075
9 Winthrop Road, Chappaqua, NY 4 Beds \| 4 Baths \| 3962 Sq. Ft.	$1,968,131
21 Winthrop Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3950 Sq. Ft.	$1,824,663
11 Lawrence Farms Crossway, Chappaqua, NY 4 Beds \| 2.5 Baths \| 3932 Sq. Ft.	$1,849,907
75 Seven Bridges Road, Chappaqua, NY 4 Beds \| 4 Baths \| 2899 Sq. Ft.	$1,613,188
12 Lawrence Farms Crossway, Chappaqua, NY 5 Beds \| 4 Baths \| 3768 Sq. Ft.	$2,051,106
65 Seven Bridges Road, Chappaqua, NY 3 Beds \| 2 Baths \| 1606 Sq. Ft.	$1,114,649

Address	Redfin Estimate
17 Winthrop Road, Chappaqua, NY 4 Beds \| 4 Baths \| 4089 Sq. Ft.	$2,325,637
6 Winthrop Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3467 Sq. Ft.	$1,940,354
2 Hitching Post Lane, Chappaqua, NY 4 Beds \| 3.5 Baths \| 4229 Sq. Ft.	$2,026,527
1 Lawrence Farms Crossway, Chappaqua, NY 4 Beds \| 4 Baths \| 4567 Sq. Ft.	$2,191,793
59 Seven Bridges Road, Chappaqua, NY 3 Beds \| 2 Baths \| 2086 Sq. Ft.	$1,307,088
19 Lawrence Farms Crossway, Chappaqua, NY 4 Beds \| 2 Baths \| 2787 Sq. Ft.	$1,791,587
7 Lawrence Farms Crossway, Chappaqua, NY 4 Beds \| 4.5 Baths \| 5053 Sq. Ft.	$2,201,195

Address	Redfin Estimate
10 Winthrop Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3651 Sq. Ft.	$1,723,105
4 Winthrop Road, Chappaqua, NY 4 Beds \| 5 Baths \| 7010 Sq. Ft.	$2,821,060
63 Seven Bridges Road, Chappaqua, NY 5 Beds \| 4 Baths \| 3612 Sq. Ft.	$1,885,315
64 Seven Bridges Road, Chappaqua, NY 4 Beds \| 4 Baths \| 2970 Sq. Ft.	$1,540,781
8 Lawrence Farms Crossway, Chappaqua, NY 3 Beds \| 3.5 Baths \| 3155 Sq. Ft.	$1,913,239
71 Seven Bridges Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2380 Sq. Ft.	$1,283,254
23 Lawrence Farms Crossway, Chappaqua, NY 5 Beds \| 3.5 Baths \| 4584 Sq. Ft.	$1,978,785

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