Google street view image for 5 Winthrop Rd, Chappaqua, NY 10514

Sold

$1,933,075

Est. refi paymentEst. refi $7,780/mo

•

2 ba

•

3,053

sq ft

5 Winthrop Rd, Chappaqua, NY 10514

About this home

Exquisite center hall colonial set on 1.69 acres with large, level backyard and wooded back drop. Cul-de-sac St. in a much desired neighborhood. Crown molding, wonderful built-ins. Wood flrs, mahogany deck and large patio. Lndry room on 1st floor. Powder room with marble mosaic tiles. Updated eat-in-kitchen with lovely granite counters and French drs out to large deck. C/O in progress for approx. 779 sq ft fnshd addtl space in lower level. Taxes do not reflect Star.

Single-familyProperty Type

1965Year Built

1.7 acresLot Size

$633Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$1,933,075

$538K since sold in February 2008$54K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 24.6% higher than the average sale price ($1.55M) 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 FEB 2, 2026
$1,375,000
B
4 beds2.5 baths2,541 sq ft
341 Millwood Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD MAY 11, 2026
$1,600,000
C
4 beds2.5 baths2,892 sq ft
56 Cross Ridge Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD MAY 6, 2026
$1,300,000
D
4 beds2.5 baths2,695 sq ft
37 Fox Den Rd, Mount Kisco, NY 10549
Listing by William Raveis-New York, LLC
SOLD APR 21, 2026
$1,655,800
E
4 beds2.5 baths2,932 sq ft
9 Whitlaw Ln, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD APR 20, 2026
$1,375,000
F
4 beds2.5 baths2,069 sq ft
111 Seven Bridges Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC

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Earn from this home

Sell

$1,820,032

Est. take-home

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Refinance

Est. cash available

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Rent

$5,123/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 5 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2026

$34,015 (+0.5%)

$39,600 + $160,400

$200,000

2025

$33,860 (+1.3%)

$39,600 + $160,400

$200,000

2024

$33,432 (+2.5%)

$39,600 + $160,400

$200,000

2023

$32,628 (+2.3%)

$39,600 + $160,400

$200,000

2022

$31,883 (+1.0%)

$39,600 + $160,400

$200,000

2021

$31,555 (+1.7%)

$39,600 + $160,400

$200,000

2020

$31,037 (−0.9%)

$39,600 + $160,400

$200,000

2019

$31,330

$39,600 + $160,400

$200,000

2018

$39,600 + $160,400

$200,000

2017

$39,600 + $160,400

$200,000

2016

$39,600 + $160,400

$200,000

2014

$39,600 + $160,400

$200,000

2013

$39,600 + $160,400

$200,000

2012

$39,600 + $160,400

$200,000

2011

$39,600 + $160,400

$200,000

2010

$39,600 + $160,400

$200,000

2009

$39,600 + $160,400

$200,000

2008

$39,600 + $160,400

$200,000

Tax history for 5 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2026

$34,015 (+0.5%)

$39,600 + $160,400

$200,000

2025

$33,860 (+1.3%)

$39,600 + $160,400

$200,000

2024

$33,432 (+2.5%)

$39,600 + $160,400

$200,000

2023

$32,628 (+2.3%)

$39,600 + $160,400

$200,000

2022

$31,883 (+1.0%)

$39,600 + $160,400

$200,000

2021

$31,555 (+1.7%)

$39,600 + $160,400

$200,000

2020

$31,037 (−0.9%)

$39,600 + $160,400

$200,000

2019

$31,330

$39,600 + $160,400

$200,000

2018

$39,600 + $160,400

$200,000

2017

$39,600 + $160,400

$200,000

2016

$39,600 + $160,400

$200,000

2014

$39,600 + $160,400

$200,000

2013

$39,600 + $160,400

$200,000

2012

$39,600 + $160,400

$200,000

2011

$39,600 + $160,400

$200,000

2010

$39,600 + $160,400

$200,000

2009

$39,600 + $160,400

$200,000

2008

$39,600 + $160,400

$200,000

*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

1.7 Acres

Year renovated

—

Sq. Ft.

3,053

Year built

1965

Style

Single Family Residential

County

Westchester County

APN

553600A08101900020050000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

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

4/10 Heat Factor

7 days above 99° 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

$1.84M – $2.22M

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New listings for sale in 10514

OPEN SUN, 12PM TO 2PM

$799,000

2 beds2.5 baths1,244 sq ft

13 Deer Run, Chappaqua, NY 10514

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Home values near 5 Winthrop Rd

Data from public records.

Address	Redfin Estimate
25 Winthrop Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 2312 Sq. Ft.	$1,661,832
1 Winthrop Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3962 Sq. Ft.	$1,838,825
4 Winthrop Road, Chappaqua, NY 4 Beds \| 5 Baths \| 7010 Sq. Ft.	$2,821,060
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
19 Lawrence Farms Crossway, Chappaqua, NY 4 Beds \| 2 Baths \| 2787 Sq. Ft.	$1,791,587
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
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
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
3 Alden Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3220 Sq. Ft.	$1,661,427
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
6 Winthrop Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 3467 Sq. Ft.	$1,940,354
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
12 Lawrence Farms Crossway, Chappaqua, NY 5 Beds \| 4 Baths \| 3768 Sq. Ft.	$2,051,106
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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