Google street view image for 27 Woodmill Rd, Chappaqua, NY 10514

Sold

$1,492,108

Est. refi paymentEst. refi $2,830/mo

•

2.5 ba

•

2,220

sq ft

27 Woodmill Rd, Chappaqua, NY 10514

About this home

Level, Wooded Property At End Of Cul-de-sac. Spacious Layout, Upgrades Move-in-condition.

Single-familyProperty Type

1959Year Built

1.8 acresLot Size

$672Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$1,492,108

$1.0M since sold in August 1998$22K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.7% lower than the average sale price ($1.67M) 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 SEP 24, 2026
$1,551,000
B
4 beds3 baths2,715 sq ft
50 Ludlow Dr, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD AUG 7, 2026
$1,950,000
C
4 beds3 baths2,953 sq ft
105 Cross Rdg, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD FEB 2, 2026
$1,375,000
D
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
E
4 beds2.5 baths2,892 sq ft
56 Cross Ridge Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JUN 26, 2026
$1,550,000
F
4 beds3 baths3,761 sq ft
39 Mayberry Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC

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Earn from this home

Sell

$1,404,376

Est. take-home

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Refinance

Est. cash available

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Rent

$4,641/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 27 Woodmill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$25,618 (+0.4%)

$40,000 + $109,500

$149,500

2025

$25,524 (+1.2%)

$40,000 + $109,500

$149,500

2024

$25,233 (+2.3%)

$40,000 + $109,500

$149,500

2023

$24,656 (+2.4%)

$40,000 + $109,500

$149,500

2022

$24,075 (+1.2%)

$40,000 + $109,500

$149,500

2021

$23,794 (+1.6%)

$40,000 + $109,500

$149,500

2020

$23,419 (+1.4%)

$40,000 + $109,500

$149,500

2019

$23,100

$40,000 + $109,500

$149,500

2018

$40,000 + $109,500

$149,500

2017

$40,000 + $109,500

$149,500

2016

$40,000 + $109,500

$149,500

2014

$40,000 + $109,500

$149,500

2013

$40,000 + $109,500

$149,500

2012

$40,000 + $109,500

$149,500

2011

$40,000 + $109,500

$149,500

2010

$40,000 + $109,500

$149,500

2009

$40,000 + $109,500

$149,500

2008

$40,000 + $109,500

$149,500

Tax history for 27 Woodmill Rd

Year

Property tax

Land + Additions

Assessment*

2026

$25,618 (+0.4%)

$40,000 + $109,500

$149,500

2025

$25,524 (+1.2%)

$40,000 + $109,500

$149,500

2024

$25,233 (+2.3%)

$40,000 + $109,500

$149,500

2023

$24,656 (+2.4%)

$40,000 + $109,500

$149,500

2022

$24,075 (+1.2%)

$40,000 + $109,500

$149,500

2021

$23,794 (+1.6%)

$40,000 + $109,500

$149,500

2020

$23,419 (+1.4%)

$40,000 + $109,500

$149,500

2019

$23,100

$40,000 + $109,500

$149,500

2018

$40,000 + $109,500

$149,500

2017

$40,000 + $109,500

$149,500

2016

$40,000 + $109,500

$149,500

2014

$40,000 + $109,500

$149,500

2013

$40,000 + $109,500

$149,500

2012

$40,000 + $109,500

$149,500

2011

$40,000 + $109,500

$149,500

2010

$40,000 + $109,500

$149,500

2009

$40,000 + $109,500

$149,500

2008

$40,000 + $109,500

$149,500

*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

2.5

Stories

—

Lot width

—

Lot depth

—

Lot size

1.8 Acres

Year renovated

—

Sq. Ft.

2,220

Year built

1959

Style

Single Family Residential

County

Westchester County

APN

553600A08101500010110000000

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.

Westorchard School

Public K-4 • 0.7mi

10/10

Seven Bridges Middle School

Public 5-8 • 0.8mi

8/10

Horace Greeley High School

Public 9-12 • 1.7mi

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

$1.42M – $1.72M

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New listings for sale in 10514

OPEN SUN, 12PM TO 2PM

$799,000

2 beds2.5 baths1,244 sq ft

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Listing by Compass Greater NY, LLC

Home values near 27 Woodmill Rd

Data from public records.

Address	Redfin Estimate
24 Woodmill Road, Chappaqua, NY 4 Beds \| 2 Baths \| 2457 Sq. Ft.	$1,297,716
31 Woodmill Road, Chappaqua, NY 3 Beds \| 2 Baths \| 2312 Sq. Ft.	$1,503,722
2 Woodmill Road, Chappaqua, NY 5 Beds \| 3.5 Baths \| 5227 Sq. Ft.	$1,844,526
16 Woodmill Road, Chappaqua, NY 3 Beds \| 2.5 Baths \| 2144 Sq. Ft.	$1,108,055
26 Mayberry Road, Chappaqua, NY 5 Beds \| 3 Baths \| 3200 Sq. Ft.	$1,744,702
299 Millwood Road, Chappaqua, NY 3 Beds \| 3 Baths \| 3645 Sq. Ft.	$1,639,193
301 Millwood Road, Chappaqua, NY 4 Beds \| 3.5 Baths \| 4061 Sq. Ft.	$1,924,438

Address	Redfin Estimate
11 Woodmill Road, Chappaqua, NY 5 Beds \| 4 Baths \| 4689 Sq. Ft.	$2,274,395
12 Woodmill Road, Chappaqua, NY 3 Beds \| 5.5 Baths \| 6123 Sq. Ft.	$2,893,053
23 Woodmill Road, Chappaqua, NY 3 Beds \| 3 Baths \| 5240 Sq. Ft.	$2,406,861
15 Woodmill Road, Chappaqua, NY 3 Beds \| 3 Baths \| 3736 Sq. Ft.	$1,545,671
31 Mayberry Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2168 Sq. Ft.	$1,526,194
305 Millwood Road, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2656 Sq. Ft.	$1,653,502
40 Mayberry Road, Chappaqua, NY 3 Beds \| 3 Baths \| 2564 Sq. Ft.	$1,337,231

Address	Redfin Estimate
35 Woodmill Road, Chappaqua, NY 4 Beds \| 4 Baths \| 4627 Sq. Ft.	$1,821,085
8 Woodmill Road, Chappaqua, NY 3 Beds \| 2.5 Baths \| 4457 Sq. Ft.	$1,683,551
19 Woodmill Road, Chappaqua, NY 4 Beds \| 3 Baths \| 3269 Sq. Ft.	$1,683,308
5 Woodmill Road, Chappaqua, NY 4 Beds \| 2 Baths \| 2294 Sq. Ft.	$1,251,825
1 Mayberry Lane, Chappaqua, NY 4 Beds \| 4.5 Baths \| 7973 Sq. Ft.	$2,998,391
6 Turner Drive South, Chappaqua, NY 4 Beds \| 4.5 Baths \| 4619 Sq. Ft.	$2,335,095
2 Turner Drive South, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2112 Sq. Ft.	$1,320,124

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