Google street view image for 29 Windingwood Rd, Rye Brook, NY 10573

Sold

$1,168,913

Est. refi paymentEst. refi $5,443/mo

•

2.5 ba

•

2,100

sq ft

29 Windingwood Rd, Rye Brook, NY 10573

About this home

Totally Renovated Split Inside And Out. Almost Everything In This Home Has Been Redone In Last 2 Years. New Kitchen, Baths, Windows, Roof, Heating & Central Air, Bluestone Walkway & Porch, Driveway, Deck And More. If You Are Looking A Move Incondition Home In Rye Brook School District, Do Not Miss!!!!

Single-familyProperty Type

1957Year Built

0.3 acresLot Size

$557Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$1,168,913

$386K since sold in September 2007$12K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 19.7% lower than the average sale price ($1.46M) of 6 comparable homes.

SOLD JUN 1, 2026
$1,277,500
A
3 beds2.5 baths2,017 sq ft
4 Pine Ridge Rd, Rye Brook, NY 10573
Listing by Giner Real Estate Inc.
SOLD AUG 10, 2026
$1,379,000
B
4 beds2.5 baths2,176 sq ft
22 Paddock Rd, Rye Brook, NY 10573
Listing by Julia B Fee Sothebys Int. Rlty
SOLD AUG 14, 2026
$1,264,000
C
3 beds2.5 baths2,280 sq ft
2 Bell Pl, Rye Brook, NY 10573
Listing by Coldwell Banker Realty
SOLD SEP 29, 2026
$1,650,000
D
4 beds2.5 baths2,281 sq ft
3 Bonwit Rd, Rye Brook, NY 10573
Listing by Houlihan Lawrence Inc.
SOLD JUL 29, 2026
$1,655,000
E
3 beds2.5 baths2,080 sq ft
8 Fairlawn Pkwy, Rye Brook, NY 10573
Listing by Houlihan Lawrence Inc.
SOLD JUN 17, 2026
$1,510,000
F
3 beds2.5 baths1,818 sq ft
17 Old Orchard Rd, Rye Brook, NY 10573
Listing by Compass Greater NY, LLC

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Earn from this home

Sell

$1,099,733

Est. take-home

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Refinance

Est. cash available

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Rent

$5,002/mo

Redfin rental estimate

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Market trends in 10573, NY

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

105.9%

1.5% MoM

Median sale price

$937K

$12K MoM

Avg. days on market

25d

3 days MoM

Recently sold homes

6 MoM

New listings for sale

$319,000
Studio1 bath939 sq ft
1 Landmark Sq #203, Port Chester, NY 10573
Listing by ERA Insite Realty Services
$609,000
3 beds2 baths1,237 sq ft
552 Willett Ave, Port Chester, NY 10573
Listing by RE/MAX Prestige Properties
$1,495,000
4 beds3 baths2,538 sq ft
74 Tamarack Rd, Rye Brook, NY 10573
Listing by Compass Greater NY, LLC
$815,000
4 beds2 baths1,440 sq ft
551 King St, Port Chester, NY 10573
Listing by Compass Greater NY, LLC
$1,450,000
4 beds3.5 baths2,695 sq ft
19 Boxwood Pl, Rye Brook, NY 10573
Listing by Compass Greater NY, LLC
$899,000
6 beds2 baths2,360 sq ft
128 Touraine Ave, Port Chester, NY 10573
Listing by The Bridge Realty Group NY LLC
See all

Provided by Redfin

Sale history for 29 Windingwood Rd

Year

Property tax

Land + Additions

Assessment*

2026

$26,247 (+0.5%)

$465,800 + $502,700

$968,500

2025

$26,118 (+4.1%)

$465,800 + $502,700

$968,500

2024

$25,086 (+17.4%)

$465,800 + $447,800

$913,600

2023

$21,367 (+0.3%)

$443,600 + $434,900

$878,500

2022

$21,299 (+1.1%)

$443,600 + $385,200

$828,800

2021

$21,058 (+25.4%)

$443,600 + $331,000

$774,600

2020

$16,796 (+3.8%)

$443,600 + $331,000

$774,600

2019

$16,176

$376,500 + $333,200

$709,700

2018

$368,700 + $327,300

$696,000

2017

$364,200 + $324,400

$688,600

2016

$336,500 + $312,600

$649,100

2014

$282,600 + $292,000

$574,600

2013

$282,600 + $292,000

$574,600

2012

$302,100 + $287,700

$589,800

2011

$311,800 + $287,700

$599,500

2010

$153,900 + $541,200

$695,100

2009

$167,300 + $588,200

$755,500

2008

$172,500 + $606,400

$778,900

Tax history for 29 Windingwood Rd

Year

Property tax

Land + Additions

Assessment*

2026

$26,247 (+0.5%)

$465,800 + $502,700

$968,500

2025

$26,118 (+4.1%)

$465,800 + $502,700

$968,500

2024

$25,086 (+17.4%)

$465,800 + $447,800

$913,600

2023

$21,367 (+0.3%)

$443,600 + $434,900

$878,500

2022

$21,299 (+1.1%)

$443,600 + $385,200

$828,800

2021

$21,058 (+25.4%)

$443,600 + $331,000

$774,600

2020

$16,796 (+3.8%)

$443,600 + $331,000

$774,600

2019

$16,176

$376,500 + $333,200

$709,700

2018

$368,700 + $327,300

$696,000

2017

$364,200 + $324,400

$688,600

2016

$336,500 + $312,600

$649,100

2014

$282,600 + $292,000

$574,600

2013

$282,600 + $292,000

$574,600

2012

$302,100 + $287,700

$589,800

2011

$311,800 + $287,700

$599,500

2010

$153,900 + $541,200

$695,100

2009

$167,300 + $588,200

$755,500

2008

$172,500 + $606,400

$778,900

*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

0.3 Acres

Year renovated

1993

Sq. Ft.

2,100

Year built

1957

Style

Single Family Residential

County

Westchester County

APN

554805A13502600010070000000

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

Bruno M Ponterio Ridge Street School

Public K-5 • Assigned • 0.4mi

9/10

Blind Brook Rye Middle School

Public 6-8 • Assigned • 0.8mi

10/10

Blind Brook High School

Public 9-12 • Assigned • 0.8mi

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

5 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Rye Brook, NY • 10573

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 4.3 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

$1.11M – $1.35M

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New listings for sale in 10573

$319,000

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1 Landmark Sq #203, Port Chester, NY 10573

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Listing by RE/MAX Prestige Properties

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Listing by Compass Greater NY, LLC

$815,000

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Listing by Compass Greater NY, LLC

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Listing by Compass Greater NY, LLC

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6 beds2 baths2,360 sq ft

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Listing by The Bridge Realty Group NY LLC

Home values near 29 Windingwood Rd

Data from public records.

Address	Redfin Estimate
21 Windingwood Road North, Rye Brook, NY 3 Beds \| 3 Baths \| 1833 Sq. Ft.	$1,030,352
27 Windingwood Road North, Rye Brook, NY 3 Beds \| 2.5 Baths \| 2344 Sq. Ft.	$1,068,235
35 Windingwood Road North, Rye Brook, NY 4 Beds \| 3 Baths \| 3800 Sq. Ft.	$1,451,561
18 Windingwood Road North, Rye Brook, NY 4 Beds \| 3.5 Baths \| 2933 Sq. Ft.	$1,770,069
31 Windingwood Road North, Rye Brook, NY 3 Beds \| 2 Baths \| 2080 Sq. Ft.	$1,301,947
15 Churchill Road, Rye Brook, NY 3 Beds \| 2 Baths \| 1914 Sq. Ft.	$1,007,279
19 Churchill Road, Rye Brook, NY 4 Beds \| 2 Baths \| 2465 Sq. Ft.	$1,354,068

Address	Redfin Estimate
33 Windingwood Road North, Rye Brook, NY 3 Beds \| 3 Baths \| 2668 Sq. Ft.	$1,022,670
37 Windingwood Road North, Rye Brook, NY 4 Beds \| 3 Baths \| 1950 Sq. Ft.	$1,382,276
25 Windingwood Road North, Rye Brook, NY 3 Beds \| 2 Baths \| 1833 Sq. Ft.	$1,290,912
36 Windingwood Road North, Rye Brook, NY 4 Beds \| 2 Baths \| 2603 Sq. Ft.	$1,443,912
20 Paddock Road, Rye Brook, NY 3 Beds \| 2 Baths \| 1940 Sq. Ft.	$1,221,927
4 Latonia Road, Rye Brook, NY 4 Beds \| 2 Baths \| 2973 Sq. Ft.	$1,767,036
25 Churchill Road, Rye Brook, NY 3 Beds \| 2 Baths \| 2054 Sq. Ft.	$1,380,082

Address	Redfin Estimate
19 Windingwood Road North, Rye Brook, NY 3 Beds \| 2.5 Baths \| 2178 Sq. Ft.	$1,109,731
39 Windingwood Road North, Rye Brook, NY 5 Beds \| 3 Baths \| 3030 Sq. Ft.	$1,914,455
30 Windingwood Road North, Rye Brook, NY 3 Beds \| 2.5 Baths \| 1664 Sq. Ft.	$1,016,596
34 Windingwood Road North, Rye Brook, NY 3 Beds \| 2.5 Baths \| 2380 Sq. Ft.	$1,211,505
20 Churchill Road, Rye Brook, NY 4 Beds \| 3 Baths \| 2056 Sq. Ft.	$1,181,180
16 Churchill Road, Rye Brook, NY 3 Beds \| 2 Baths \| 2220 Sq. Ft.	$1,340,785
2 Latonia Road, Rye Brook, NY 3 Beds \| 2.5 Baths \| 1806 Sq. Ft.	$1,332,200

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